OSMIUM-CONTAINING CONJUGATED POLYMER AND METHODS THEREOF

Abstract

An osmium-containing conjugated polymer and methods thereof. A structural formula of the osmium-containing conjugated polymer is formula I, a reaction formula of the osmium-containing conjugated polymer is a formula II.

Claims

1. An osmium-containing conjugated polymer, wherein: a repeating unit of the osmium-containing conjugated polymer consists of osmapentalyne groups, a conjugated linking group R.sub.1, and a vinyl group, a third position of an osmapentalyne group is connected to the conjugated linking group R.sub.1, and the conjugated linking group R.sub.1 is then connected to the vinyl group, and the vinyl group is connected to a seventh position of a next osmapentalyne group, and a structural formula of the osmium-containing conjugated polymer is as follows: ##STR00194## the [Os] is OsAL.sub.2, OsA.sub.2L, or OsL.sub.3, wherein A is at least one of —H, halogen group, —SCN, or —CN, and L is at least one of a phosphine ligand, a CO ligand, a pyridine ligand, a nitrogen heterocyclic carbene ligand, a nitrile ligand, or an isocyanic two-electron ligands, wherein the halogen group is at least one of —F, —Cl, —Br, or —I, the Y is at least one of CH.sub.2, O, C(COO(CH.sub.2).sub.kMe).sub.2, N, or S, wherein k is an integer between 0 and 18, the conjugated linking group R.sub.1 is at least one of a first substituted aryl group, a first unsubstituted aryl group, a substituted alkenyl group, an unsubstituted alkenyl group, a substituted alkynyl group, or an unsubstituted alkynyl group, wherein a substituted vinyl group or an unsubstituted vinyl group is a trans vinyl group when the substituted alkenyl group or the unsubstituted alkenyl group is the substituted vinyl group or the unsubstituted vinyl group, the Z.sup.− is an anion, and the m is an integer between 3 and 300.

2. The osmium-containing conjugated polymer according to claim 1, wherein the anion comprises at least one of F.sup.−, Cl.sup.−, Br.sup.−, I.sup.−, BF.sub.4.sup.−, H.sub.2PO.sub.4.sup.−, C.sub.2O.sub.4.sup.2−, SO.sub.4.sup.2−, CF.sub.3SO.sub.3.sup.−, CH.sub.3COO.sup.−, (CF.sub.3SO.sub.2).sub.2N.sup.−, NO.sub.3.sup.−, ClO.sub.4.sup.−, PF.sub.6.sup.−, or BPh.sub.4.sup.−.

3. The osmium-containing conjugated polymer according to claim 1, wherein: the L in the [Os] is at least one of triphenylphosphine, trimethylphosphine, triethylphosphine, tripropylphosphine, triisopropylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, methylpyridine, ethylpyridine, 1,4-bipyridine, 1,2-bis(4-pyridyl)ethylene, vinylpyridine, ethynyl Pyridine, pyridine boronic acid, aminopyridine, cyanopyridine, mercaptopyridine, dimethylaminopyridine, phenylpyridine, 1,2-bis(4-pyridyl)ethane, imidazole-type N-heterocyclic carbene, imidazoline-type N-heterocyclic carbene, thiazole-type N-heterocyclic carbene, triazol-type N-heterocyclic carbene, acetonitrile, propionitrile, benzonitrile, cyclohexyl isocyanide, tert-butyl isocyanide, or phenyl isocyanide, the L.sub.2 in the [Os] is integrated, and L.sub.2 is at least one of ethylenediamine, 2,2′-bipyridine, 1,10-phenanthroline, 1,1-bis(diphenylphosphine)methane, 1,2-bis (diphenylphosphine)ethane, 1,3-bis(diphenylphosphine)propane, ortho-phenylpyridine, or 8-hydroxyquinoline, and the AL.sub.2 in the [Os] is integrated, and the AL.sub.2 is at least one of a terpyridine, a PPP-type tridentate ligand, a PNP-type tridentate ligand, a PCP-type tridentate ligand, an NNN-type tridentate ligand, an NCN-type tridentate ligand, an NPN-type tridentate ligand, an ONO-type tridentate ligand, an OPO-type tridentate ligand, an OCO-type tridentate ligand, an SCS-type tridentate ligand, or a CCC-type tridentate ligand.

3. The osmium-containing conjugated polymer according to claim 1, wherein the first substituted aryl group or the first unsubstituted aryl group is at least one of phenyl, diphenyl, terphenyl, naphthyl, anthryl, fiki, pyrene, thienyl, dithienyl, terthienyl, dithienylethene, thiazolyl, thiadiazolyl, bis-thiadiazolyl, bis-terthienyl, furanyl, pyridyl, pyrrolyl, porphyrin, fluorenyl, bifluorenyl, terfluorenyl, carbazolyl, bicarbazolyl, tercarbazolyl, benzothiadiazolyl, tetrastyryl, hexabenzocoronyl, diketopyrrolopyrrole-based, benzodithienyl, indacenodithienyl, silyl fluorenyl, dithienocyclodecadiene, dithienosilole-based, dithienopyrrole-based, triphenylamino, naphthalenedithiadiazolyl, naphthalenetetracarboxylic diimide-based, perylenetetracarboxylic diimide-based, isoindigo-based, thienopyrroledione-based, benzopyrroledione-based, benzotriazolyl, thiadiazolobenzotriazolyl, pyridothiadiazolyl, or thieno[3,4-b]thienyl.

4. The osmium-containing conjugated polymer according to claim 1, wherein: a substituent reacts with an alkenyl group, the alkenyl group consists of 2-80 carbon atoms of a second substituted aryl group and a second unsubstituted aryl group, and the second substituted aryl group or the second unsubstituted aryl group is the same the first substituted aryl group or the first unsubstituted aryl group.

6. The osmium-containing conjugated polymer according to claim 1, wherein the conjugated linking group R1 is at least one of ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## wherein n is an integer between 0 and 30, and X is hydrogen, fluorine, amino, nitro, or alkoxy with 1-32 carbon atoms.

7. The osmium-containing conjugated polymer according to claim 1, wherein the osmium-containing conjugated polymer is at least one of ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251## ##STR00252## ##STR00253## ##STR00254## ##STR00255## ##STR00256## ##STR00257## ##STR00258## ##STR00259## ##STR00260## ##STR00261## ##STR00262## ##STR00263## ##STR00264## ##STR00265## ##STR00266## ##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271## ##STR00272## ##STR00273## ##STR00274## ##STR00275## ##STR00276## ##STR00277## ##STR00278## ##STR00279## ##STR00280## ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288## ##STR00289## ##STR00290## ##STR00291## ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296## ##STR00297## ##STR00298## ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313## wherein the [Os] is OsCl(PPh.sub.3).sub.2, n is an integer between 0 and 30, m is an integer between 3 and 300, and X is hydrogen, fluorine, amino, nitro, or alkoxy with 1-32 carbon atoms.

8. A method for preparing the osmium-containing conjugated polymer according to claim 1, comprising: dissolving a monomer of the osmium-containing conjugated polymer in an organic solvent; and processing a polymerization reaction under acidic conditions to obtain the osmium-containing conjugated polymer, wherein a reaction formula of the method is as follows: ##STR00314##

9. The method according to claim 8, wherein: an acid used in the acidic conditions comprises at least one of an inorganic acid or an organic acid, the inorganic acid comprises at least one of HClO.sub.4, HI, HBr, HCl, HNO.sub.3, H.sub.2SeO.sub.4, H.sub.2SO.sub.4, HClO.sub.3, H.sub.2C.sub.2O.sub.4, H.sub.2SO.sub.3, H.sub.3PO.sub.4, HNO.sub.2, HF, H.sub.2CO.sub.3, H.sub.2S, HClO, H.sub.3BO.sub.3, or H.sub.2SiO.sub.3, and the organic acid comprises at least one of CH.sub.3SO.sub.3H, CF.sub.3COOH, CCl.sub.3COOH, CHCl.sub.2COOH, CH.sub.3COOH, or HCOOH.

10. The method according to claim 8, comprising: terminating the polymerization reaction by a terminal alkyne substituted with a substituent of 2-80 carbon atoms, wherein the substituent comprises at least one of a third substituted aryl group, a third unsubstituted aryl group, a substituted alkyl group, an unsubstituted alkyl group, a substituted cycloalkyl group, or an unsubstituted cycloalkyl group.

11. A method, comprising: using the osmium-containing conjugated polymer according to claim 1 in organic optoelectronic devices.

