STRONGLY POLARIZED MOLECULE, AND SINGLE MOLECULE FIELD EFFECT TRANSISTOR PREPARED THEREFROM

Abstract

The application relates to a strongly-polarized molecule of the following general formula: wherein A denotes a group having a polarizability greater than 2 C.Math.m.sup.2/V; R.sub.1 and R.sub.2 are respectively hydrogen, halogen, a hydroxyl group, an amino group, a cyano group, a nitro group, a carboxyl group, a C.sub.1-12 alkyl group, a C.sub.1-12 alkoxy group, a halogenated C.sub.1-12 alkyl group, a halogenated C.sub.1-12 alkoxy group, a hydroxyl C.sub.1-12 alkyl group, a hydroxyl C.sub.1-12 alkoxy group, or a C.sub.1-12 alkyl amino group; x.sub.1 and x.sub.2 denote 0 or an integer no less than 1, respectively; and y.sub.1 and y.sub.2 denote 0 or an integer no less than 1, respectively. The application further relates to a strongly-polarized molecule-graphene molecule heterojunction, and a single molecule field effect transistor comprising a substrate, a gate, a dielectric layer and the strongly-polarized molecule-graphene molecule heterojunction; and the dielectric layer is located between the gate and the strongly-polarized molecule-graphene molecule heterojuction. The single molecule field effect transistor provided by the application can realize highly-efficient gate modulation.

##STR00001##

Claims

1. An strongly-polarized molecule represented by general formula (I): ##STR00030## wherein, A is a group having a polarizability greater than 2 C.Math.m.sup.2/V; R.sub.1 and R.sub.2 are respectively any one of hydrogen, halogen, hydroxyl, amino, cyano, nitro, carboxyl, C.sub.1-12 alkyl, C.sub.1-12 alkoxy, halogenated C.sub.1-12 alkyl, halogenated C.sub.1-12 alkoxy, hydroxyl C.sub.1-12 alkyl, hydroxyl C.sub.1-12 alkoxy, and C.sub.1-12 alkyl amino; x.sub.1 and x.sub.2 are 0 or a positive integer respectively; y.sub.1 and y.sub.2 are 0 or a positive integer respectively.

2. The strongly-polarized molecule according to claim 1, wherein A is: ##STR00031## ##STR00032## R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and Ru are respectively any one of hydrogen, halogen, hydroxyl, amino, cyano, nitro, carboxyl, C.sub.1-12 alkyl, C.sub.1-12 alkoxy, halogenated C.sub.1-12 alkyl, halogenated C.sub.1-12 alkoxy, hydroxyl C.sub.1-12 alkyl, hydroxyl C.sub.1-12 alkoxy, and C.sub.1-12 alkyl amino; M.sub.1, M.sub.2, M.sub.3, M.sub.4, M.sub.5 and M.sub.6 are respectively a central atom or central ion of the complex; n.sub.1, n.sub.2, n.sub.3, n.sub.4, n.sub.5, n.sub.6, n.sub.7, n.sub.8, n.sub.9, n.sub.10, n.sub.11, n.sub.12, n.sub.13, n.sub.14, n.sub.15, n.sub.16 and n.sub.17 are respectively a positive integer.

3. The strongly-polarized molecule according to claim 1, having any one of the following general formulae: ##STR00033## ##STR00034## ##STR00035## wherein, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, M.sub.1, M.sub.2, M.sub.3, M.sub.4, M.sub.5, M.sub.6, n.sub.2, n.sub.6, n.sub.7, n.sub.8, n.sub.9, n.sub.10, n.sub.11, n.sub.12, n.sub.13, n.sub.14, n.sub.15, n.sub.16, n.sub.17, x.sub.1, x.sub.2, y.sub.1, and y.sub.2 are as defined in claim 1.

4. The strongly-polarized molecule according to claim 1, having any one of the following structural formulae: ##STR00036## ##STR00037## ##STR00038##

5. A strongly-polarized molecule-graphene molecule heterojunction, wherein the molecule heterojunction comprises the strongly-polarized molecule according to claim 1 bridging between layers of two-dimensional single-layer graphene with a nanogap via amide covalent bonds.

6. A single molecule field effect transistor, comprising a substrate, a gate, a dielectric layer, and the strongly-polarized molecule-graphene molecule heterojunction according to claim 5, wherein the dielectric layer is located between the gate and the strongly-polarized molecule-graphene molecular heterojunction.

7. The single molecule field effect transistor according to claim 6, wherein the material of the gate is one of graphene or metal aluminum.

8. The single molecule field effect transistor according claim 6, wherein the material of the dielectric layer is one of hafnium oxide, zirconium oxide, titanium oxide, and aluminum oxide, or any combinations thereof.

9. The single molecule field effect transistor according to claim 6, wherein: the dielectric layer is a hafnium oxide layer, and the gate is a graphene layer; or the dielectric layer is a zirconium oxide layer, and the gate is a graphene layer; or the dielectric layer is a titanium oxide layer, and the gate is a graphene layer; or the dielectric layer is an aluminium oxide layer, and the gate is a metal aluminum layer; or the dielectric layer is a composite layer of aluminium oxide and hafnium oxide, and the gate is a metal aluminum layer.

10. The single molecule field effect transistor according to claim 6, wherein the substrate is a silicon wafer having a silicon oxide layer.

11. The single molecule field effect transistor according to claim 6, wherein the thickness of the dielectric layer is 3-10 nm.

12. The single molecule field effect transistor according to claim 6, wherein the gate is located on the substrate, the dielectric layer is located on the gate, and the strongly-polarized molecule-graphene molecule heterojunction is located on the dielectric layer; or the strongly-polarized molecule-graphene molecule heterojunction is located on the substrate, the dielectric layer is located on the strongly-polarized molecule-graphene molecule heterojunction, and the gate is located on the dielectric layer.

13. A molecular switch comprising the single molecule field effect transistor according to claim 6.

14. A semiconductor chip comprising the single molecule field effect transistor according to claim 6.

15. The strongly-polarized molecule according to claim 1, wherein 0x.sub.13; 0x.sub.23.

16. The strongly-polarized molecule according to claim 1, wherein 0y.sub.12, 0y.sub.22.

17. The strongly-polarized molecule according to claim 2, wherein M.sub.1, M.sub.2, M.sub.3, M.sub.4, M.sub.5 and M.sub.6 are respectively selected from the group consisting of Ru, Fe, Zn, Mn, Co, Ni and cation thereof.

18. The strongly-polarized molecule according to claim 2, wherein n.sub.1, n.sub.2, n.sub.3, n.sub.4, n.sub.5, n.sub.6, m, n.sub.8, n.sub.9, n.sub.10, n.sub.11, n.sub.12, n.sub.13, n.sub.14, n.sub.15, n.sub.16 and n.sub.17 are smaller than or equal to 3.

19. The strongly-polarized molecule-graphene molecule heterojunction according to claim 5, wherein the two-dimensional single-layer graphene with a nanogap is a two-dimensional single-layer graphene with a nanogap array.

20. The single molecule field effect transistor according to claim 10, wherein the thickness of the silicon oxide layer is 200-400 nm.

Description

DESCRIPTION OF THE DRAWINGS

[0065] In order to more clearly illustrate the examples of the present application and the embodiments of the prior art, the following description of the embodiments and the drawings of the prior art will be briefly described. It is obvious to those skilled in the art that the drawings in the following description are only some examples of the application, and may be used to obtain other figures from these figures without any inventive efforts.

[0066] FIG. 1 is a schematic diagram of the structure of the single molecule field effect transistor with a bottom gate structure.

[0067] FIG. 2 is a schematic diagram of the structure of the single molecule field effect transistor with a top gate structure.

[0068] FIG. 3 is an I-V characteristic curve of the compound 1 based single molecule field effect transistor prepared in Example 1.

[0069] FIG. 4 is an I-V characteristic curve of the compound 2 based single molecule field effect transistor prepared in Example 2 within a gate voltage range of 2 V to +2 V.

[0070] FIG. 5 is an I-V characteristic curve of the compound 3 based single molecule field effect transistor prepared in Example 3 within a gate voltage range of 2 V to +2 V.

[0071] FIG. 6 is an I-V characteristic curve of the compound 4 based single molecule field effect transistor prepared in Example 4 within a gate voltage range of 2 V to +2 V.

[0072] FIG. 7 is an I-V characteristic curve of the compound 5 based single molecule field effect transistor prepared in Example 5 within a gate voltage range of 2 V to +2 V.

[0073] FIG. 8 is an I-V characteristic curve of the compound 6 based single molecule field effect transistor prepared in Example 6 within a gate voltage range of 2 V to +2 V.

[0074] FIG. 9 is an I-V characteristic curve of the compound 7 based single molecule field effect transistor prepared in Example 7 within a gate voltage range of 2 V to +2 V.

DETAILED DESCRIPTION OF THE INVENTION

[0075] The technical solutions in the embodiments of the present application are clearly and completely described in the following with reference to the drawings in the examples of the present application. It is obvious that the described examples are only a part of the examples of the present application, but not all of them. All other examples obtained by those skill in the art based on the examples of the present application without making inventive efforts are within the scope of the present application.

[0076] The experimental methods described in the following examples are conventional methods unless otherwise specified. The reagents and materials, unless otherwise specified, are commercially available.

Preparation Example of Single Molecule Field Effect Transistor

Example 1: Preparation of Compound 1 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 1

[0077] The synthetic route is as follows:

##STR00009## ##STR00010##

[0078] Compound A was synthesized according to the method described in the literature (J. Am. Chem. Soc., 2010, 132 (44), pp 15547-15549).