12. A main chain comprising an osmapentalyne-containing conjugated polymer, wherein: a repeating unit of the osmapentalyne-containing conjugated polymer consists of a first group and a second group, the first group consists of a diosmapentalyne compound bridged with a conjugated linking group R.sub.1, the second group consists of a divinyl group bridged with a conjugated linking group R.sub.2, a specific structural formula of the repeating unit is as follows: ##STR00315## a 3rd position and a 3′rd position in the repeating unit are connected by the conjugated linking group R.sub.1, the divinyl group is connected to a 7th position and a 7′th position of the bis-diosmapentalyne compound; the [Os] is OsAL.sub.2, wherein A is at least one of —H, halogen, —SCN, or —CN, and L is at least one of a phosphine ligand, a CO ligand, a pyridine ligand, a nitrile ligand, or an isocyanide two-electron ligand, the Y is at least one of CH.sub.2, O, or C(COO(CH.sub.2).sub.kMe).sub.2, and k is an integer between 0 and 18, the conjugated linking group R.sub.1 is at least one of a first substituted aryl group, a first unsubstituted aryl group, a substituted alkenyl group, an unsubstituted alkenyl group, a substituted alkynyl group, or an unsubstituted alkynyl group, wherein a substituted vinyl group or an unsubstituted vinyl group is a trans vinyl group when the substituted alkenyl group or the unsubstituted alkenyl group is the substituted vinyl group or the unsubstituted vinyl group, the conjugated linking group R.sub.2 is at least one of the first substituted aryl group, the first unsubstituted aryl group, the substituted alkenyl group, the unsubstituted alkenyl group, the substituted alkynyl group, or the unsubstituted alkynyl group, wherein the substituted vinyl group or the unsubstituted vinyl group is the trans vinyl group when the substituted alkenyl group or the unsubstituted alkenyl group is the substituted vinyl group or the unsubstituted vinyl group, the Z.sup.− is an anion, and the m is an integer between 3 and 300.

13. The main chain comprising the osmapentalyne-containing conjugated polymer according to claim 12, wherein the anion comprises at least one of F.sup.−, Cl.sup.−, Br.sup.−, I.sup.−, BF.sub.4.sup.−, H.sub.2PO.sub.4.sup.−, C.sub.2O.sub.4.sup.2−, SO.sub.4.sup.2−, CF.sub.3SO.sub.3.sup.−, CH.sub.3COO.sup.−, (CF.sub.3SO.sub.2).sub.2N.sup.−, NO.sub.3.sup.−, ClO.sub.4.sup.−, PF.sub.6.sup.− or BPh.sub.4.sup.−.

14. The main chain comprising the osmapentalyne-containing conjugated polymer according to claim 12, wherein: the L in the [Os] is at least one of triphenylphosphine, trimethylphosphine, triethylphosphine, tripropylphosphine, triisopropylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, methylpyridine, ethylpyridine, 1,4-bipyridine, 1,2-bis(4-pyridyl)ethylene, vinylpyridine, ethynyl Pyridine, pyridine boronic acid, aminopyridine, cyanopyridine, mercaptopyridine, dimethylaminopyridine, phenylpyridine, 1,2-bis(4-pyridyl)ethane, acetonitrile, propionitrile, benzonitrile, cyclohexyl isocyanide, tert-butyl isocyanide, or phenyl isocyanide, or the L.sub.2 in the [Os] is integrated, and L.sub.2 is at least one of ethylenediamine, 2,2′-bipyridine, 1,10-phenanthroline, 1,1-bis(diphenylphosphine)methane, 1,2-bis (diphenylphosphine)ethane, 1,3-bis(diphenylphosphine)propane, ortho-phenylpyridine, 8-hydroxyquinoline, or terpyridine.

15. The main chain comprising the osmapentalyne-containing conjugated polymer according to claim 12, wherein: the substituted aryl group or the unsubstituted aryl group is at least one of phenyl, diphenyl, terphenyl, naphthyl, anthryl, fiki, pyrene, thienyl, dithienyl, terthienyl, dithienylethene, thiazolyl, thiadiazolyl, bis-thiadiazolyl, bis-terthienyl, furanyl, pyridyl, pyrrolyl, porphyrin, fluorenyl, bifluorenyl, terfluorenyl, carbazolyl, bicarbazolyl, tercarbazolyl, benzothiadiazolyl, tetrastyryl, hexabenzocoronyl, diketopyrrolopyrrole-based, benzodithienyl, indacenodithienyl, silyl fluorenyl, dithienocyclodecadiene, dithienosilole-based, dithienopyrrole-based, triphenylamino, naphthalenedithiadiazolyl, naphthalenetetracarboxylic diimide-based, perylenetetracarboxylic diimide-based, isoindigo-based, thienopyrroledione-based, benzopyrroledione-based, benzotriazolyl, thiadiazolobenzotriazolyl, pyridothiadiazolyl, or thieno[3,4-b]thienyl, and a substituent of the substituted aryl group or the unsubstituted aryl group comprises at least one of an alkyl with 1-28 carbon atoms, an alkoxy with 1-20 carbon atoms, an alkylthio with 1-20 carbon atoms, an acyl with 1-20 carbon atoms, an ester with 1-20 carbon atoms, an amino with 1-20 carbon atoms, an amide with 1-20 carbon atoms, an amide substituted with 2-20 carbon atoms, a cycloalkyl with 3-20 carbon atoms, an alkenyl with 1-20 carbon atoms, an alkynyl with 1-20 carbon atoms, nitro, cyano, or halogen.

16. The main chain comprising the osmapentalyne-containing conjugated polymer according to claim 12, wherein: the A in the [Os] is at least one of H, F, Cl, Br, or SCN, the L in the [Os] is at least one of a CO ligand, a triphenylphosphine ligand, a trimethylphosphine ligand, or a triethylphosphine ligand, the Z.sup.− is at least one of Cl.sup.−, Br.sup.−, BF.sub.4.sup.−, CF.sub.3SO.sub.3.sup.−, PF.sub.6.sup.−, or BPh.sub.4.sup.−, the conjugated linking group R.sub.1 is at least one of ##STR00316## ##STR00317## wherein n is an integer between 0 and 30, the conjugated linking group R.sub.2 is at least one of ##STR00318## ##STR00319## ##STR00320## ##STR00321## ##STR00322## ##STR00323## n is an integer between 0 and 30, and X is at least one of hydrogen, fluorine, amino, nitro, or alkoxy with 1-32 carbon atoms.

17. The main chain comprising an osmapentalyne-containing conjugated polymer according to claim 12, wherein: the main chain comprising an osmapentalyne-containing conjugated polymer is one of: ##STR00324## ##STR00325## ##STR00326## the [Os] is OsCl(PPh.sub.3).sub.2, n is an integer between 0 and 30, and m is an integer between 3 and 300.

18. A method for preparing the main chain comprising the osmapentalyne-containing conjugated polymer according to claim 12, comprising: dissolving bimetallic heterocyclic osmium heteropentylene and diacetylene monomers in an organic solvent, and a polymerization reaction occurs under acidic conditions to obtain the main chain comprising the osmapentalyne-containing conjugated polymer; the reaction formula is as follows: ##STR00327##

19. The method according to claim 18, wherein: an acid used in the acidic conditions comprises at least one of an inorganic acid or an organic acid, when the acid is the inorganic acid, the inorganic acid comprises at least one of HClO.sub.4, HI, HBr, HCl, HNO.sub.3, H.sub.2SeO.sub.4, H.sub.2SO.sub.4, HClO.sub.3, H.sub.2C.sub.2O.sub.4, H.sub.2SO.sub.3, H.sub.3PO.sub.4, HNO.sub.2, HF, H.sub.2CO.sub.3, H.sub.2S, HClO, H.sub.3BO.sub.3, or H.sub.2SiO.sub.3, and when the acid is the organic acid, the organic acid comprises at least one of CH.sub.3SO.sub.3H, CF.sub.3COOH, CCl.sub.3COOH, CHCl.sub.2COOH, CH.sub.3COOH, or HCOOH.

20. A method for using the main chain comprising the osmapentalyne-containing conjugated polymer according to claim 12, comprising: applying the main chain comprising the osmapentalyne-containing conjugated polymer in preparing organic optoelectronic devices.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0119] FIG. 1 illustrates a gel permeation chromatography (GPC) molecular weight distribution chart of an osmium-containing conjugated polymer I-1 of Embodiment 1 of the present disclosure.

[0120] FIG. 2 illustrates ultraviolet-visible absorption spectra of the osmium-containing conjugated polymer I-1 and an osmium-containing conjugated polymer I-383 of Embodiment 1 and Embodiment 3 of the present disclosure.

[0121] FIG. 3 illustrates a GPC molecular weight distribution chart (polystyrene is used as a standard sample, a test is performed in a pure N,N-dimethylformamide (DMF) mobile phase) of a main chain comprising an osmapentalyne-containing conjugated polymer P2 of Embodiment 12 of the present disclosure.

[0122] FIG. 4 illustrates ultraviolet-visible absorption spectra of a main chain comprising an osmapentalyne-containing conjugated polymer P8 and a main chain comprising an osmapentalyne-containing conjugated polymer P9 of Embodiment 18 and Embodiment 19 of the present disclosure.

[0123] FIG. 5 illustrates a cyclic voltammetry (CV) curve of a main chain comprising an osmapentalyne-containing conjugated polymer P14 of Embodiment 24 of the present disclosure.

DETAILED DESCRIPTION OF THE EMBODIMENTS

[0124] The present disclosure will be further described below through embodiments.

[0125] A formula M of osmapentalyne monomer used in the following embodiments is prepared in accordance with methods disclosed in a literature Zhuo, Q.; Lin, J.; Hua, Y.; Zhou, X.; Shao, Y.; Chen, S.; Chen, Z.; Zhu, J.; Zhang, H.; Xia, H.* Multiyne Chains Chelating Osmium via Three Metalcarbon σ Bonds. Nat. Commun. 2017, 8, 1912. and Wu, F.; Huang, W.; Zhuo, K.; Hua, Y.; Lin, J.; He, G.;* Chen, J.; Nie, L.;* Xia, H.* Carbolong Complexes as Photothermal Materials. Chin. J. Org. Chem. 2019, 39, 1743-1752.

Embodiment 1

[0126] ##STR00159##

[0127] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000),

##STR00160##

(phenylacetylene, which is purchased from Bailingwei Technology Co., Ltd., a trade name is 445058), and dichloromethane (DCM) used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0128] A method for preparing the osmium-containing conjugated polymer is as follows. An osmapentalyne monomer M1 (0.1 mmol) is dissolved in 5 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 0.5 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the osmapentalyne monomer M1 at room temperature (e.g., 20-25° C.) for 24 hours, the phenylacetylene is added to terminate the reaction, the reaction is performed at room temperature for another 2 hours, a large amount of ethyl ether is then added, a purple-red solid compound is precipitated and filtered, and the purple-red solid compound is repeatedly washed with ethyl ether and dried to obtain 90 mg of the osmium-containing conjugated polymer in purple-red color.

[0129] A data acknowledgement of a structure of the osmium-containing conjugated polymer is as follows: .sup.1H NMR (600.1 MHz, CD.sub.2Cl.sub.2): δ=6.81-7.78 (br, 53H), 6.23 (d, J=17.71 Hz, 1H), 5.79 (br, 2H), 3.00 (br, 2H), 2.08 (br, 2H), 1.62 (br, 2H); .sup.31P{.sup.1H}-NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=4.57 (br, CPPh.sub.3), −1.20 (br, OsPPh.sub.3).

[0130] A characterization data of a molecular weight of the osmium-containing conjugated polymer is as follows: a weight average molecular weight is 48227 Da, a number average molecular weight is 36989 Da, and a molecular weight distribution index of the osmium-containing conjugated polymer is 1.30.

[0131] In this embodiment, a gel permeation chromatography (GPC) molecular weight distribution chart of an osmium-containing conjugated polymer I-1 is illustrated in FIG. 1.

[0132] In this embodiment, an ultraviolet-visible absorption spectrum of the osmium-containing conjugated polymer I-1 is illustrated in FIG. 2.

Embodiment 2

[0133] ##STR00161##

[0134] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000),

##STR00162##

(phenylacetylene, which is purchased from Bailingwei Technology Co., Ltd., a trade name is 445058), and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0135] A method for preparing the osmium-containing conjugated polymer is as follows. An osmapentalyne monomer M2 (0.1 mmol) is dissolved in 5 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 0.5 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the osmapentalyne monomer M2 at room temperature (e.g., 20-25° C.) for 24 hours, the phenylacetylene is added to terminate the reaction, the reaction is performed at room temperature for another 2 hours, a large amount of ethyl ether is then added, a purple solid compound is precipitated and filtered, and the purple solid compound is repeatedly washed with ethyl ether and dried to obtain 92 mg of the osmium-containing conjugated polymer in purple-red color.

[0136] A data acknowledgement of a structure of the osmium-containing conjugated polymer is as follows: .sup.1H NMR (600.1 MHz, CD.sub.2Cl.sub.2): δ=6.81-7.98 (br, 53H), 6.23 (d, J=17.71 Hz, 1H), 5.82 (br, 2H), 5.17 (br, 2H), 4.30 (br, 2H); .sup.31P{.sup.1H}-NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=4.57 (br, CPPh.sub.3), −0.08 (br, OsPPh.sub.3).

[0137] A characterization data of a molecular weight of the osmium-containing conjugated polymer is as follows: a weight average molecular weight is 60383 Da, a number average molecular weight is 43130 Da, and a molecular weight distribution index of the osmium-containing conjugated polymer is 1.40.

Embodiment 3

[0138] ##STR00163##

[0139] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000),

##STR00164##

(phenylacetylene, which is purchased from Bailingwei Technology Co., Ltd., a trade name is 445058), and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0140] A method for preparing the osmium-containing conjugated polymer is as follows. An osmapentalyne monomer M3 (0.1 mmol) is dissolved in 5 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 0.5 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the osmapentalyne monomer M3 at room temperature (e.g., 20-25° C.) for 24 hours, the phenylacetylene is added to terminate the reaction, the reaction is performed at room temperature for another 2 hours, a large amount of ethyl ether is then added, a blue solid compound is precipitated and filtered, and the blue solid compound is repeatedly washed with ethyl ether and dried to obtain 95 mg of the osmium-containing conjugated polymer.

[0141] A data acknowledgement of a structure of the osmium-containing conjugated polymer is as follows: .sup.1H NMR (600.1 MHz, CD.sub.2Cl.sub.2): δ=6.83-7.85 (br, 46H), 5.97 (d, J=16.38 Hz, 1H), 5.82 (br, 1H), 5.17 (br, 2H), 4.30 (br, 2H); .sup.31P{.sup.1H}-NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=4.81 (br, CPPh.sub.3), −0.08 (br, OsPPh.sub.3).

[0142] A characterization data of a molecular weight is as follows: a weight average molecular weight is 52927 Da, a number average molecular weight is 39205 Da, and a molecular weight distribution index of the osmium-containing conjugated polymer is 1.35.

[0143] In this embodiment, an ultraviolet-visible absorption spectrum of the osmium-containing conjugated polymer I-383 is illustrated in FIG. 2.

Embodiment 4

[0144] ##STR00165##

[0145] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000),

##STR00166##

(phenylacetylene, which is purchased from Bailingwei Technology Co., Ltd., a trade name is 445058), and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0146] A method for preparing the osmium-containing conjugated polymer is as follows. An osmapentalyne monomer M4 (0.1 mmol) is dissolved in 5 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 0.5 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the osmapentalyne monomer M4 at room temperature (e.g., 20-25° C.) for 24 hours, the phenylacetylene is added to terminate the reaction, the reaction is performed at room temperature for another 2 hours, a large amount of ethyl ether is then added, a blue-purple solid compound is precipitated and filtered, and the blue-purple solid compound is repeatedly washed with ethyl ether and dried to obtain 95 mg of the osmium-containing conjugated polymer.

[0147] A data acknowledgement of a structure of the osmium-containing conjugated polymer is as follows: .sup.1H NMR (600.1 MHz, CD.sub.2Cl.sub.2): δ=6.83-7.85 (br, 46H), 5.97 (d, J=17.38 Hz, 1H), 5.82 (br, 2H), 3.01 (br, 2H), 2.07 (br, 2H), 1.65 (br, 2H); .sup.31P{.sup.1H}-NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=4.71 (br, CPPh.sub.3), −0.12 (br, OsPPh.sub.3).

[0148] A characterization data of a molecular weight of the osmium-containing conjugated polymer is as follows: a weight average molecular weight is 58220 Da, a number average molecular weight is 41005 Da, and a molecular weight distribution index of the osmium-containing conjugated polymer is 1.41.

Embodiment 5

[0149] ##STR00167##

[0150] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000),

##STR00168##

(phenylacetylene, which is purchased from Bailingwei Technology Co., Ltd., a trade name is 445058), and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0151] A method for preparing the osmium-containing conjugated polymer is as follows. An osmapentalyne monomer M5 (0.1 mmol) is dissolved in 5 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 0.5 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the osmapentalyne monomer M5 at room temperature (e.g., 20-25° C.) for 24 hours, the phenylacetylene is added to terminate the reaction, the reaction is performed at room temperature for another 2 hours, a large amount of ethyl ether is then added, a purple-black solid compound is precipitated and filtered, and the purple-black solid compound is repeatedly washed with ethyl ether and dried to obtain 93 mg of the osmium-containing conjugated polymer.

[0152] A data acknowledgement of a structure of the osmium-containing conjugated polymer is as follows: .sup.1H NMR (600.1 MHz, CD.sub.2Cl.sub.2): δ=6.93-8.31 (br, 52H), 5.84 (d, J=16.54 Hz, 1H), 5.17 (br, 2H), 3.73 (br, 2H), 0.70-1.40 (br, 26H); .sup.31P{.sup.1H}-NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=4.49 (br, CPPh.sub.3), −1.58 (br, OsPPh.sub.3).