[0079] Compound A (857 mg, 1.23 mmol), N-Boc-4-aminophenylboronic acid pinacol ester (865 mg, 2.71 mmol), bis(dibenzalacetone) palladium (22.6 mg, 24.6 mol), tri(o-tolyl)phosphine (30.1 mg, 98.6 mop, and anhydrous potassium carbonate (1.60 g, 11.6 mmol) were added to a 100 mL Schlenk bottle in sequence. After adding 2 drops of aliquat 336 (methyl trioctyl ammonium chloride), 24 mL of toluene and 6 mL of distilled water were injected. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 24 h. After cooling, the reaction mixture was poured into water (50 mL) and extracted with dichloromethane (330 mL). After the organic phases were combined and dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound B as a purple solid. .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.87 (d, =8.5 Hz, 2.11), 7.65 (ddd, 0.1=8.7, 1.3, 0.4 Hz, 4H), 739 (m, 614), 4.10 (d, 7.0 Hz, 4H), 1.64 (m, 2H), 1.45 (s, 18H), 1.15-1.38 (m, 14H), 0.76-0.91 (m, 16H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 1.7183, 153.93, 148.85, 145.64, 138.76, 133.63, 127.67, 127.38, 123.40, 121.45, 119.57, 100.02, 80.43, 46.33, 38.65, 37.60, 32.11, 30.79, 79.64, 28.61, 28.16, 75.09, 23.56, 22.79, 14.09, 14.06, 11.51. HRMS (TOF-ESI) (m/z): C.sub.53H.sub.68N.sub.4O.sub.6S.sub.2 calculated: 921.47 [M+H.sup.+]; found: 921.49.

[0080] Trifluoroacetic acid (1.0 mL, 0.34 g, 3.73 mmol) was added dropwise to compound B (0.120 g, 0.13 mmol) in dichloromethane (10 mL). After stirring for 2 hours at room temperature, the reaction mixture was added dropwise to saturated aqueous sodium bicarbonate solution (20 mL), and extracted with dichloromethane (50 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (30 mL) and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo to obtain interested compound 1 as a dark purple solid.

[0081] .sup.1H NMR (400 MHz, CDCl.sub.3, 2515 K): 7.80 (d, J=8.5 Hz, 2H), 7.35 (ddd, J=8.2, 1.6, 0.4 Hz, 4H), 7.26 (d, J=8.5 Hz, 2H), 7.02 (ddd, J=8.7, 1.2, 0.4 Hz, 4H), 4.12 (d, J=7.0 Hz, 4H), 1.64 (m, 2H), 1.15-1.38 (m, 14H), 0.76-1.91 (m, 16H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 172.83, 150.10, 148.85, 145.64, 133.63, 128.09, 127.67, 122.80, 121.45, 144.80, 100.02, 46.33, 38.65, 32.60, 32.11, 30.79, 29.64, 28.61, 25.09, 23.56, 22.79, 14.09, 14.06, 11.51, HRMS (TOF-ESI.sup.+) (m/z):

[0082] C.sub.43H.sub.52N.sub.4O.sub.2S.sub.2 calculated: 721.36 [M+H.sup.+]; found: 721.35.

(2) Preparation of Compound 1 Based Single Molecule Field Effect Transistor

[0083] Graphene was used as the gate electrode, and hafnium oxide with a thickness of 5 nm was used as the dielectric layer to construct a field effect transistor with a bottom gate structure.

[0084] First, the single-layer graphene grown by chemical vapor deposition was transferred onto a silicon wafer having a oxide layer of 300 nm, as the bottom gate.

[0085] A hafnium oxide layer with a thickness of 5 nm was deposited on the bottom gate by the sol-gel method.

[0086] A two-dimensional single-layer graphene with a nanogap was constructed on the dielectric layer to obtain a molecule device to be assembled.

[0087] A strongly-polarized molecule-graphene molecule heterojunction was constructed on the molecule device to be assembled to obtain a single molecule field effect transistor device. The specific process is as follows.

[0088] First, the compound of formula 1 and the carbodiimide dehydrator-activator 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloric acid (EDCI) were dissolved in pyridine. The concentrations were 10.sup.4 mol/L and 310.sup.3 mol/L, respectively. Then, the molecule device to be assembled was added into the above solution, and reacted for 48 h in argon atmosphere in dark. After that, the device was taken out of the solution, washed with acetone and ultrapure water three times, respectively, and dried with a nitrogen stream to obtain the compound 1 based single molecule field effect transistor.

[0089] It should be noted that the specific methods, conditions, parameters, and the like in the preparation process of the molecule device to be assembled can be implemented according to the methods in the relevant documents previously described herein, which will not be repeated in this application.

Example 2: Preparation of Compound 2 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 2

[0090] The synthetic route is as follows:

##STR00011## ##STR00012##

[0091] Compound A was synthesized according to the method of Example 1.

[0092] Compound A (697 mg, 1.00 mmol), 4-(N-Boc-aminomethyl)phenylboronic acid pinacol ester (734 mg, 2.20 mmol), bis(dibenzalacetone) palladium (18.4 mg, 20 mop, tri(o-tolyl)phosphine (24.5 mg, 80.2 mop, and anhydrous potassium carbonate (1.30 g, 9.43 mmol) were added to a 100 mL Schlenk bottle in sequence. After adding 2 drops of aliquat 336, 24 mL of toluene and 6 mL of distilled water were injected. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 24 h. After cooling, the reaction mixture was poured into water (50 mL) and extracted with dichloromethane (330 mL). After the organic phases were combined and dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound C as a purple solid.

[0093] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.70 (d, J=8.6 Hz, 2H). 7.60-7.67 (m, 4H), 7.40 (ddd, J=8.5, 1.5, 0.5 Hz 6H), 4.32 (s, 4H), 4.12 (d, J=7.0 HZ, 4H), 1.54-1.76 (m 2H), 1.44 (s, 18H), 1.15-1.38 (m, 14H), 0.76-0.91 (m, 16H). .sup.13C NMR (100 MHz, CDCl.sub.7, 298 K): 172.83, 156.0.3, 148.85, 145.64, 143.21, 133.63, 133.12, 128.11, 127.67, 126.29, 121.45, 100.02, 79.66, 46.33, 43.70, 38.65, 32.60, 32.11, 30.79, 29.64, 28.61, 28.30, 25.09, 23.56, 22.79, 14.09, 14.06, 11.51. HRMS (TOF-ESI.sup.+) (m/z): C.sub.55H.sub.72O.sub.6S.sub.2 calculated: 94). 50 [M+H.sup.+]; found: 949.50.

[0094] The located reaction was carried out according to the method of Example 1, except that compound B was relocated with compound C (0.120 g, 0.13 mmol), to obtain the interested compound 2 as a dark purple solid.

[0095] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.70 (d, J=8.6 Hz, 2H), 7.63 (dd, J=6.5, 1.3 Hz, 4H), 7.38 (ddd, J=6.5, 1.3, 0.5 Hz, 6H), 4.10 (d, J=7.0 Hz, 4H), 3.67 (s, 4H), 1.54-4.76 (in, 2H), 1.15-1.38 (m, 14H), 0.76-0.91 (m, 16H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 172.83, 148.85, 145.64, 141.15, 133.63, 133.34, 128.28, 127.67, 126.74, 121.45, 100.02, 46.33, 45.58, 38.65, 32.60, 32.11, 30.79, 29.64, 28.61, 25.09, 23.56, 22.79, 14.09, 14.06, 11.51. HRMS (TOF-ESI.sup.+) (m/z): C.sub.45H.sub.56N.sub.4O.sub.2S.sub.2 calculated: 749.39 [M+H.sup.+]; found: 749.35.

(2) Preparation of Compound 2 Based Single Molecule Field Effect Transistor

[0096] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 2 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 2 was used to replace compound 1.

Example 3: Preparation of Compound 3 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 3

[0097] The synthetic route is as follows:

##STR00013## ##STR00014##

[0098] Compound A was synthesized according to the method of Example 1.

[0099] Compound A (843 mg, 1.21 mmol), 4-(N-Boc-aminomethyl)phenylboronic acid pinacol ester (924 mg, 2.66 mmol), bis(dibenzalacetone)palladium (22.3 mg, 24 mop, tri(o-tolyl)phosphine (29.6 mg, 97.0 mop, and anhydrous potassium carbonate (1.57 g, 11.41 mmol) were added to a 100 mL Schlenk bottle in sequence. After adding 2 drops of aliquat 336, 24 mL of toluene and 6 mL of distilled water were injected. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 24 h. After cooling, the reaction mixture was poured into water (50 mL) and extracted with dichloromethane (330 mL). After the organic phases were and combined and dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound D as a purple solid.

[0100] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.72 (d, J=8.6 Hz, 2H), 7.64 (ddd, J=8.5, 1.5, 0.5 Hz, 4H), 7.39 (d, J=8.6 Hz, 2H), 7.19 (ddd, J=8.2, 1.5, 0.5 Hz, 4H), 4.13 (d, J=7.0 Hz, 4H), 3.50 (t, J=5.3 Hz, 4H), 2.55 (t, J=5.3 Hz, 4H), 1.54-1.76 (m, 2H), 1.43 (s, 18H), 1.15-1.38 (m, 14H), 0.76-0.91 (m, 16H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 172.83, 156.24, 148.85, 145.64, 136.73, 133.63, 132.41, 128.18, 127.67, 126.64, 121.45, 100.02, 79.52, 46.33, 42.33, 38.65, 35.31, 32.60, 32.11, 30.79, 29.64, 28.61, 28.30, 25.09, 23.56, 22.79, 14.09, 14.06, 11.51. HRMS (TOF-ESI.sup.+) (m/z): C.sub.57H.sub.76N.sub.4O.sub.6S.sub.2 calculated: 977.53 [M+H.sup.+]; found: 977.50.