[0153] A characterization data of a molecular weight of the osmium-containing conjugated polymer is as follows: a weight average molecular weight is 34642 Da, a number average molecular weight is 29357 Da, and a molecular weight distribution index of the osmium-containing conjugated polymer is 1.18.

Embodiment 6

[0154] ##STR00169##

[0155] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000),

##STR00170##

(phenylacetylene, which is purchased from Bailingwei Technology Co., Ltd., a trade name is 445058), and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0156] A method for preparing the osmium-containing conjugated polymer is as follows. An osmapentalyne monomer M6 (0.1 mmol) is dissolved in 5 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 0.5 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the osmapentalyne monomer M6 at room temperature (e.g., 20-25° C.) for 24 hours, the phenylacetylene is added to terminate the reaction, the reaction is performed at room temperature for another 2 hours, a large amount of ethyl ether is then added, a purple-black solid compound is precipitated and filtered, and the purple-black solid compound is repeatedly washed with ethyl ether and dried to obtain 92 mg of the osmium-containing conjugated polymer.

[0157] A data acknowledgement of a structure of the osmium-containing conjugated polymer is as follows: .sup.1H NMR (600.1 MHz, CD.sub.2Cl.sub.2): δ=6.48-8.31 (br, 52H), 6.25 (br, 1H), 3.11 (br, 2H), 2.37 (br, 2H), 1.24 (br, 2H), 0.72-1.40 (br, 26H); .sup.31P{.sup.1H}-NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=4.13 (br, CPPh.sub.3), −1.18 (br, OsPPh.sub.3).

[0158] A characterization data of a molecular weight of the osmium-containing conjugated polymer is as follows: a weight average molecular weight is 45633 Da, a number average molecular weight is 35931 Da, and a molecular weight distribution index of the osmium-containing conjugated polymer is 1.27.

Embodiment 7

[0159] ##STR00171##

[0160] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000),

##STR00172##

(phenylacetylene, which is purchased from Bailingwei Technology Co., Ltd., a trade name is 445058), and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0161] A method for preparing the osmium-containing conjugated polymer is as follows. An osmapentalyne monomer M7 (0.1 mmol) is dissolved in 5 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 0.5 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the osmapentalyne monomer M7 at room temperature (e.g., 20-25° C.) for 24 hours, the phenylacetylene is added to terminate the reaction, the reaction is performed at room temperature for another 2 hours, a large amount of ethyl ether is then added, a blue-green solid compound is precipitated and filtered, and the blue-green solid compound is repeatedly washed with ethyl ether and dried to obtain 89 mg of the osmium-containing conjugated polymer.

[0162] A data acknowledgement of a structure of the osmium-containing conjugated polymer is as follows: .sup.1H NMR (600.1 MHz, CD.sub.2Cl.sub.2): δ=6.98-7.87 (br, 46H), 6.08 (br, 1H), 5.19 (br, 2H), 4.39 (br, 2H); .sup.31P{.sup.1H}-NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=5.36 (s, CPPh.sub.3), 0.07 (s, OsPPh.sub.3).

[0163] A characterization data of a molecular weight of the osmium-containing conjugated polymer is as follows: a weight average molecular weight is 42622 Da, a number average molecular weight is 34761 Da, and a molecular weight distribution index of the osmium-containing conjugated polymer is 1.23.

Embodiment 8

[0164] ##STR00173##

[0165] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000),

##STR00174##

(phenylacetylene, which is purchased from Bailingwei Technology Co., Ltd., a trade name is 445058), and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0166] A method for preparing the osmium-containing conjugated polymer is as follows. An osmapentalyne monomer M8 (0.1 mmol) is dissolved in 5 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 0.5 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the osmapentalyne monomer M8 at room temperature (e.g., 20-25° C.) for 24 hours, the phenylacetylene is added to terminate the reaction, the reaction is performed at room temperature for another 2 hours, a large amount of ethyl ether is then added, a blue solid compound is precipitated and filtered, and the blue solid compound is repeatedly washed with ethyl ether and dried to obtain 91 mg of the osmium-containing conjugated polymer.

[0167] A data acknowledgement of a structure of the osmium-containing conjugated polymer is as follows: .sup.1H NMR (600.1 MHz, CD.sub.2Cl.sub.2): δ=6.98-7.83 (br, 49H), 6.08 (br, 1H), 6.50 (q, 1H), 6.24 (d, 1H), 5.71 (q, 1H), 5.54 (d, 1H), 4.66 (br, 2H), 3.87 (br, 2H); .sup.31P{.sup.1H}-NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=5.14 (s, CPPh.sub.3), −0.23 (s, OsPPh.sub.3).

[0168] A characterization data of a molecular weight of the osmium-containing conjugated polymer is as follows: a weight average molecular weight is 53567 Da, a number average molecular weight is 40023 Da, and a molecular weight distribution index of the osmium-containing conjugated polymer is 1.34.

Embodiment 9

[0169] ##STR00175##

[0170] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000),

##STR00176##

(phenylacetylene, which is purchased from Bailingwei Technology Co., Ltd., a trade name is 445058), and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0171] A method for preparing the osmium-containing conjugated polymer is as follows. An osmapentalyne monomer M9 (0.1 mmol) is dissolved in 5 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 0.5 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the osmapentalyne monomer M9 at room temperature (e.g., 20-25° C.) for 24 hours, the phenylacetylene is added to terminate the reaction, the reaction is performed at room temperature for another 2 hours, a large amount of ethyl ether is then added, a blue solid compound is precipitated and filtered, and the blue solid compound is repeatedly washed with ethyl ether and dried to obtain 93 mg of the osmium-containing conjugated polymer.

[0172] A data acknowledgement of a structure of the osmium-containing conjugated polymer is as follows: .sup.1H NMR (600.1 MHz, CD.sub.2Cl.sub.2): δ=6.48-8.31 (br, 52H), 6.25 (br, 2H), 5.97 (d, J=18.18 Hz, 1H), 3.12 (br, 2H), 2.36 (br, 2H), 1.22 (br, 2H), 0.72-1.40 (br, 26H); .sup.31P{.sup.1H}-NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=4.98 (br, CPPh.sub.3), −1.12 (br, OsPPh.sub.3).

[0173] A characterization data of a molecular weight of the osmium-containing conjugated polymer is as follows: a weight average molecular weight is 38978 Da, a number average molecular weight is 29986 Da, and a molecular weight distribution index of the osmium-containing conjugated polymer is 1.30.

[0174] A summary table of energy level information of all osmium-containing conjugated polymers in the above-mentioned embodiments is shown in Table 1.

TABLE-US-00001 TABLE 1 The summary table of the energy level information of osmium- containing conjugated polymers of the present disclosure EOX EHOMO ERED ELUMO Samples [V] [eV] [V] [eV] 1-1 0.94 −5.34 −0.68 −3.72 1-319 1.00 −5.40 −0.65 −3.75 1-490 0.98 −5.38 −0.67 −3.73 1-383 1.10 −5.50 −0.54 −3.86 PC70BM 1.54 −5.94 −0.51 −3.89

Embodiment 10

[0175] In the following examples, methods for preparing diosmapentalyne monomers M100-M300 are as follows, wherein polyacetylene carbon chains L1-L3 used as raw materials can be prepared in accordance with similar methods disclosed in Nat. Commun. 2017, 8, 1912. and Nat. Commun. 2020, 11, 4651.

##STR00177##

[0176] A method for preparing a diosmapentalyne monomer M100 is as follows: a polyacetylene carbon chain L1 (1.50 g, 3.55 mmol), triphenylphosphine (9.32 g, 35.5 mmol), and a tris(triphenylphosphine) osmium dichloride complex OsCl.sub.2(PPh.sub.3).sub.3 (11.18 g, 10.65 mmol) are dissolved in 80 mL of dichloromethane under a nitrogen atmosphere by a magnetic stirrer and reacted at room temperature (e.g., 20-25° C.) for 6 hours, a reaction solution is then concentrated to 15 mL and is added with 200 mL of ethyl ether, a solid product is precipitated and filtered, and the solid product is then washed with ethyl ether (e.g., 3×150 mL) several times. The solid product is further separated and purified through a silica gel column (a washing solution of dichloromethane and methanol with a volume ratio of 10:1 is used) to obtain 5.73 g of a tan solid product with a yield of 65%. A data acknowledgement of a structure of the diosmapentalyne monomer M100 is as follows: .sup.1H NMR plus .sup.1H-.sup.13C HSQC (600.1 MHz, CD.sub.2Cl.sub.2): δ=13.09 (s, 2H, C.sup.7H), 7.95-6.92 (94H, other aromatic protons), 5.95-5.79 (dd, J=16.55 Hz, J=78.83 Hz, 4H, C.sup.11H and C.sup.10H), 4.67 (s, 4H, C.sup.9H), 3.85 ppm (s, 4H, C.sup.8H). .sup.31P NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=6.11 (t, J.sub.P—P=5.86 Hz, CPPh.sub.3), 2.68 ppm (d, J.sub.P—P=5.86 Hz, OsPPh.sub.3). .sup.13C NMR plus DEPT-135, .sup.1H-.sup.13C HSQC and .sup.1H-.sup.13C HMBC (150.9 MHz, CD.sub.2Cl.sub.2): δ=318.1 (dt, apparent q, J.sub.P—C=12.91 Hz, J.sub.P—C=12.91 Hz, C.sup.1), 210.6 (m, C.sup.7), 172.2 (s, C.sup.5), 171.5 (s, C.sup.6), 168.8 (d, J.sub.P—C=22.27 Hz, C.sup.4), 161.7 (d, J.sub.P—C=15.26 Hz, C.sup.3), 136.6 (s, C.sup.10), 125.3 (s, C.sup.11), 73.66 (s, C.sup.8), 68.80 (s, C.sup.9), 135.7-119.4 ppm (other aromatic carbons). Elemental analysis calculated (%) for C.sub.136H.sub.108Cl.sub.4O.sub.2Os.sub.2P.sub.6: C, 65.80, H, 4.39; found: C, 65.67, H, 4.25. HRMS (ESI): m/z calculated for [C.sub.136H.sub.108Cl.sub.2O.sub.2Os.sub.2P.sub.6].sup.2+, 1205.2674; found, 1205.2845.

##STR00178##

[0177] A method for preparing a diosmapentalyne monomer M200 is as follows: a polyacetylene carbon chain L2 (1.50 g, 3.36 mmol), triphenylphosphine (8.83 g, 33.6 mmol), and a tris(triphenylphosphine) osmium dichloride complex OsCl.sub.2(PPh.sub.3).sub.3 (10.58 g, 10.08 mmol) are dissolved in 120 mL of dichloromethane under a nitrogen atmosphere by a magnetic stirrer and reacted at room temperature (e.g., 20-25° C.) for 6 hours, a reaction solution is then concentrated to 15 mL and is added with 180 mL of ethyl ether, a solid product is precipitated and filtered, and the solid product is then washed with ethyl ether (e.g., 3×120 mL) several times. The solid product is further separated and purified through a silica gel column (a washing solution of dichloromethane and methanol with a volume ratio of 10:1 is used) to obtain 6.06 g of a tan solid product with a yield of 72%. A data acknowledgement of a structure of the monomer of the diosmapentalyne monomer M200 is as follows: .sup.1H NMR plus .sup.1H-.sup.13C HSQC (600.1 MHz, CD.sub.2Cl.sub.2): δ=13.11 (s, 2H, C.sup.7H), 7.89-6.19 (98H, other aromatic protons), 4.61 (s, 4H, C.sup.9H), 3.23 ppm (s, 4H, C.sup.8H). .sup.31P NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=5.96 (s, CPPh.sub.3), 3.01 ppm (s, OsPPh.sub.3). .sup.13C NMR plus DEPT-135, .sup.1H-.sup.13C HSQC and .sup.1H-.sup.13C HMBC (150.9 MHz, CD.sub.2Cl.sub.2): δ=317.9 (s, C.sup.1), 210.7 (s, C.sup.7), 173.2 (s, C.sup.5), 171.9 (s, C.sup.6), 166.6 (s, C.sup.4), 164.9 (s, C.sup.3), 73.03 (s, C.sup.8), 68.56 (s, C.sup.9), 140.0-119.7 ppm (other aromatic carbons). Elemental analysis calculated (%) for C.sub.138H.sub.108Cl.sub.4O.sub.2Os.sub.2P.sub.6: C, 66.13, H, 4.34; found: C, 66.34, H, 4.25. HRMS (ESI): m/z calculated for [C.sub.138H.sub.108Cl.sub.2O.sub.2Os.sub.2P.sub.6].sup.2+, 1217.2674; found, 1217.2823.

##STR00179##

[0178] A method for preparing a diosmapentalyne monomer M300 is as follows: a polyacetylene carbon chain L3 (1.50 g, 3.59 mmol), triphenylphosphine (9.43 g, 35.9 mmol), and a tris(triphenylphosphine) osmium dichloride complex OsCl.sub.2(PPh.sub.3).sub.3 (11.31 g, 10.77 mmol) are dissolved in 120 mL of dichloromethane under a nitrogen atmosphere by a magnetic stirrer and reacted at room temperature (e.g., 20-25° C.) for 6 hours, a reaction solution is then concentrated to 15 mL and is added with 180 mL of ethyl ether, a solid product is precipitated and filtered, and the solid product is then washed with ethyl ether (e.g., 3×120 mL) several times. The solid product is further separated and purified through a silica gel column (a washing solution of dichloromethane and methanol with a volume ratio of 10:1 is used) to obtain 6.05 g of a tan solid product with a yield of 68%. A data acknowledgement of a structure of the diosmapentalyne monomer M300 is as follows: .sup.1H NMR plus .sup.1H-.sup.13C HSQC (600.1 MHz, CD.sub.2Cl.sub.2): δ=13.15 (s, 2H, C.sup.7H), 7.91-6.88 (94H, other aromatic protons), 6.19 (d, J=16.71 Hz, 2H, C.sup.11H), 5.73 (d, J=16.71 Hz, 2H, C.sup.10H), 2.57 (m, 4H, C.sup.9H), 1.99 (m, 4H, C.sup.12H), 1.81 (t, J=7.26 Hz, 4H, C.sup.8H). .sup.31P NMR (242.9 MHz, CD.sub.2Cl.sub.2): δ=5.89 (t, J.sub.P—P=5.85 Hz, CPPh.sub.3), 3.53 ppm (s, OsPPh.sub.3). .sup.13C NMR plus DEPT-135, .sup.1H-.sup.13C HSQC and .sup.1H-.sup.13C HMBC (150.9 MHz, CD.sub.2Cl.sub.2): δ=318.5 (dt, apparent q, J.sub.P—C=13.16 Hz, J.sub.P—C=13.16 Hz, C.sup.1), 215.0 (m, C.sup.7), 179.1 (s, C.sup.5), 175.8 (s, C.sup.6), 170.9 (d, J.sub.P—C=22.23 Hz, C.sup.4), 160.0 (d, J.sub.P—C=15.53 Hz, C.sup.3), 135.8 (s, C.sup.10), 126.6 (s, C.sup.11), 36.43 (s, C.sup.8), 29.75 (s, C.sup.9), 29.62 (s, C.sup.12), 135.5-120.1 ppm (other aromatic carbons). Elemental analysis calculated (%) for C.sub.138H.sub.112Cl.sub.4Os.sub.2P.sub.6: C, 66.88, H, 4.55; found: C, 66.74, H, 4.73. HRMS (ESI): m/z calculated for [C.sub.138H.sub.112Cl.sub.2Os.sub.2P.sub.6].sup.2+, 1203.2881; found, 1203.3015.

Embodiment 11

[0179] ##STR00180##

[0180] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), 1,4-Diethynylbenzene E1 is purchased from Bailingwei Technology Co., Ltd., a trade name is 009135, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0181] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P1 is as follows. The diosmapentalyne monomer M100 (0.08 mmol) and the 1,4-diethynylbenzene (0.081 mmol) are dissolved in 10 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 1 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M100 at room temperature (e.g., 20-25° C.) for 5 hours, a large amount of ethyl ether is then added, a blue solid compound is precipitated and filtered, and the blue solid compound is repeatedly washed with ethyl ether and dried to obtain 188 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P1.

[0182] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P1 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=5.81 (br, 6H, C.sup.10H, C.sup.11H, and C.sup.13H), 5.15 (br, 4H, C.sup.9H), 4.32 (br, 4H, C.sup.8H), 7.86-7.09 ppm (100H, other aromatic protons and C.sup.12H). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.81 (s, CPPh.sub.3), 0.02 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.1 (s, C.sup.1), 217.4 (s, C.sup.7), 172.4 (s, C.sup.5), 169.4 (s, C.sup.6), 168.1 (s, C.sup.4), 159.5 (s, C.sup.3), 83.92 (end-capper alkyne), 78.67 (end-capper alkyne), 74.26 (m, C.sup.8), 70.93 (s, C.sup.9), 143.5-112.8 ppm (other aromatic carbons).

[0183] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P1 is as follows: polystyrene is used as a standard sample, and a weight average molecular weight measured in a N,N-dimethylformamide (DMF) solvent is 219448 Da, a number average molecular weight is 161669 Da, and a molecular weight distribution index is 1.36.