[0101] The located reaction was carried out according to the method of Example 1, except that compound B was relocated with compound D (0.127 g, 0.13 mmol), to obtain the interested compound 3 as a dark purple solid.

[0102] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.72 (d, J=8.6 Hz, 2H), 7.63 (ddd, J=8.5, 1.5, 0.5 Hz, 4H), 7.38 (d, J=8.6 Hz, 2H), 7.17 (ddd, J=8.1, 1.5, 0.5 Hz, 4H), 4.10 (d, J=7.0 Hz, 4H), 2.76 (t, J=6.6 Hz, 4H), 2.49 (t, J=6.6 Hz, 4H), 1.54-1.76 (m, 211), 1.15-1.38 (m, 14H), 0.76-0.91 (m, 16H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 172.83, 148.85, 145.64, 136.83, 133.63, 132.36, 127.92, 127.67, 126.58, 121.45, 100.02, 46.33, 42.84, 38.87, 38.65, 32.60, 32.11, 30.79, 29.64, 28.61, 25.09, 23.56, 22.79, 14.09, 14.06, 11.51. HRMS (TOF-ESI.sup.+) (m/z): C.sub.47H.sub.60N.sub.4O.sub.2S.sub.2 calculated: 777.42 [M+H.sup.+]; found. 777.42.

(2) Preparation of Compound 3 Based Single Molecule Field Effect Transistor

[0103] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 3 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 3 was used to replace compound 1.

Example 4: Preparation of Compound 4 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 4

[0104] The synthetic route was as follows.

##STR00015## ##STR00016##

[0105] Dichloromethane (15 mL), p-bromoamphetamine (1.293 g, 6.04 mmol) and triethylamine (944 mg, 1.3 mL, 9.33 mmol) were added into a 50 mL reaction flask under the protection of argon, and the reaction flask was located in an ice-water bath. Di-tert-butyl dicarbonate (1.61 g, 1.7 mL, 7.40 mmol) was added dropwise with stirring, allowed to warm to room temperature, and reacted for 4 h. After that, the reaction solution was poured into dichloromethane (30 mL) and washed with water (220 mL) and saturated sodium chloride solution (20 mL), and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound E as a colorless oily liquid.

[0106] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.45-7.39 (m, 2H), 7.12-7.06 (m, 2H), 3.24 (t, J=5.0 Hz, 2H), 2.61-2.53 (m, 2H), 1.77 (tt, J=8.0, 5.0 Hz, 2H), 1.44 (s, 9H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 156.19, 140.06, 131.22, 129.96, 119.50, 79.52, 40.56, 33.48, 30.67, 28.30. HRMS (TOF-ESI.sup.+) (m/z): C.sub.14H.sub.20BrNO.sub.2 calculated 314.07 [M+H.sup.+]; found: 314.01.

[0107] Compound E (1.02 g, 3.26 mmol), pinacol diborate (993 mg, 3.91 mmol), palladium tetrakis(triphenylphosphine) (151 mg, 0.13 mmol), and potassium acetate (1.60 g, 16.30 mmol) were added to a 100 mL Schlenk bottle in sequence, and then 50 mL of N,N-dimethylformamide was added. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 10 h. After cooling, the reaction mixture was poured into water (50 mL) and extracted with dichloromethane (330 mL). The organic phase was washed with water (330 mL) and saturated sodium chloride solution (30 mL) in turn, and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound F as a colorless oily liquid.

[0108] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.57-7.51 (m, 2H), 7.08 (dt, J=7.4, 1.0 Hz, 2H), 5.94 (t, J=6.4 Hz, 2H), 3.17 (td, J=7.1, 6.4 Hz, 2H), 2.66 (tt, J=7.1, 1.0 Hz, 2H), 1.83 (p, J=7.1 Hz, 2H), 1.42 (s, 9H), 1.24 (s, 9H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 156.63, 143.39, 134.66, 134.61, 126.72, 84.02, 79.63, 39.62, 33.32, 29.09, 29.05, 24.82. HRMS (TOF-ESI.sup.+) (m/z): C.sub.20H.sub.32BNO.sub.4 calculated. 362.25 [M+H.sup.+], found: 362.29.

[0109] Compound A (843 mg, 1.21 mmol), compound F (965 mg, 2.66 mmol), bis(dibenzalacetone) palladium (22.3 mg, 24 mol), tri(o-tolyl)phosphine (29.6 mg, 97.0 mol), and anhydrous potassium carbonate (1.57 g, 11.41 mmol) were added to a 100 mL Schlenk bottle in sequence. After adding 2 drops of aliquat 336, 24 mL of toluene and 6 mL of distilled water were injected. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 24 h. After cooling, the reaction mixture was poured into water (50 mL) and extracted with dichloromethane (330 mL). After the organic phases were combined and dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound G as a purple solid.

[0110] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.76 (d, J=8.6 Hz, 2H), 7.59-7.66 (m, 4H), 7.39 (dd, J=24.6, 7.5 Hz, 2H), 7.16 (ddd, J=8.2, 1.5, 0.5 Hz, 4H), 4.11 (d, J=6.9 Hz, 4H), 3.19 (t, J=6.4 Hz, 4H), 2.39 (t, J=6.8 Hz, 4H), 1.84-2.03 (m, 4H), 1.54-1.76 (m, 2H), 1.43 (s, 18H), 1.15-1.38 (m, 14H), 0.76-0.91 (m, 16H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 172.83, 156.19, 148.85, 145.64, 141.66, 133.63, 132.81, 128.37, 127.67, 126.29, 121.45, 100.02, 79.52, 46.33, 40.56, 38.65, 33.48, 32.60, 32.11, 30.79, 30.67, 29.64, 28.61, 28.30, 25.09, 23.56, 22.79, 14.09, 14.06, 11.51. HRMS (TOF-ESI.sup.+) (m/z): C.sub.59H.sub.80N.sub.4O.sub.6S.sub.2 calculated: 1005.55 [M+H.sup.+]; found: 1005.55.

[0111] The located reaction was carried out according to the method of Example 1, except that compound B was relocated with compound G (0.131 g, 0.13 mmol), to obtain the interested compound 4 as a dark purple solid.

[0112] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.72 (d, J=8.6 Hz, 2H), 7.63 (ddd, J=J=8.5, 1.5, 0.5 Hz, 4H), 7.40 (d, J=8.6, 2H), 7.12-7.19 (m, 4H), 4.07-4.15 (m, 4H), 2.60-2.68 (m, 4H), 2.29-2.37 (t, J=6.6 Hz, 4H), 1.54-1.94 (m, 6H), 1.15-1.38 (m, 14H), 0.76-0.91 (m, 16H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 172.83, 148.85, 145.64, 141.66, 133.63, 132.81, 128.37, 127.67, 126.29, 121.45, 100.02, 46.33, 41.70, 38.65, 33.53, 33.05, 32.60, 32.11, 30.79, 29.64, 28.61, 25.09, 23.56, 22.79, 14.09, 14.06, 11.51. HRMS (TOF-ESI.sup.+) (m/z): calculated: 805.45 [M+H.sup.+]; found: 805.42.

(2) Preparation of Compound 4 Based Single Molecule Field Effect Transistor

[0113] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 4 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 4 was used to replace compound 1.

Example 5: Preparation of Compound 5 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 5

[0114] The synthetic route is as follows:

##STR00017##

[0115] Bis[1,2-bis(diphenylphosphine)ethane]ruthenium dichloride (223 mg, 0.23 mmol), N-Boc-4-ethynylaniline (150 mg, 0.69 mmol), and sodium hexafluorophosphate (154 mg, 0.92 mmol) were added to a 50 mL Schlenk bottle, which was then dissolved in dry dichloromethane (15 mL). Triethylamine (0.190 mL) was added drop wise to the above reaction solution under the protection of argon, which was then reacted at 35 C. with stirring for 24 h. After the reaction was completed, the reaction mixture was filtered. The solvent was removed under reduced pressure. The obtained solid was washed with n-pentane (25 mL). The crude product was analyzed and purified by silica gel column chromatography to obtain compound H as a yellow solid.

[0116] .sup.31P NMR (162 MHz, CDCl.sub.3, 298 K): 53.4. .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 6.98-7.55 (m, 48H), 2.45 (m, 8H), 1.50 (s, 18H). .sup.13C NMR (100 MHz, COCl.sub.3, 298 K): 195.14, 138.85, 132.99, 131.93, 131.20, 131.08, 128.13, 121.56, 119.15, 116.90, 79.54, 30.23, 25.43, HRMS (TOF-ESI+) (m/z): C.sub.78H.sub.76N.sub.2O.sub.4P.sub.4Ru calculated. 1331.44[M+H.sup.+]; found: 1331.39.

[0117] Trifluoroacetic acid (1.0 mL, 0.34 g, 3.73 mmol) was added drop wise to compound H (0.173 g, 0.13 mmol) in dichloromethane (10 mL). After stirring for 20 hours at room temperature, the reaction mixture was added dropwise to saturated aqueous sodium bicarbonate solution (20 mL), and extracted with dichloromethane (50 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (30 mL) and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo to obtain interested compound 5 as a yellow solid.

[0118] .sup.31P NMR (162 MHz, CDCl.sub.3, 298 K): d=53.4 .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 6.98-7.55 (m, 48H), 2.45 (m, 8H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 148.85, 132.99, 131.93, 131.20, 131.08, 128.13, 121.56, 119.15, 116.90, 24.96. HRMS (TOF-ESI+) (m/z): C.sub.68H.sub.60N.sub.2P.sub.4Ru calculated 0.1131.28 [M+H.sup.+]; found: 1131.29.

(2) Preparation of Compound 5 Based Single Molecule Field Effect Transistor

[0119] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 5 based field effect transistor with bottom gate structure based on compound 5 with reference to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 5 was used to replace compound 1.