Embodiment 12

[0184] ##STR00181##

[0185] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E2 is synthesized according to the method reported in Organometallics, 2001, 20(11), 2262-2269, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0186] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P2 is as follows. The diosmapentalyne monomer M100 (0.10 mmol) and the diacetylene E2 (0.101 mmol) are dissolved in 12 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 1.2 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added, a large amount of ethyl ether is then added, a purple solid compound is precipitated and filtered, and the purple solid compound is repeatedly washed with ethyl ether and dried to obtain 252 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P2 shown in FIG. 3.

[0187] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P2 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=5.92 (br, 4H, C.sup.10H and C.sup.11H), 5.62 (s, 2H, C.sup.13H), 5.18 (br, 4H, C.sup.9H), 4.36 (br, 4H, C.sup.8H), 2.08 (s, 4H, CH.sub.2C.sub.5H.sub.11), 1.14 (s, 16H, CH.sub.2C.sub.4H.sub.8CH.sub.3), 0.76 (s, 6H, CH.sub.3), 7.86-7.10 ppm (102H, other aromatic protons and C.sup.12H). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.73 (s, CPPh.sub.3), 0.01 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.4 (s, C.sup.1), 218.7 (s, C.sup.7), 172.3 (s, C.sup.5), 168.9 (s, C.sup.6), 167.6 (d, J.sub.P—C=20.59 Hz, C.sup.4), 158.5 (d, J.sub.P—C=13.52 Hz, C.sup.3), 73.69 (s, C.sup.8), 71.00 (s, C.sup.9), 55.21 (s, C.sup.14), 40.31 (m), 31.78 (m), 29.78 (m), 23.92 (m), 22.61 (m), 13.80 (m), 163.4-112.4 ppm (other aromatic carbons).

[0188] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P2 is as follows: polystyrene is used as a standard sample, and a weight average molecular weight measured in a N,N-dimethylformamide (DMF) solvent is 308091 Da, a number average molecular weight is 209196 Da, and a molecular weight distribution index is 1.47.

Embodiment 13

[0189] ##STR00182##

[0190] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E3 is purchased from Beijing Huaweiruike Chemical Co., Ltd. with a product number of 2135944-48-6, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0191] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P3 is as follows. The diosmapentalyne monomer M100 (0.09 mmol) and the diacetylene E3 (0.091 mmol) are dissolved in 10 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 1 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M100 at room temperature (e.g., 20-25° C.) for 2 hours, a large amount of ethyl ether is then added, a blue-purple solid compound is precipitated and filtered, and the blue-purple solid compound is repeatedly washed with ethyl ether and dried to obtain 224 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P3.

[0192] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P3 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=6.06-5.96 (m, 4H, C.sup.10H and C.sup.11H), 5.66 (s, 2H, C.sup.13H), 5.24 (br, 4H, C.sup.9H), 4.55 (br, 1H, C.sup.14H), 4.35 (br, 4H, C.sup.8H), 2.03 (s, 4H, CH.sub.2C.sub.7H.sub.15), 1.16 (m, 24H, CH.sub.2C.sub.6H.sub.12CH.sub.3), 0.83 (s, 6H, CH.sub.3), 7.85-7.10 ppm (102H, other aromatic protons and C.sup.12H). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.71 (s, CPPh.sub.3), 0.30 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.5 (s, C.sup.1), 218.9 (s, C.sup.7), 172.4 (s, C.sup.5), 168.8 (s, C.sup.6), 167.5 (s, C.sup.4), 158.2 (s, C.sup.3), 74.01 (m, C.sup.8), 71.00 (s, C.sup.9), 57.08 (s, C.sup.14), 33.82, 31.71, 29.43, 29.15, 27.29, 26.92, 22.56, 13.85, 163.4-107.8 ppm (other aromatic carbons).

[0193] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P3 is as follows: polystyrene is used as a standard sample, and a weight average molecular weight measured in a N,N-dimethylformamide (DMF) solvent is 342486 Da, a number average molecular weight is 276301 Da, and a molecular weight distribution index is 1.23.

Embodiment 14

[0194] ##STR00183##

[0195] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E4 is synthesized by a method similar with the method disclosed in Tetrahedron Letters, 2012, 53(47), 6383-6387, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0196] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P4 is as follows. The diosmapentalyne monomer M100 (0.08 mmol) and the diacetylene E4 (0.081 mmol) are dissolved in 12 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 1.2 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M100 at room temperature (e.g., 20-25° C.) for 3 hours, a large amount of ethyl ether is then added, a dark-blue solid compound is precipitated and filtered, and the dark-blue solid compound is repeatedly washed with ethyl ether and dried to obtain 204 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P4.

[0197] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P4 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=6.10 (br, 4H, C.sup.10H and C.sup.11H), 5.76 (m, 2H, C.sup.13H), 5.24 (br, 4H, C.sup.9H), 4.36 (br, 4H, C.sup.8H), 4.23 (s, 4H, OCH.sub.2C.sub.7H.sub.15), 2.10 (s, 4H, OCH.sub.2CH.sub.2C.sub.6H.sub.13), 1.71 (s, 4H, OC.sub.2H.sub.4CH.sub.2C.sub.5H.sub.11), 1.37-1.30 (m, 16H, OC.sub.2H.sub.4C.sub.4H.sub.8CH.sub.3), 0.95 (s, 6H, CH.sub.3), 8.31-7.11 ppm (102H, other aromatic protons and C.sup.12H). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.77 (s, CPPh.sub.3), −0.06 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.3 (s, C.sup.1), 217.5 (s, C.sup.7), 172.3 (s, C.sup.5), 169.2 (s, C.sup.6), 168.1 (s, C.sup.4), 159.1 (s, C.sup.3), 76.79 (s, OCH.sub.2C.sub.7H.sub.15), 74.04 (m, C.sup.8), 70.95 (s, C.sup.9), 31.88, 30.64, 29.59, 29.35, 26.78, 22.71, 13.99, 163.4-113.4 ppm (other aromatic carbons).

[0198] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P4 is as follows: polystyrene is used as a standard sample, and a weight average molecular weight measured in a N,N-dimethylformamide (DMF) solvent is 435639 Da, a number average molecular weight is 243582 Da, and a molecular weight distribution index is 1.78.

Embodiment 15

[0199] ##STR00184##

[0200] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E5 is synthesized according to the method reported in Polymer Chemistry, 2014, 5(7), 2301-2308, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0201] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P5 is as follows. The diosmapentalyne monomer M100 (0.085 mmol) and the diacetylene E5 (0.085 mmol) are dissolved in 10 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 1 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M100 at room temperature (e.g., 20-25° C.) for 5 hours, a large amount of ethyl ether is then added, a purple-red solid compound is precipitated and filtered, and the purple-red solid compound is repeatedly washed with ethyl ether and dried to obtain 193 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P5.

[0202] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P5 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=5.90 (br, 4H, C.sup.10H and C.sup.11H), 5.80 (m, 2H, C.sup.14H), 5.60 (m, 2H, C.sup.13H), 5.16 (br, 4H, C.sup.9H), 4.32 (br, 4H, C.sup.8H), 7.88-7.10 ppm (104H, other aromatic protons and C.sup.12H). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.75 (s, CPPh.sub.3), 0.08 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.3 (s, C.sup.1), 218.1 (s, C.sup.7), 172.3 (s, C.sup.5), 169.1 (s, C.sup.6), 168.0 (d, J.sub.P—C=20.47 Hz, C.sup.4), 158.8 (d, J.sub.P—C=13.19 Hz, C.sup.3), 83.53 (end-capper alkyne), 78.19 (end-capper alkyne), 74.29 (m, C.sup.8), 71.04 (s, C.sup.9), 163.4-112.7 ppm (other aromatic carbons).

[0203] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P5 is as follows: polystyrene is used as a standard sample, and a weight average molecular weight measured in a N,N-dimethylformamide (DMF) solvent is 320820 Da, a number average molecular weight is 223498 Da, and a molecular weight distribution index is 1.43.

Embodiment 16

[0204] ##STR00185##

[0205] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E6 (i.e., 3,8-diynyl-1,10-phenanthroline) is purchased from Shanghai Kaiyulin Pharmaceutical Technology Co., Ltd. with a trade name is 640297-84-3, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0206] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P6 is as follows. The diosmapentalyne monomer M100 (0.089 mmol) and the diacetylene E6 (0.090 mmol) are dissolved in 10 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 1 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M100 at room temperature (e.g., 20-25° C.) for 1 hour, a large amount of ethyl ether is then added, a dark-blue solid compound is precipitated and filtered, and the dark-blue solid compound is repeatedly washed with ethyl ether and dried to obtain 181 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P6.

[0207] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P6 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=6.36 (m, 2H, C.sup.13H), 5.90 (br, 4H, C.sup.10H and C.sup.11H), 5.36 (br, 4H, C.sup.9H), 4.54 (br, 4H, C.sup.8H), 9.23-7.28 ppm (102H, other aromatic protons and C.sup.12H). .sup.31P NMR (202.5 MHz, DMF-D7): δ=4.79 (s, CPPh.sub.3), −0.87 ppm (s, OsPPh.sub.3).

[0208] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P6 is as follows: a weight average molecular weight is 16573 Da, a number average molecular weight is 15493 Da, and a molecular weight distribution index is 1.07.

Embodiment 17

[0209] ##STR00186##

[0210] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E7 (i.e., [1,2-diphenyl-1,2-bis(4-ynyl) Phenyl] ethylene) is purchased from Beijing Huaweiruike Chemical Co., Ltd. with a trade name is 1240785-42-5, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0211] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P7 is as follows. The diosmapentalyne monomer M100 (0.088 mmol) and the diacetylene E7 (0.090 mmol) are dissolved in 10 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 1 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M100 at room temperature (e.g., 20-25° C.) for 5 hours, a large amount of ethyl ether is then added, a blue-black solid compound is precipitated and filtered, and the blue-black solid compound is repeatedly washed with ethyl ether and dried to obtain 219 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P7.

[0212] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P7 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=5.77 (br, 6H, C.sup.13H, C.sup.10H and C.sup.11H), 5.09 (br, 4H, C.sup.9H), 4.25 (br, 4H, C.sup.8H), 8.32-6.94 ppm (114H, other aromatic protons and C.sup.12H). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.79 (s, CPPh.sub.3), 0.22 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.3 (s, C.sup.1), 218.5 (s, C.sup.7), 172.4 (s, C.sup.5), 169.0 (s, C.sup.6), 167.8 (d, J.sub.P—C=20.10 Hz, C.sup.4), 158.6 (d, J.sub.P—C=12.84 Hz, C.sup.3), 83.43 (end-capper alkyne), 77.77 (end-capper alkyne), 73.74 (m, C.sup.8), 70.79 (s, C.sup.9), 144.8-119.4 ppm (other aromatic carbons).

[0213] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P7 is as follows: a weight average molecular weight is 17260 Da, a number average molecular weight is 11217 Da, and a molecular weight distribution index is 1.54.

Embodiment 18

[0214] ##STR00187##

[0215] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E8 is synthesized according to the method reported in Journal of Physical Chemistry B, 2007, 111(37), 10871-10880, and DCE used in the above-mentioned formula is 1,2-dichloroethane of China National Pharmaceutical Group Co., Ltd. (Sinopharm).

[0216] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P8 is as follows. The diosmapentalyne monomer M100 (0.055 mmol) and the diacetylene E8 (0.056 mmol) are dissolved in 8 mL of the 1,2-dichloroethane by a magnetic stirrer under a nitrogen atmosphere, and 0.3 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M100 at room temperature (e.g., 20-25° C.) for 5 hours, a large amount of ethyl ether is then added, a dark-green solid compound is precipitated and filtered, and the dark-green solid compound is repeatedly washed with ethyl ether and dried to obtain 118 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P8 shown in FIG. 4.

[0217] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P8 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=5.99 (br, 4H, C.sup.10H and C.sup.11H), 5.67 (br, 2H, C.sup.13H), 5.08 (br, 4H, C.sup.9H), 4.35 (br, 4H, C.sup.8H), 8.00-6.90 ppm (100H, other aromatic protons and C.sup.12H). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.71 (s, CPPh.sub.3), −0.21 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.1 (s, C.sup.1), 190.2 (s, C.sup.7), 171.9 (s, C.sup.5), 169.0 (s, C.sup.6), 167.8 (s, C.sup.4), 158.6 (s, C.sup.3), 74.20 (m, C.sup.8), 70.91 (s, C.sup.9), 145.4-111.4 ppm (other aromatic carbons).

[0218] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P8 is as follows: a weight average molecular weight is 16123 Da, a number average molecular weight is 15577 Da, and a molecular weight distribution index is 1.04.

Embodiment 19

[0219] ##STR00188##

[0220] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E5 is synthesized according to the method reported in Polymer Chemistry, 2014, 5(7), 2301-2308, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0221] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P9 is as follows. The diosmapentalyne monomer M200 (0.091 mmol) and the diacetylene E5 (0.092 mmol) are dissolved in 10 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 1 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M200 at room temperature (e.g., 20-25° C.) for 5 hours, a large amount of ethyl ether is then added, a purple-red solid compound is precipitated and filtered, and the purple-red solid compound is repeatedly washed with ethyl ether and dried to obtain 209 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P9 shown in FIG. 4.

[0222] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P9 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=5.96 (br, 4H, C.sup.10H), 5.89 (s, 1H, C.sup.13H), 5.77 (d, J=16.25 Hz, 2H, C.sup.12H), 5.59 (s, 1H, C.sup.14H), 5.12 (br, 4H, C.sup.9H), 3.68 (br, 4H, C.sup.8H), 7.96-7.07 ppm (108H, other aromatic protons and C.sup.11H). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.41 (s, CPPh.sub.3), −0.81 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.0 (s, C.sup.1), 217.8 (s, C.sup.7), 173.3 (s, C.sup.5), 168.9 (s, C.sup.6), 165.3 (s, C.sup.4), 162.1 (s, C.sup.3), 73.17 (s, C.sup.8), 70.73 (s, C.sup.9), 142.4-112.6 ppm (other aromatic carbons).

[0223] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P9 is as follows: diffusion coefficients D of the main chain comprising the osmapentalyne-containing conjugated polymer P9 and a model compound are tested using a Nuclear Magnetic Resonance (NMR) diffusion order spectroscopy (DOSY) technology (Macromolecules, 2012, 45, 9595-9603) to speculate an average molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P9 to be 41892.

Embodiment 20

[0224] ##STR00189##

[0225] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E5 is synthesized according to the method reported in Polymer Chemistry, 2014, 5(7), 2301-2308, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0226] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P10 is as follows. The diosmapentalyne monomer M300 (0.10 mmol) and the diacetylene E5 (0.101 mmol) are dissolved in 10 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 1 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M300 at room temperature (e.g., 20-25° C.) for 5 hours, a large amount of ethyl ether is then added, a dark-blue solid compound is precipitated and filtered, and the dark-blue solid compound is repeatedly washed with ethyl ether and dried to obtain 225 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P10.

[0227] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P10 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=6.23 (d, J=16.11 Hz, 4H, C.sup.11H and C.sup.12H), 5.89 (s, 1H, C.sup.15H), 5.67 (br, 2H, C.sup.14H), 5.59 (s, 1H, C.sup.16H), 3.02 (br, 4H, C.sup.10H), 2.09 (br, 4H, C.sup.9H), 1.30 (br, 4H, C.sup.8H), 7.96-6.98 ppm (104H, other aromatic protons and C.sup.13). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.45 (s, CPPh.sub.3), 1.08 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.4 (s, C.sup.1), 220.4 (s, C.sup.7), 179.3 (s, C.sup.5), 174.2 (s, C.sup.6), 170.7 (s, C.sup.4), 157.6 (s, C.sup.3), 37.12 (s, C.sup.8), 32.54 (s, C.sup.9), 30.34 (s, C.sup.10), 163.3-112.6 ppm (other aromatic carbons).

[0228] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P10 is as follows: diffusion coefficients D of the main chain comprising the osmapentalyne-containing conjugated polymer P10 and a model compound are tested using a Nuclear Magnetic Resonance (NMR) diffusion order spectroscopy (DOSY) (Macromolecules, 2012, 45, 9595-9603) to speculate an average molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P10 to be 21322.

Embodiment 21

[0229] ##STR00190##

[0230] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E11 is purchased from Beijing Huaweiruike Chemical Co., Ltd. with a product number of HWG58301-5g, and DCM used in the above-mentioned formula is 1,2-Dichloroethane.

[0231] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P11 is as follows. The diosmapentalyne monomer M100 (0.08 mmol) and the diacetylene E11 (0.08 mmol) are dissolved in 10 mL of the 1,2-dichloroethane by a magnetic stirrer under a nitrogen atmosphere, and 0.4 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M100 at room temperature (e.g., 20-25° C.) for 2 hours, a large amount of ethyl ether is then added, a dark-blue solid compound is precipitated and filtered, and the dark-blue solid compound is repeatedly washed with ethyl ether and dried to obtain 192 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P11.

[0232] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P11 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=6.10 (m, 4H, C.sup.10H and C.sup.11H), 5.90 (s, 2H, C.sup.12H), 5.50 (s, 2H, C.sup.13H), 5.12 (s, 4H, C.sup.9H), 4.37 (s, 4H, C.sup.8H), 4.23 (m, 4H, OCH.sub.2C.sub.7H.sub.15), 2.05 (m, 4H, OCH.sub.2CH.sub.2C.sub.6H.sub.13), 1.53-1.30 (m, 20H, OC.sub.2H.sub.4C.sub.5H.sub.10CH.sub.3), 0.92 (m, 6H, OC.sub.7H.sub.14CH.sub.3), 8.62-6.88 ppm (98H, other aromatic protons). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.55 (s, CPPh.sub.3), −0.20 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.3 (s, C.sup.1), 216.7 (s, C.sup.7), 171.8 (s, C.sup.5), 168.9 (s, C.sup.6), 167.7 (s, C.sup.4), 158.2 (s, C.sup.3), 74.55, 73.87 (s, C.sup.8), 70.94 (s, C.sup.9), 31.78, 30.40, 29.55, 29.36, 26.03, 22.68, 13.99, 152.0-112.3 ppm (other aromatic carbons).