Example 6: Preparation of Compound 6 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 6

[0120] The synthetic route is as follows:

##STR00018##

[0121] Compound I was synthesized according to the method described in the literature (New J. Chem., 2011, 35, 2105-2113).

[0122] Compound I (527 mg, 0.23 mmol), N-Boc-4-ethynylaniline (150 mg, 0.69 mmol), and sodium hexafluorophosphate (154 mg, 0.92 mmol) were added to a 50 mL Schlenk bottle, which was then dissolved in dry dichloromethane (15 mL). Triethylamine (0.190 mL) was added dropwise to the above reaction solution under the protection of argon, which was then reacted at 35 C. with stirring for 48 h. After the reaction was completed, the reaction mixture was filtered. The solvent was removed under reduced pressure. The obtained solid was washed with n-pentane (25 mL). The crude product was analyzed and purified by silica gel column chromatography to obtain compound J as a yellow solid.

[0123] .sup.31P NMR (162 MHz, CDCl.sub.3, 298 K): 54.9. .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 6.98-7.55 (m, 92H), 2.45 (m, 16H), 1.50 (s, 18H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 195.14, 138.85, 137.24, 132.99, 131.93, 131.20, 131.08, 128.13, 125.60, 121.56, 119.15, 116.90, 79.54, 30.23, 25.43, HRMS (TOF-ESI+) (m/z): C.sub.140H.sub.128N.sub.2O.sub.4P.sub.8Ru.sub.2 calculated. 2353.59 [M+H].sup.+; found: 2353.50.

[0124] The reaction was carried out located according to the method of Example 5, except that compound H was relocated with compound J (0.306 g, 0.13 mmol, to obtain the interested compound 6 as a yellow solid.

[0125] .sup.31P NMR (162 MHz, CDCl.sub.3, 298 K): d=55.4 .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 6.98-7.55 (m, 92H), 2.45 (m, 16H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 150.20, 137.39, 137.23, 132.46, 132.41, 123.20, 122.20, 117.38, 113.78, 103.62, 133.05, 132.92, 128.47, 128.42, 24.96; HRMS (TOF-ESI+) (m/z): C.sub.130H.sub.112N.sub.2P.sub.8Ru.sub.2 calculated: 2153.48 [M+H.sup.+]; found: 2153.49.

(2) Preparation of Compound 6 Based Single Molecule Field Effect Transistor

[0126] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 6 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 6 was used to replace compound 1.

Example 7: Preparation of Compound 7 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 7

[0127] The synthetic route is as follows:

##STR00019##

[0128] Bis[1,2-bis(diphenylphosphine)ethane] ruthenium chloride triflate (825 mg, 0.75 mmol) and N-Boc-4-ethynylaniline (330 mg, 1.52 mmol) were added to a 100 mL Schlenk bottle, and dissolved in 40 mL of dichloromethane. The reaction was stirred at room temperature under the protection of argon for 6 h, and then filtered. The solvent of the filtrate was removed under reduced pressure. The resulting precipitate was washed with ether (430 mL) to obtain compound K as a dark green solid.

[0129] .sup.31P NMR (162 MHz, CDCl.sub.3, 298 K): 38.2. .sup.1H NMR (400 MHz, CDCl.sub.5, 298 K): 7.51-7.05 (m, 40H), 6.55 (d, J=7.8 Hz, 2H), 5.64 (d, J=8.0 Hz, 2H), 4.10 (s, 1H), 2.92 (m, 8H), 1.50 (s, 1811). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 354.27, 194.75, 137.24, 132.99, 131.93, 131.20, 131.08, 128.13, 125.60, 124.93, 120.4, 108.98, 79.54, 30.23, 28.68. HRMS (TOF-ESI+) (m/z): C.sub.66H.sub.63ClF.sub.3NO.sub.5P.sub.4RuS calculated: 1300.21 [M+H.sup.+]; found: 1300.20.

[0130] Compound L was synthesized according to the method described in the literature (New J. Chem., 2011, 35, 2105-2113).

[0131] Compound K (338 mg, 0.26 mmol), Compound L (149 mg, 0.13 mmol), sodium hexafluorophosphate (88 mg, 0.2 mmol) were added to a 50 mL Schlenk bottle, and then dissolved in dry dichloromethane (30 mL). Triethylamine (0.150 mL) was added dropwise to the above reaction solution under the protection of argon, which was then reacted at 35 C. with stirring for 96 h. After the reaction was completed, the reaction mixture was filtered. The solvent was removed under reduced pressure. The obtained solid was washed with n-pentane (25 mL). The crude product was analyzed and purified by silica gel column chromatography to obtain compound M as a yellow solid.

[0132] .sup.31P NMR (162 MHz, CDCl.sub.3, 298 K): 54.89. .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 6.98-7.55 (m, 136H), 2.45 (m, 24H), 1.50 (s, 18H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 195.14, 137.95-126.92, 119.15, 118.42, 116.90, 79.54, 30.23, 25.43, HRMS (TOF-ESI+) (m/z): C.sub.202H.sub.180N.sub.2O.sub.4P.sub.12Ru.sub.3 calculated: 3375.79 [M+H].sup.+; found: 3375.70.

[0133] The reaction was carried out located according to the method of Example 5, except that compound H was relocated with compound M (0.439 g, 0.13 mmol), to obtain the interested compound 7 as a yellow solid.

[0134] .sup.31P NMR (162 MHz, CDCl.sub.3, 298 K): d=55.00, .sup.13C NMR (400 MHz, CDCl.sub.3, 298 K): 6.98-7.55 (m, 136H), 2.45 (m, 24H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 195.14, 137.95-126.92, 119.15, 118.42, 116.90, 25.43; HRMS (TOF-ESI+) (m/z): C.sub.192H.sub.164N.sub.2P.sub.12Ru.sub.3 calculated: 3175.68 [M+H.sup.+]; found: 3175.68.

(2) Preparation of Compound 7 Based Single Molecule Field Effect Transistor

[0135] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 7 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 7 was used to replace compound 1.

Example 8: Preparation of Compound 8 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 8

[0136] The synthetic route is as follows:

##STR00020##

[0137] Dichloromethane (15 mL), 3-bromo-4-aminobiphenyl (1.499 g, 6.04 mmol) and triethylamine (944 mg, 1.3 mL, 9.33 mmol) were added into a 50 mL reaction flask under argon protection, and the reaction flask was located in an ice-water bath. Di-tert-butyl dicarbonate (1.61 g, 1.7 mL, 7.40 mmol) was added dropwise with stirring, allowed to warm to room temperature, and reacted for 4 h. After that, the reaction solution was poured into dichloromethane (30 mL) and washed with water (220 mL) and saturated sodium chloride solution (20 mL) in turn, and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound N as a white solid.

[0138] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.78 (t, J=2.0 Hz, 1H), 7.72-7.65 (m, 2H), 7.62 (dt, J=7.5, 2.0 Hz, 1H), 7.53 (dq, J=8.2, 2.1 Hz, 3H), 7.31 (t, J=7.5 Hz, 1H), 6.57 (s, 1H), 1.50 (s, 9H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 153.93, 143.4.3, 137.44, 136.75, 131.50, 130.90, 130.48, 127.82, 126.46, 126.38, 123.40, 80.43, 28.16. HRMS (TOF-ESI.sup.+) (m/z): C.sub.17H.sub.18BrNO.sub.2 calculated. 348.06 [M+H.sup.+]; found: 348.06.

[0139] Compound O was synthesized according to the method described in the literature (J. Am. Chem. Soc. 2014, 136, 8165-8168).

[0140] Compound N (428 mg, 1.23 mmol), compound O (477 mg, 1.35 mmol), tetrakis(triphenylphosphine) palladium (14.6 mg, 12.3 mol), and anhydrous potassium carbonate (1.60 g, 11.6 mmol) were added to a 100 mL Schlenk bottle in sequence, and then 25 mL of tetrahydrofuran and 5 mL of distilled water were injected. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 24 h. After cooling, the reaction mixture was poured into water (50 mL) and extracted with dichloromethane (330 mL). After the organic phases were combined and dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound P as a white solid.

[0141] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.58 (dd, J=10.2, 1.1 Hz, 2H), 8.55-8.48 (m, 4H), 8.08 (t, J=2.0 Hz, 1H), 8.01 (t, J=2.0 Hz, 1H), 7.80-7.55 (m, 10H), 7.48 (td, J=7.9, 1.2 Hz, 2H), 6.93 (ddd, J=8.0, 5.1, 1.1 Hz, 2H), 6.59 (s, 1H), 1.50 (s, 9H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 156.38, 155.79, 153.93, 149.14, 147.56, 142.54, 140.08, 139.77, 138.84, 137.44, 136.75, 136.59, 129.45, 129.37, 129.27, 128.17, 128.05, 127.82, 127.76, 126.46, 125.60, 124.02, 121.39, 120.06, 80.43, 28.16. HRMS (TOF-ESI.sup.+) (m/z): C.sub.38H.sub.32N.sub.4O.sub.2 calculated. 577.26 [M+H.sup.+]; found: 577.26.

[0142] Methanol (10 mL) was added to a 50 mL reaction flask to dissolve compound P (182 mg, 0.316 mmol). After that, ferrous chloride (21 mg, 0.158 mmol) in methanol (10 mL) was added dropwise, and the reactant was stirred and refluxed under the protection of argon for 4 h. Then the reactant was cooled to room temperature, and an excess of saturated ammonium hexafluorophosphate in methanol was added dropwise until the precipitation was completely precipitated, which was filtered. The obtained solid was rinsed with distilled water (210 mL) and ether (210 mL) in turn. The crude product was recrystallized with a mixed solvent of acetonitrile and acetone to obtain compound Q as a purple solid.

[0143] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8 8.85 (dd, J=7.5, 1.4 Hz, 4H), 8.69 (d, J=8.0 Hz, 8H), 8.04 (t, J=2.0 Hz, 4H), 7.76 (dd, J=8.1, 6.7 Hz, 4H), 7.71-7.49 (m, 20H), 7.00 (td, J=7.4, 1.6 Hz, 4H), 1.50 (s, 18H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 195.12, 155.16, 153.93, 152.39, 150.10, 149.69, 142.54, 140.08, 139.77, 138.84, 138.67, 137.44, 136.75, 129.45, 129.37, 129.27, 128.17, 128.05, 127.82, 127.76, 126.46, 125.60, 125.08, 122.82, 80.43, 28.16. HRMS (TOF-ESI.sup.+) (m/z): C.sub.76H.sub.64FeN.sub.8O.sub.4 calculated: 1029.44 [M2PF.sub.6.sup.+H.sup.+]; found. 1029.44.

[0144] Trifluoroacetic acid (1.0 mL, 0.34 g, 3.73 mmol) was added dropwise to compound Q (0.135 g, 0.13 mmol) in dichloromethane (10 mL). After stirring for 20 hours at room temperature, the reaction mixture was added dropwise to saturated aqueous sodium bicarbonate solution (20 mL), and extracted with dichloromethane (50 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (30 mL) and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo to obtain interested compound 8 as a purple solid.

[0145] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.43-8.52 (m, 12H), 8.05 (t, J=2.0 Hz, 2H), 7.97 (t, J=2.0 Hz, 2H), 7.79-7.58 (m, 12H), 7.48 (td, J=8.0, 1.3 Hz, 4H), 7.31-7.25 (m, 4H), 6.93 (ddd, J=8.0, 5.1, 1.1 Hz, 4H), 6.79-6.73 (m, 4H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K) 156.38, 155.79, 149.14, 148.03, 147.56, 142.54, 140.08, 139.77, 138.84, 136.59, 134.36, 129.45, 129.37, 129.27, 128.17, 128.15, 128.05, 127.76, 125.60, 124.02, 121.39, 120.06, 115.37. HRMS (TOF-ESI.sup.+) (m/z): C.sub.66H.sub.48FeN.sub.8 calculated: 1009.34 [M2PF.sub.6.sup.+H.sup.+], found: 1009.34.

(2) Preparation of Compound 8 Based Single Molecule Field Effect Transistor

[0146] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 8 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 8 was used to replace compound 1.

Example 9: Preparation of Compound 9 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 9

[0147] The synthetic route is as follows:

##STR00021##

[0148] Methanol (10 mL) was added to a 50 mL reaction flask to dissolve compound P (182 mg, 0.316 mmol). After that, zinc chloride (26 mg, 0.158 mmol) in methanol (10 mL) was added dropwise, and the reactant was stirred and refluxed under the protection of argon for 4 h. Then the reactant was cooled to room temperature, and an excess of saturated ammonium hexafluorophosphate in methanol was added dropwise until the precipitation was completely precipitated, which was filtered. The obtained solid was rinsed with distilled water (2*10 mL) and ether (2*10 mL) in turn. The crude product was recrystallized with a mixed solvent of acetonitrile and acetone to obtain compound R.

[0149] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.75 (dd, J=7.5, 1.4 Hz, 4H), 8.59 (d, J=8.0 Hz, 8H), 7.94 (t, J=2.0 Hz, 4H), 7.66 (dd, J=8.1, 6.7 Hz, 4H), 7.61-7.39 (m, 20H), 7.00 (td, J=7.4, 1.6 Hz, 4H), 1.50 (s, 18H).sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 195.12, 156.16, 153.93, 152.39, 151.10, 149.69, 142.64, 140.08, 139.77, 138.88, 138.77, 137.44, 136.75, 129.45, 129.37, 129.27, 128.17, 128.15, 127.82, 127.76, 126.46, 125.60, 125.08, 122.82, 80.43, 28.16. HRMS (TOF-ESI.sup.+) (m/z): C.sub.76H.sub.64ZnN.sub.8O.sub.4 calculated: 1017.45 [M2PF.sub.6.sup.+H.sup.+]; found: 1017.45.

[0150] The reaction was carried out located according to the method of Example 8, except that compound Q was relocated with compound R (0.158 g, 0.13 mmol), to obtain the interested compound 9.

[0151] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.43-8.52 (m, 12H), 8.05 (t, J=2.0 Hz, 2H), 7.97 (t, J=2.0 Hz, 2H), 7.79-7.58 (m, 12H), 7.48 (td, J=8.0, 1.3 Hz, 4H), 7.31-7.25 (m, 4H), 6.93 (ddd, J=8.0, 5.1, 1.1 Hz, 4H), 6.79-6.73 (m, 4H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K) 156.38, 155.79, 149.14, 148.03, 147.56, 142.54, 140.08, 139.77, 138.84, 136.59, 134.36, 129.45, 129.37, 129.27, 128.17, 128.15, 128.05, 127.76, 125.60, 124.02, 121.39, 120.06, 115.37. HRMS (TOF-ESI.sup.+) (m/z): C.sub.60H.sub.48ZnN.sub.8 calculated: 1017.33 [M2PF.sub.6.sup.+H.sup.+]; found: 1017.34.

(2) Preparation of Compound 9 Based Single Molecule Field Effect Transistor

[0152] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 9 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 9 was used to replace compound 1.

Example 10: Preparation of Compound 10 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 10

[0153] The synthetic route is as follows:

##STR00022##

[0154] Methanol (10 mL) was added to a 50 mL reaction flask to dissolve compound P (182 mg, 0.316 mmol). After that, ruthenium chloride (33 mg, 0.158 mmol) in methanol (10 mL) was added dropwise, and the reactant was stirred and refluxed under the protection of argon for 4 h. Then the reactant was cooled to room temperature, and an excess of saturated ammonium hexafluorophosphate in methanol was added dropwise until the precipitation was completely precipitated, which was filtered. The obtained solid was rinsed with distilled water (210 mL) and ether (210 mL) in turn. The crude product was recrystallized with a mixed solvent of acetonitrile and acetone to obtain compound S as a red solid.

[0155] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 9.05 (dd, J=7.5, 1.4 Hz, 4H), 8.79 (d, J=8.0 Hz, 8H), 8.14 (t, J=2.0 Hz, 4H), 7.76 (dd, J=8.1, 6.7 Hz, 4H), 7.71-7.49 (m, 20H), 7.10 (td, J=7.4, 1.6 Hz, 4H), 1.50 (s, 18H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 195.12, 155.16, 153.93, 152.39, 150.10, 149.69, 142.54, 141.08, 139.77, 138.94, 138.67, 137.44, 136.75, 129.45, 129.37, 129.27, 128.17, 128.15, 127.82, 127.76, 126.46, 125.60, 125.08, 122.82, 80.43, 28.16. HRMS (TOF-ESI.sup.+) (m/z): C.sub.76H.sub.64RuN.sub.8O.sub.4 calculated: 1255.40 [M2PF.sub.6.sup.+H.sup.+]; found: 1255.40.

[0156] The located reaction was carried out according to the method of Example 8, except that compound Q was relocated with compound S (0.164 g, 0.13 mmol), to obtain the interested compound 10 as a red solid.

[0157] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.63-8.72 (m, 12H), 8.25 (t, J=2.0 Hz, 2H), 8.17 (t, J=2.0 Hz, 2H), 7.89-7.68 (m, 12H), 7.68 (td, J=8.0, 1.3 Hz, 4H), 7.31-7.25 (m, 4H), 6.93 (ddd, J=8.0, 5.1, 1.1 Hz, 4H), 6.79-6.73 (m, 4H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K) 156.38, 155.79, 149.14, 148.03, 147.56, 142.54, 140.08, 139.77, 138.84, 136.59, 134.36, 129.45, 129.37, 129.27, 128.17, 128.15, 128.05, 127.76, 125.60, 124.02, 121.39, 120.06, 115.37. HRMS (TOF-ESI.sup.+) (m/z): C.sub.66H.sub.48RuN.sub.8 calculated: 1055.31 [M2PF.sub.6.sup.+H.sup.+]; found: 1055.31.

(2) Preparation of Compound 10 Based Single Molecule Field Effect Transistor

[0158] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 10 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 10 was used to replace compound 1.

Example 11: Preparation of Compound 11 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 11

[0159] The synthetic route is as follows:

##STR00023## ##STR00024##

[0160] 4-(Boc-amino) benzaldehyde (2.212 g, 10 mmol) and acetophenone (2.403 g, 20 mmol) were added to a reaction flask under the protection of argon. Boron trifluoride ether (4.258 g, 30 mmol) was added dr op wise with stirring, which was reacted at 100 C. for 3 h. After that, the reaction solution was cooled to room temperature, poured into ether (200 mL), and filtered to obtain the precipitated solid, which was recrystallized with absolute ethanol to obtain compound T as a yellow solid.

[0161] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.91-8.85 (m, 6H), 7.80-7.72 (m, 4H), 7.47-7.41 (m, 2H), 7.23 (tt, J=7.4, 2.0 Hz, 2H), 6.56-6.50 (m, 2H), 1.50 (s, 9H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K) 168.71, 166.14, 153.93, 137.71, 133.99, 132.58, 131.06, 130.95, 129.13, 127.95, 126.42, 115.21, 80.43, 28.16. HRMS (TOF-ESI+) (m/z): C28H26NO3 calculated: 425.19 [MBF4.sup.+H+]; found: 425.19.

[0162] Compound T (511 mg, 1 mmol) was added to a reaction flask under the protection of argon, and dissolved with tetrahydrofuran (5 mL). After that, p-bromoaniline (172 mg, 1 mmol) was added. The reactant was refluxed for 4 h, cooled to room temperature. Ethanol was added for recrystallization, to obtain compound U.