[0233] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P11 is as follows: a weight average molecular weight is 29122 Da, a number average molecular weight is 14433 Da, and a molecular weight distribution index is 2.01.

Embodiment 22

[0234] ##STR00191##

[0235] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E12 is synthesized by a method similar with the method disclosed in Inorganic Chemistry, 2009, 48(14), 6534-6547, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0236] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P12 is as follows. The diosmapentalyne monomer M100 (0.20 mmol) and the diacetylene E12 (0.201 mmol) are dissolved in 20 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 2 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M100 at room temperature (e.g., 20-25° C.) for 5 hours, a large amount of ethyl ether is then added, a dark-blue solid compound is precipitated and filtered, and the dark-blue solid compound is repeatedly washed with ethyl ether and dried to obtain 490 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P12.

[0237] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P12 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=5.84 (br, 6H, C.sup.10H, C.sup.11H, and C.sup.13H), 5.12 (br, 4H, C.sup.9H), 4.29 (br, 4H, C.sup.8H), 4.10 (s, 4H, OCH.sub.2CH.sub.2CH.sub.2), 1.08 (s, 8H, OCH.sub.2CH.sub.2CH.sub.2), 0.92-0.89 (br, 6H, CH.sub.3), 7.88-7.09 ppm (106H, other aromatic protons and C.sup.12H). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.83 (s, CPPh.sub.3), −0.03 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.1 (s, C.sup.1), 217.1 (s, C.sup.7), 172.3 (s, C.sup.5), 169.3 (s, C.sup.6), 168.1 (s, C.sup.4), 159.5 (s, C.sup.3), 95.64 (s, C.sup.15), 94.23 (end-capper alkyne), 88.08 (s, C.sup.14), 88.07 (end-capper alkyne), 83.05 (end-capper alkyne), 79.06 (end-capper alkyne), 73.70 (m, C.sup.8), 70.86 (s, C.sup.9), 69.35, 31.38, 19.32, 13.73, 163.4-114.1 ppm (other aromatic carbons).

[0238] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P12 is as follows: diffusion coefficients D of the main chain comprising the osmapentalyne-containing conjugated polymer P12 and a model compound are tested using a Nuclear Magnetic Resonance (NMR) diffusion order spectroscopy (DOSY) (Macromolecules, 2012, 45, 9595-9603) to speculate an average molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P12 to be 83497.

Embodiment 23

[0239] ##STR00192##

[0240] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E13 is synthesized by a method similar with the method disclosed in Inorganic Chemistry, 2009, 48(14), 6534-6547, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0241] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P13 is as follows. The diosmapentalyne monomer M100 (0.15 mmol) and the diacetylene E13 (0.151 mmol) are dissolved in 15 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 1.5 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M100 at room temperature (e.g., 20-25° C.) for 5 hours, a large amount of ethyl ether is then added, a dark-blue solid compound is precipitated and filtered, and the dark-blue solid compound is repeatedly washed with ethyl ether and dried to obtain 386 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P13.

[0242] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P13 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=5.83 (br, 6H, C.sup.10H, C.sup.11H, and C.sup.13H), 5.12 (br, 4H, C.sup.9H), 4.31 (br, 4H, C.sup.8H), 4.09 (s, 4H, OCH.sub.2C.sub.7H.sub.15), 1.33-1.30 (m, 24H, OCH.sub.2C.sub.5H.sub.12CH.sub.3), 0.91-0.90 (br, 6H, CH.sub.3), 7.88-7.09 ppm (106H, other aromatic protons and C.sup.12H). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.82 (s, CPPh.sub.3), −0.04 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.2 (s, C.sup.1), 217.0 (s, C.sup.7), 172.2 (s, C.sup.5), 169.2 (s, C.sup.6), 168.1 (s, C.sup.4), 159.5 (s, C.sup.3), 95.66 (s, C.sup.15), 94.25 (end-capper alkyne), 88.10 (s, C.sup.14), 88.09 (end-capper alkyne), 83.06 (end-capper alkyne), 79.07 (end-capper alkyne), 74.36 (m, C.sup.8), 70.92 (s, C.sup.9), 69.63, 31.84, 29.35, 26.09, 22.70, 13.94, 153.6-113.7 ppm (other aromatic carbons).

[0243] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P13 is as follows: diffusion coefficients D of the main chain comprising the osmapentalyne-containing conjugated polymer P13 and a model compound are tested using a Nuclear Magnetic Resonance (NMR) diffusion order spectroscopy (DOSY) (Macromolecules, 2012, 45, 9595-9603) to speculate an average molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P13 to be 40014.

Embodiment 24

[0244] ##STR00193##

[0245] In the above-mentioned formula, [Os] is OsCl(PPh.sub.3).sub.2, wherein HCl.Et.sub.2O is hydrochloric acid in ethyl ether (which is purchased from Saen Chemical Technology (Shanghai) Co., Ltd., a trade name is A01W8101821000), diacetylene E14 is synthesized by a method similar with the method disclosed in Inorganic Chemistry, 2009, 48(14), 6534-6547, and DCM used in the above-mentioned formula is a redistilled solvent of dichloromethane.

[0246] A method for preparing a main chain comprising an osmapentalyne-containing conjugated polymer P14 is as follows. The diosmapentalyne monomer M100 (0.33 mmol) and the diacetylene E14 (0.331 mmol) are dissolved in 30 mL of the redistilled solvent of the dichloromethane by a magnetic stirrer under a nitrogen atmosphere, and 3 mL of 2 mol/L of the hydrochloric acid in the ethyl ether is quickly added and is reacted with the diosmapentalyne monomer M100 at room temperature (e.g., 20-25° C.) for 5 hours, a large amount of ethyl ether is then added, a dark-blue solid compound is precipitated and filtered, and the dark-blue solid compound is repeatedly washed with ethyl ether and hexane and dried to obtain 849 mg of the main chain comprising the osmapentalyne-containing conjugated polymer P14 shown in FIG. 5.

[0247] A data acknowledgement of a structure of the main chain comprising the osmapentalyne-containing conjugated polymer P14 is as follows: .sup.1H NMR (500.2 MHz, CD.sub.2Cl.sub.2): δ=5.82 (br, 6H, C.sup.10H, C.sup.11H, and C.sup.13H), 5.14 (br, 4H, C.sup.9H), 4.30 (br, 4H, C.sup.8H), 4.09 (s, 4H, OCH.sub.2C.sub.11H.sub.23), 1.45-1.24 (m, 40H, OCH.sub.2C.sub.5H.sub.12CH.sub.3), 0.90 (s, 6H, CH.sub.3), 7.88-7.09 ppm (106H, other aromatic protons and C.sup.12H). .sup.31P NMR (202.5 MHz, CD.sub.2Cl.sub.2): δ=4.84 (s, CPPh.sub.3), −0.04 ppm (s, OsPPh.sub.3). .sup.13C NMR (150.9 MHz, CD.sub.2Cl.sub.2): δ=316.1 (s, C.sup.1), 217.1 (s, C.sup.7), 172.3 (s, C.sup.5), 169.3 (s, C.sup.6), 168.1 (s, C.sup.4), 159.5 (s, C.sup.3), 95.62 (s, C.sup.15), 94.25 (end-capper alkyne), 88.08 (s, C.sup.14), 88.07 (end-capper alkyne), 83.05 (end-capper alkyne), 79.03 (end-capper alkyne), 74.33 (m, C.sup.8), 70.95 (s, C.sup.9), 69.62 (s, OCH.sub.2C.sub.11H.sub.23), 31.92, 29.66, 29.36, 26.03, 22.70, 13.93, 163.4-114.1 ppm (other aromatic carbons).

[0248] A characterization data of a molecular weight of the main chain comprising the osmapentalyne-containing conjugated polymer P14 is as follows: polystyrene is used as a standard sample, and a weight average molecular weight measured in a N,N-dimethylformamide (DMF) solvent is 462172 Da, a number average molecular weight is 380070 Da, and a molecular weight distribution index is 1.22.

[0249] The aforementioned embodiments are merely some embodiments of the present disclosure, and the scope of the disclosure is not limited thereto. Thus, it is intended that the present disclosure cover any modifications and variations of the presently presented embodiments provided they are made without departing from the appended claims and the specification of the present disclosure.