[0163] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.89-7.81 (m, 4H), 7.59-7.53 (m, 2H), 7.52-7.46 (m, 6H), 7.41 (qd, J=3.8, 1.5 Hz, 611), 7.19-7.13 (m, 2H), 1.50 (s, 9H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K) 156.07, 153.93, 140.59, 137.71, 136.23, 134.01, 132.14, 130.72, 129.94, 129.48, 128.57, 128.09, 127.95, 126.43, 126.40, 120.79, 80.43, 28.16. HRMS (TOF-ESI.sup.+)(m/z): C.sub.34H.sub.30BrN.sub.2O.sub.2 calculated: 578.16[MBF.sub.4.sup.+H.sup.+]; found: 578.16.

[0164] Compound V was synthesized according to the method described in the literature (J. Am. Chem. Soc. 2012, 134, 7672-7675).

[0165] Compound U (710 mg, 1.23 mmol), compound V (477 mg, 1.35 mmol), tetrakis(triphenylphosphine) palladium (14.6 mg, 12.3 mol), and anhydrous potassium carbonate (1.60 g, 11.6 mmol) were added to a 100 mL Schlenk bottle in sequence, and then 25 mL of tetrahydrofuran and 5 mL of distilled water were injected. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 24 h. After cooling, the reaction mixture was poured into water (50 mL) and extracted with dichloromethane (330 mL). After the organic phases were combined and dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound W.

[0166] .sup.1H NMR (400 MHz, CDCl.sub.3, 298K) 8.81 (dd, J=8.0, 1.0 Hz, 2H), 8.58 (s, 2H), 8.52 (dd, J=5.0, 1.3 Hz, 2H), 7.90-7.81 (m, 10H), 7.59-7.52 (m, 4H), 7.52-7.45 (m, 6H), 7.41 (qd, J=3.8, 1.5 Hz, 6H), 6.93 (ddd, J=8.0, 5.1, 1.1 Hz, 2H), 1.50 (s, 9H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K) 156.72, 156.07, 155.79, 153.93, 149.49, 149.14, 142.53, 141.53, 138.74, 137.71, 136.59, 136.23, 135.65, 134.01, 131.13, 130.72, 129.94, 129.48, 128.90, 128.09, 127.95, 127.79, 127.28, 126.43, 126.40, 124.02, 121.39, 118.36, 80.43, 28.16 HRMS (TOF-ESI.sup.+)(m/z). C.sub.55H.sub.44N.sub.5O.sub.2 calculated: 807.34 [MBF.sub.4.sup.+H.sup.+]; found: 807.34.

[0167] Methanol (10 mL) was added to a 50 mL reaction flask to dissolve compound W (282 mg, 0.316 mmol). After that, ruthenium chloride (33 mg, 0.158 mmol) in methanol (10 mL) was added dropwise, and the reactant was stirred and refluxed under the protection of argon for 4 h. Then the reactant was cooled to room temperature, and an excess of saturated ammonium hexafluorophosphate in methanol was added dropwise until the precipitation was completely precipitated, which was filtered. The obtained solid was rinsed with distilled water (210 mL) and ether (210 mL) in turn. The crude product was recrystallized with a mixed solvent of acetonitrile and acetone to obtain compound X as a red solid.

[0168] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.75 (dd, J=7.5, 1.4 Hz, 4H), 8.59 (d, J=8.0 Hz, 8H), 7.90-7.81 (m, 20H), 7.59-7.52 (m, 8H), 7.51-7.37 (m, 25H), 7.00 (td, J=7.4, 1.6 Hz, 4H), 1.50 (s, 18H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 156.07, 154.69, 153.93, 151.96, 150.33, 149.96, 142.53, 141.53, 138.80, 138.75, 137.71, 136.23, 135.65, 134.01, 131.13, 130.72, 129.94, 129.67, 129.48, 128.90, 128.09, 127.95, 127.79, 127.28, 126.43, 126.40, 125.48, 124.07, 80.43, 28.16. HRMS (TOF-ESI.sup.+) (m/z): C.sub.110H.sub.88N.sub.10O.sub.4Ru calculated: 1715.61 [M2BF.sub.4.sup.2PF.sub.6.sup.+H.sup.+]; found: 1715.61.

[0169] The reaction was carried out located according to the method of Example 8, except that compound Q was relocated with compound X (0.283 g, 0.13 mmol), to obtain the interested compound 11 as a red solid.

[0170] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.75 (dd, J=7.5, 1.6 Hz, 4H), 8.60-8.56 (m, 8H), 7.90-7.81 (m, 20H), 7.58-7.52 (m, 4H), 7.48 (s, 4H), 7.46-7.37 (m, 16H), 7.21-7.15 (m, 4H), 7.00 (td, J=7.4, 1.6 Hz, 4H), 6.81-6.75 (m, 4H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K) 156.07, 154.69, 151.96, 150.33, 149.96, 148.03, 142.53, 141.53, 138.80, 138.74, 136.23, 135.65, 134.01, 131.13, 130.72, 129.94, 129.67, 129.48, 128.90, 128.22, 128.09, 127.79, 127.28, 125.48, 125.32, 124.07, 115.05. HRMS (TOF-ESI.sup.+) (m/z): C.sub.100H.sub.72N.sub.10Ru calculated. 1515.50 [M2BF.sub.4.sup.2PF.sub.6.sup.+H.sup.+]; found: 1515.50.

(2) Preparation of Compound 11 Based Single Molecule Field Effect Transistor

[0171] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 11 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 11 was used to replace compound 1.

Example 12: Preparation of Compound 12 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 12

[0172] The synthetic route is as follows:

##STR00025## ##STR00026##

[0173] 1,3-dibromo-5-iodobenzene (1.092 g, 3.02 mmol), 4-(Boc-amino)phenylboronic acid (455 mg, 3.32 mmol), palladium tetrakis(triphenylphosphine) (34.9 mg, 30.3 mol), and anhydrous potassium carbonate (3.93 g, 28.5 mmol) were added to a 250 mL Schlenk bottle in sequence, and then 60 mL of tetrahydrofuran and 15 mL of distilled water were injected. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 24 h. After cooling, the reaction mixture was poured into water (200 mL) and extracted with dichloromethane (360 mL). After the organic phases were combined and dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound Y.

[0174] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 7.76 (q, J=1.4 Hz, 3H), 7.72-7.65 (m, 2H), 7.56-7.50 (m, 2H), 6.57 (s, 1H), 1.50 (s, 9H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K) 153.93, 143.19, 137.71, 134.00, 128.66, 127.95, 126.42, 123.44, 80.43, 28.16. HRMS (TOF-ESI.sup.+) (m/z): C.sub.17H.sub.17Br.sub.2NO.sub.2 calculated: 425.97 [M+H.sup.+]; found. 425.97.

[0175] Compound Y (522 mg, 1.23 mmol), compound O (477 mg, 1.35 mmol), tetrakis(triphenylphosphine) palladium (14.6 mg, 12.3 mol), and anhydrous potassium carbonate (1.60 g, 11.6 mmol) were added to a 100 mL Schlenk bottle in sequence, and then 25 mL of tetrahydrofuran and 5 mL of distilled water were injected. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 24 h. After cooling, the reaction mixture was poured into water (50 mL) and extracted with dichloromethane (330 mL). After the organic phases were combined and dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound Z.

[0176] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.70-8.44 (m, 12H), 8.31 (dt, J=3.5, 2.0 Hz, 211), 8.23 (t, J=2.0 Hz, 111), 8.17 (t, J=2.0 Hz, 1H), 8.12 (t, J=1.9 Hz, 1H), 7.83-7.59 (m, 11H), 7.48 (td, J=8.0, 1.3 Hz, 4H), 6.93 (ddd, J=8.0, 5.1, 1.1 Hz, 4H), 1.50 (s, 9H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K) 156.38, 155.79, 153.93, 149.14, 147.56, 141.72, 141.37, 138.86, 137.71, 136.59, 133.99, 129.37, 129.27, 129.18, 128.16, 127.95, 126.42, 124.02, 121.39, 120.06, 80.43, 28.16. HRMS (TOF-ESI.sup.+) (m/z): C.sub.59H.sub.45N.sub.7O.sub.2 calculated: 884.35 [M+H.sup.+]; found: 884.35.

[0177] Methanol (10 mL) was added to a 50 mL reaction flask to dissolve compound Z (280 mg, 0.316 mmol). After that, ferrous chloride (21 mg, 0.158 mmol) in methanol (10 mL) was added dropwise, and the reactant was stirred and refluxed under the protection of argon for 4 h. Then the reactant was cooled to room temperature, and an excess of saturated ammonium hexafluorophosphate in methanol was added dropwise until the precipitation was completely precipitated, which was filtered. The obtained solid was rinsed with distilled water (210 mL) and ether (210 mL) in turn. The crude product was recrystallized with a mixed solvent of acetonitrile and acetone to obtain compound Z2 as a purple solid.

[0178] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.75 (dd, J=7.5, 1.4 Hz, 8H), 8.59 (d, J=8.0 Hz, 15H), 8.04 (s, 6H), 7.94 (t, J=2.0 Hz, 4H), 7.66-7.42 (m, 28H), 1.50 (s, 18H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 155.16, 153.93, 152.39, 150.10, 149.69, 141.72, 141.37, 138.86, 138.67, 137.71, 133.99, 129.45, 129.37, 129.27, 129.18, 128.16, 127.95, 126.42, 125.08, 122.82, 80.43, 28.16. HRMS (TOF-ESI.sup.+) (m/z): C.sub.118H.sub.90Fe.sub.2N.sub.14O.sub.4 calculated: 1879.58 [M2PF.sub.6.sup.+H.sup.+]; found: 1879.58.

[0179] The reaction was carried out located according to the method of Example 8, except that compound Q was relocated with compound Z2 (0.282 g, 0.13 mmol), to obtain the interested compound 12 as a purple solid.

[0180] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.75 (dd, J=7.5, 1.6 Hz, 8H), 8.60-8.56 (m, 15H), 8.04 (s, 6H), 7.94 (t, J=2.0 Hz, 4H), 7.66 (dd, J=8.0, 6.7 Hz, 4H), 7.58 (dd, J=7.2, 2.0 Hz, 8H), 7.43 (td, J=7.4, 1.6 Hz, 8H), 7.21-7.15 (m, 4H), 7.00 (td, J=7.4, 1.6 Hz, 8H), 6.81-6.75 (m, 4H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K) 155.16, 152.39, 150.10, 149.69, 148.03, 141.72, 141.37, 138.86, 138.67, 131.31, 129.45, 129.37, 129.27, 129.18, 128.27, 128.16, 125.08, 122.82, 115.05. HRMS (TOF-ESI.sup.+) (m/z): C.sub.108H.sub.74Fe.sub.2N.sub.14 calculated: 1679.50 [M2PF.sub.6.sup.+H.sup.+]; found: 1679.50.

(2) Preparation of Compound 12 Based Single Molecule Field Effect Transistor

[0181] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 12 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 12 was used to replace compound 1.

Example 13: Preparation of Compound 13 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 13

[0182] The synthetic route is as follows:

##STR00027##

Compound Z3 was synthesized according to the route in the literature (European Journal of Medicinal Chemistry, 102, 277-287; 2015).

[0183] Compound Z4 was synthesized according to the route in the literature (Journal of the American Chemical Society, 136(10), 3972-3980; 2014).

[0184] Compound Z3 (0.279 g, 1 mmol), compound Z4 (0.878 g, 2.4 mmol), Pd(PPh.sub.3).sub.4 (83 mg, 0.072 mmol) and K.sub.2CO.sub.3 (1.0 g, 7.2 mmol) were added to a 100 mL Schlenk bottle in sequence, and then THF/H.sub.2O (20 mL/4 mL) was injected. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 24. After cooling, the reaction mixture was poured into water (50 mL) and extracted with dichloromethane (330 mL). The organic phases were combined and dried with Na.sub.2SO.sub.4 and the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound Z5 as a yellow solid.

[0185] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.11-7.96 (m, 6H), 7.92-7.80 (m, 6H), 7.80-7.61 (m, 6H), 3.92 (s, 4H), 3.75 (s, 6H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 172.68, 137.95, 133.76, 132.68, 131.30, 129.89, 129.08, 128.51, 128.06, 127.35, 127.06, 125.89, 123.71, 123.64, 51.97, 40.77. HRMS (TOF-ESI+) (m/z): C.sub.36H.sub.28O.sub.4 calculated: 525.21 [M+H.sup.+]; found: 525.21.

[0186] Compound Z5 (0.488 g, 0.93 mmol) was added to 5 mL of 28% ammonia water, and the reaction was stirred at room temperature for 24 h. After that, th reactant was extracted with dichloromethane (3*10 mL). The organic phases were combined and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound Z6 as a yellow solid.

[0187] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.12-7.96 (m, 6H), 7.92-7.67 (m, 12H), 3.63 (s, 4H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 172.58, 137.95, 135.09, 133.06, 131.30, 130.40, 128.51, 128.35, 128.06, 127.67, 125.89, 125.49, 123.71, 123.64, 41.07. HRMS (TOF-ESI+) (m/z): C.sub.34H.sub.26N.sub.2O.sub.2 calculated: 495.21 [M+H.sup.+]; found: 495.21.

[0188] After LiAlH.sub.4 (0.152 g, 4 mmol) and anhydrous THF (5 mL) were added to a reaction flask, a solution of compound Z6 (0.198 g, 0.4 mmol) in anhydrous THF (1 mL) was added dropwise. The reactant was then refluxed for 24 h, and cooled to room temperature. Water was added to quench the reaction. The resultant was extracted with dichloromethane (310 mL). The organic phases were combined and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound 13 as a yellow solid.

[0189] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.11-7.96 (m, 6H), 7.92-7.80 (m, 6H), 7.80-7.61 (m, 6H), 2.53 (s, 4H), 1.24 (s, 4H). .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 137.95, 133.79, 131.30, 130.12, 128.64, 128.51, 128.06, 126.36, 125.89, 125.43, 123.71, 123.64, 43.70, 39.10. HRMS (TOF-ESI+) (m/z): C.sub.34H.sub.30N.sub.2 calculated. 467.25 [M+H.sup.+]; found: 467.25.

(2) Preparation of Compound 13 Based Single Molecule Field Effect Transistor

[0190] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 13 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 13 was used to replace compound 1.

Example 14: Preparation of Compound 14 Based Single Molecule Field Effect Transistor

(1) Synthesis of Compound 14

[0191] The synthetic route is as follows:

##STR00028## ##STR00029##

[0192] Compound Z7 was synthesized according to the route in the literature (Chemistry-a European Journal, 2001, 7(22): 4894-4901).

[0193] Compound Z7 (1.00 g, 0.69 mmol), copper iodide (0.572 g, 0.30 mmol), tetrakis(triphenylphosphine) palladium (0.182 g, 0.16 mmol), methyl propiolate (0.060 g, 0.71 mmol) and piperidine (60 mL) were added to a 250 mL Schlenk bottle. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 24 h. After cooling, the reaction mixture was poured into water (50 mL) and extracted with dichloromethane (330 mL). The organic phases were combined and dried with Na.sub.2SO.sub.4 and the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound Z8 as a yellow solid.

[0194] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.40 (s, 2H), 8.13 (s, 2H), 8.02 (s, 2H), 7.99 (s, 2H), 7.98 (s, 2H), 7.86 (s, 2H), 3.75 (s, 3H), 1.26 (m, 88H), 0.92-0.86 (m, 12H).sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 173.44, 139.29, 139.13, 139.10, 129.83, 129.02, 128.96, 128.81, 128.45, 123.60, 123.21, 122.48, 122.29, 120.92, 120.65, 120.53, 120.45, 119.08, 118.94, 118.68, 118.17, 89.82, 82.48, 51.06, 37.29, 37.20, 34.02, 32.45, 32.39, 32.05, 31.98, 30.31, 30.27, 30.10, 30.04, 29.96, 29.88, 29.54, 29.45, 29.41, 25.09, 22.88, 20.15, 14.19.

[0195] HRMS (TOF-ESI+) (m/z): C.sub.94H.sub.115BrO.sub.2 calculated: 1355.81 [M+H.sup.+]; found: 1355.81.

[0196] Compound Z8 (1.10 g, 0.81 mmol), pinacol diborate (0.124 g, 0.49 mmol), palladium tetrakis(triphenylphosphine) (0.038 g, 0.03 mmol), and potassium acetate (0.40 g, 4.07 mmol) were added to a 250 mL Schlenk bottle in sequence, and then 50 mL of N,N-dimethylformamide was added. The resultant was circulated 3 times by a freezing and thawing pump circulation method to remove oxygen, and then heated and stirred at 90 C. under the protection of argon for 10 h. After cooling, the reaction mixture was poured into water (50 mL) and extracted with dichloromethane (330 mL). The organic phase was washed with water (330 mL) and saturated sodium chloride solution (30 mL) in turn, and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound Z9 as a yellow solid.

[0197] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.50 (s, 4H), 8.23 (s, 4H), 8.18 (s, 4H), 8.09 (s, 4H), 7.98 (s, 4H), 7.88 (s, 4H), 3.75 (s, 6H), 1.26 (m, 176H), 0.92-0.86 (m, 24H).

[0198] .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 175.49, 149.45, 139.93, 138.10, 129.81, 129.02, 128.96, 128.81, 128.45, 124.60, 124.21, 124.48, 123.39, 121.92, 121.65, 121.53, 120.45, 119.28, 118.94, 118.68, 118.27, 89.87, 82.58, 51.06, 37.29, 37.20, 34.02, 32.45, 32.39, 32.05, 31.98, 30.31, 30.27, 30.10, 30.04, 29.96, 29.88, 29.54, 29.45, 29.41, 25.09, 22.88, 20.15, 14.19.

[0199] HRMS (TOF-ESI+) (m/z): C.sub.188H.sub.230O.sub.4 calculated. 2552.78 [M+H.sup.+]; found: 2552.78.

[0200] Compound Z9 (663 mg, 0.26 mmol) was dissolved in THF (200 mL), and then Pd/C (10%, 285 mg) was added. H.sub.2 (1 bar) was introduced at room temperature, and the reaction was stirred for 16 h. After the catalyst was removed by filtration, the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound Z10 as a yellow solid.

[0201] .sup.1HNMR (400 MHz, CDCl.sub.3, 298 K): 8.50 (s, 4H), 8.23 (s, 4H), 8.18 (s, 4H), 8.09 (s, 4H), 7.98 (s, 4H), 7.88 (s, 4HL 3.75 (s, 6H), 1.26 (m, 180H), 2.28 (t, J=7.5 Hz, 4H), 0.92-0.86 (m, 24H).

[0202] .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 173.53, 139.42, 129.36, 122.91, 120.78, 119.15, 52.15, 37.29, 33.99, 32.51, 32.37, 32.04, 30.21, 30.05, 30.01, 29.93, 29.85, 29.76, 29.53, 29.48, 29.31, 25.02, 22.86, 14.18.

[0203] HRMS (TOF-ESI+) (m/z): C.sub.188H.sub.238O.sub.4 calculated: 2560.84 [M+H.sup.+]; found: 2560.84.

[0204] Compound Z10 (0.589 g, 0.23 mmol) was added to 5 mL of 28% ammonia water, and the reaction was stirred at room temperature for 24 h, then extracted with dichloromethane (310 mL). The organic phases were combined and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound Z11 as a yellow solid.

[0205] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.50 (s, 4H), 8.23 (s, 4H), 8.18 (s, 4H), 8.07 (s, 4H), 7.96 (s, 4H), 7.86 (s, 4H), 1.26 (m, 180H), 2.28 (t, J=7.5 Hz, 4H), 0.92-0.86 (m, 24H).sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 173.53, 139.42, 129.36, 122.91, 120.78, 119.15, 51.05, 37.29, 33.99, 32.51, 32.37, 32.04, 30.21, 30.05, 30.01, 29.93, 29.85, 29.76, 29.53, 29.48, 29.31, 25.02, 22.86, 14.18.

[0206] HRMS (TOF-ESI+) (m/z): C.sub.186H.sub.236N.sub.2O.sub.2 calculated: 2530.85 [M+H.sup.+]; found: 2530.85.

[0207] After LiAlH.sub.4 (0.152 g, 4 mmol) and anhydrous THF (50 mL) were added to a reaction flask, a solution of compound Z11 (0.506 g, 0.20 mmol) in anhydrous THF (50 mL) was added dropwise. The reactant was then refluxed for 24 h, and cooled to room temperature. Water was added to quench the reaction. The resultant was extracted with dichloromethane (330 mL). The organic phase were combined and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The crude product was analyzed and purified by silica gel column chromatography to obtain compound 14 as a yellow solid.

[0208] .sup.1H NMR (400 MHz, CDCl.sub.3, 298 K): 8.50 (s, 4H), 8.23 (s, 4H), 8.18 (s, 4H), 8.07 (s, 4H), 7.96 (s, 4H), 7.86 (s, 4H), 1.26 (m, 192H), 0.92-0.86 (m, 24H) .sup.13C NMR (100 MHz, CDCl.sub.3, 298 K): 173.53, 139.42, 129.36, 122.91, 120.78, 119.15, 54.05, 48.67, 38.29, 33.89, 32.51, 32.35, 31.84, 30.61, 30.05, 30.01, 29.93, 29.85, 29.76, 29.53, 29.48, 29.31, 25.01, 22.84, 14.19. HRMS (TOF-ESI+) (m/z): C.sub.186H.sub.240N.sub.2 calculated: 2502.89 [M+H.sup.+]; found: 2502.89.

(2) Preparation of Compound 14 Based Single Molecule Field Effect Transistor

[0209] A strongly-polarized molecule-graphene molecular heterojunction was constructed to obtain a compound 14 based field effect transistor with bottom gate structure according to the preparation method of transistor in Example 1, in which graphene was used as the gate electrode, hafnium oxide with a thickness of 5 nm was used as the dielectric layer, and compound 14 was used to replace compound 1.

Example 15: Preparation of Compound 1 Based Single Molecule Field Effect Transistor

[0210] Graphene was used as the gate electrode, and zirconium oxide with a thickness of 5 nm was used as the dielectric layer to construct a field effect transistor with a bottom gate structure.

[0211] First, a bottom gate was formed on the silicon wafer according to the method described in Example 1.

[0212] A zirconium oxide layer with a thickness of 5 nm was deposited on the bottom gate by the electron beam evaporation deposition method.

[0213] According to the method described in Example 1, a strongly-polarized molecule-graphene molecule heterojunction was constructed on the dielectric layer to obtain a single molecule field effect transistor device.

Example 16: Preparation of Compound 1 Based Single Molecule Field Effect Transistor

[0214] Graphene was used as the gate electrode, and titanium oxide with a thickness of 5 nm was used as the dielectric layer to construct a field effect transistor with a bottom gate structure.

[0215] First, a bottom gate was formed on the silicon wafer according to the method described in Example 1.

[0216] A titanium oxide layer with a thickness of 5 nm was deposited on the bottom gate by the electron beam evaporation deposition method.

[0217] According to the method described in Example 1, a strongly-polarized molecule-graphene molecule heterojunction was constructed on the dielectric layer to obtain a single molecule field effect transistor device.

Example 17: Preparation of Compound 1 Based Single Molecule Field Effect Transistor

[0218] Aluminum was used as the gate electrode, and aluminium oxide with a thickness of 5 nm was used as the dielectric layer to construct a field effect transistor with a bottom gate structure.

[0219] First, an aluminum layer with a thickness of 35 nm was deposited on the silicon wafer by electron beam evaporation deposition method. After that, it was heated at 180 C. for 1 hour to prepare an aluminum oxide layer with a thickness of 5 nm.

[0220] According to the method described in Example 1, a strongly-polarized molecule-graphene molecule heterojunction was constructed on the dielectric layer to obtain a single molecule field effect transistor device.

Example 18: Preparation of Compound 1 Based Single Molecule Field Effect Transistor

[0221] Aluminum was used as the gate electrode, and aluminium oxide with a thickness of 3 nm and hafnium oxide with a thickness of 2 nm were used as the dielectric layer to construct a field effect transistor with a bottom gate structure.

[0222] First, an aluminum layer with a thickness of 35 nm was deposited on the silicon wafer by electron beam evaporation deposition method. After that, it was located in the atmosphere for 24 hours, and naturally oxidized to obtain an aluminum oxide layer with a thickness of 3 nm, and then a hafnium oxide layer with a thickness of 2 nm was deposited by atomic layer deposition.

[0223] According to the method described in Example 1, a strongly-polarized molecule-graphene molecule heterojunction was constructed on the hafnium oxide layer to obtain a single molecule field effect transistor device.

Example 19: Preparation of Compound 1 Based Single Molecule Field Effect Transistor

[0224] Example 19 differs from Example 15 in that the thickness of zirconium oxide was 3 nm.

Example 20: Preparation of Compound 1 Based Single Molecule Field Effect Transistor

[0225] Example 20 differs from Example 15 in that the thickness of zirconium oxide was 10 nm.

Example 21: Preparation of Compound 2 Based Single Molecule Field Effect Transistor

[0226] Graphene was used as the gate electrode, and hafnium oxide with a thickness of 5 nm was used as the dielectric layer to construct a field effect transistor with a top gate structure.

[0227] With reference to the method described in Example 1, a strongly-polarized molecule-graphene molecule heterojunction was constructed on a silicon wafer having an oxide layer with a thickness of 300 nm.

[0228] On another silicon wafer, a hafnium oxide layer with a thickness of 5 nm was prepared by the sol-gel method. After that, the graphene grown by chemical vapor deposition was transferred thereon, on which PMMA was further spin-coated. Finally, the silicon wafer was etched with hydrofluoric acid. The hafnium oxide/graphene/PMMA film was rinsed with deionized water and isopropanol three times, respectively, which was then located on the molecule heterojunction to obtain a single molecule field effect transistor device with a top gate structure based on compound 2.

Example 22: Preparation of Compound 2 Based Single Molecule Field Effect Transistor

[0229] Example 22 differs from Example 21 in that: a zirconium oxide layer with a thickness of 5 nm prepared by the electron beam evaporation method was used as the dielectric layer.

Example 23: Preparation of Compound 2 Based Single Molecule Field Effect Transistor

[0230] Example 23 differs from Example 21 in that: a titanium oxide layer with a thickness of 5 nm prepared by the atomic layer deposition method was used as the dielectric layer.

Performance Test Example of Single Molecule Field Effect Transistor

Example 24

[0231] Agilent 4155C semiconductor tester and Karl Suss (PM5) manual probe station were used to test the performance of single molecule field effect transistors prepared in Examples 1-7.

[0232] At room temperature and atmospheric conditions, the gate voltage is changed within the range of 2 V to +2 V. The source-drain bias voltage (1 V+1 V) was applied with fixing a certain gate voltage. I-V characteristic curve of the above-mentioned single molecule field effect transistor modulated by the gate voltage was determined (as shown in FIGS. 3-9). It can be seen from FIGS. 3-9 that the single molecule field effect transistor prepared in Examples 1-7 exhibits the conductivity characteristic that it varies with the gate voltage. Specifically, the I-V curves under different gate voltages are significantly different. As the gate voltage changes from negative to positive, the conductivity characteristics significantly change by gradually decreasing. This indicates that the single molecular field effect transistors prepared in Examples 1-7 have efficient gate modulation characteristics. At the same time, it is fully proved that the single molecule field effect transistors provided by the present application have indeed realized the characteristics of industrial transistors and have a wide range of application prospects.

[0233] In addition, it should be noted that although the gate voltage range of the aforementioned test is 2 V+2 V, it is confirmed by experiments that I-V characteristic curves similar to those shown in FIGS. 3-9 can be obtained within the gate voltage range of 4 V+4 V, by which the conductivity characteristic that it varies with the gate voltage is also shown.

[0234] It should be noted that the single molecule field effect transistors prepared in Examples 8-23 can also fit I-V characteristic curves similar to those of the single molecule field effect transistor prepared in Example 1-7. Therefore, they can achieve the same technical effect of the single molecule field effect transistors prepared in Example 1-7.

[0235] Through the performance test experiment analysis, it can be seen that the strongly-polarized molecules containing the groups with the polarizability greater than 2 C.Math.m.sup.2/V are prone to polarization due to the abundant electron cloud of the molecules and the application of voltage, which in turn makes molecular orbital energy levels shift more. Therefore, it is easier to effectively realize the gate modulation of the single molecule field effect transistor.

[0236] It should be noted that the documents cited herein are incorporated herein by reference in their entirety, which will not be repeated herein.

[0237] The above examples are intended to illustrate the substantial content of the present application, but do not limit the scope of protection of the present application. A person skilled in the art should understand that the technical solutions of the present application may be modified or equivalently altered, without departing from the spirit and scope of the technical solutions of the present application.