Organic compounds, light modulating composition and light modulating devices employing the same
10007164 ยท 2018-06-26
Assignee
Inventors
Cpc classification
C07D209/50
CHEMISTRY; METALLURGY
C07C233/43
CHEMISTRY; METALLURGY
C09K2211/1029
CHEMISTRY; METALLURGY
C09K2211/1014
CHEMISTRY; METALLURGY
International classification
C07C233/43
CHEMISTRY; METALLURGY
C07C233/62
CHEMISTRY; METALLURGY
C07D209/50
CHEMISTRY; METALLURGY
Abstract
An organic compound, a light modulating composition and a light modulating device are provided. The organic compound has a chemical structure represented by formula (I):
XArX(I) wherein X is ##STR00001##
Ar is ##STR00002##
The organic compound is transparent in its neutral state. The amide group or imide group introduced into the aromatic amine not only enhances the solubility of the organic compound in the solvent, but also enhances the electrochemical stability of the organic compound.
Claims
1. An organic compound, having a structure as defined by Formula (I):
XArX(I) wherein X is ##STR00027## R.sup.1 is an isopropyl or cyclohexyl, R.sup.3 is H, an alkyl, or an alkoxy, R.sup.4 is H, or C1-8 alkyl group, Ar is ##STR00028## Ar is ##STR00029## Ar is ##STR00030## Ar.sup.3 is ##STR00031## and R.sup.2 is an alkyl or an alkoxy.
2. The organic compound as claimed in claim 1, wherein R.sup.2 is a C1-8 alkyl group or a C1-8 alkoxy group.
3. The organic compound as claimed in claim 1, wherein R.sup.3 is hydrogen, a C1-8 alkyl group, or a C1-8 alkoxy group.
4. The organic compound as claimed in claim 1, wherein the compound is represented by the following formula: ##STR00032## wherein R.sup.5 is isopropyl or cyclohexyl.
5. The organic compound as claimed in claim 1, wherein the compound is represented by the following formula: ##STR00033## wherein R.sup.4 is a C1-8 alkyl group.
6. The organic compound as claimed in claim 1, wherein the compound is represented by the following formula: ##STR00034## wherein R.sup.6 is isopropyl or cyclohexyl.
7. The organic compound as claimed in claim 1, wherein the compound is represented by the following formula: ##STR00035## wherein R.sup.4 is a C1-8 alkyl group.
8. A light modulating composition, comprising: a first oxidizable compound, wherein the first oxidizable compound is as claimed in claim 1; a reducible compound; an electrolyte; and a solvent.
9. The light modulating composition as claimed in claim 8, wherein the electrolyte is an organic ammonium salt or an inorganic lithium salt.
10. The light modulating composition as claimed in claim 8, wherein the oxidizable compound and the electrolyte have a mole ratio of 1:1 to 1:20, and the reducible compound and the electrolyte have a mole ratio of 1:1 to 1:20.
11. The light modulating composition as claimed in claim 8, wherein the concentration of the electrolyte is between 0.01M and 1.5M.
12. The light modulating composition as claimed in claim 8, wherein the reducible compound is selected from the group consisting of ##STR00036## wherein R.sup.7 is a C1-C10 alkyl group.
13. The light modulating composition as claimed in claim 9, further comprising a second oxidizable compound selected from the group consisting of ##STR00037## wherein R.sup.8 is H or an alkyl.
14. A light modulating device, comprising: a pair of electrodes, comprising: a first transparent substrate with a first transparent conductive layer on a surface of the transparent substrate; and a second transparent substrate with a second transparent conductive layer on a surface of the transparent substrate, disposed by arranging the first transparent conductive layer and the second transparent conductive layer to face each other; an isolating unit, inserted between the first and second transparent conductive layers to form a cell; and a light modulating composition filled in the cell, wherein the light modulating composition comprises: a first oxidizable compound, wherein the first oxidizable compound is as claimed in claim 1; a reducible compound; an electrolyte; and a solvent.
15. The light modulating device as claimed in claim 14, wherein the oxidizable compound is represented by the following formula: ##STR00038## wherein R.sup.5 is an isopropyl or cyclohexyl.
16. The light modulating device as claimed in claim 14, wherein the oxidizable compound is represented by the following formula: ##STR00039## wherein R.sup.4 is a C1-8 alkyl group.
17. The light modulating device as claimed in claim 14, wherein the oxidizable compound is represented by the following formula: ##STR00040## wherein R.sup.6 is an isopropyl or cyclohexyl.
18. The light modulating device as claimed in claim 14, wherein the oxidizable compound is represented by the following formula: ##STR00041## wherein R.sup.4 is a C1-8 alkyl group.
19. The light modulating device as claimed in claim 14, further comprising a second oxidizable compound, wherein the second oxidizable compound is selected from the group consisting of ##STR00042## wherein R.sup.5 is H or an alkyl.
20. The light modulating device as claimed in claim 14, wherein the distance from the first transparent conductive layer to the second transparent conductive layer is between 10 m to 200 m.
Description
BRIEF DESCRIPTION OF THE DRAWINGS
(1) The disclosure can be more fully understood by reading the subsequent detailed description and examples with references made to the accompanying drawings, wherein:
(2)
(3)
(4)
(5)
(6)
(7)
(8)
(9)
DETAILED DESCRIPTION
(10) In accordance with some embodiments of the disclosure, an organic compound is provided. The organic compound has a chemical structure represented by formula (I):
XArX(I)
wherein X can be
(11) ##STR00008##
R.sup.1 can be an alkyl, R.sup.3 can be H, an alkyl, or an alkoxy, R.sup.4 can be H, or methyl; Ar can be
(12) ##STR00009##
Ar is
(13) ##STR00010##
Ar is
(14) ##STR00011##
Ar.sup.3 is
(15) ##STR00012##
and R.sup.2 can be H, an alkyl, or an alkoxy.
(16) In one embodiment, R.sup.1 can be a C1-8 alkyl group.
(17) In one embodiment, R.sup.1 can be a C1-4 alkyl group.
(18) In one embodiment, R.sup.2 can be hydrogen, a C1-8 alkyl group, or a C1-8 alkoxy group.
(19) In one embodiment, R.sup.2 can be a C1-4 alkyl group, or a C1-4 alkoxy group.
(20) In one embodiment, R.sup.3 can be hydrogen, a C1-8 alkyl group, or a C1-8 alkoxy group.
(21) In one embodiment, R.sup.3 can be a C1-4 alkyl group, or a C1-4 alkoxy group.
(22) The organic compounds can be prepared from the reaction of carboxylic acids with diamine. The intermediate product of the diamine, dinitro can be prepared according to literature methods and then the diamine can be obtained from the dinitro through reduction as shown in Formula 2 or 3 below (J. Polym. Sci. Part A: Polym. Chem. 2006, 44, pp 4579-4592, the entire disclosure of which is incorporated herein by reference). Ar, Ar, and R2 in Formulas 2 and 3 have the same meaning as defined in the above Formula (1). The aforementioned organic compounds are applicable as an electrochromic element, a semiconductor, a solar cell, an organic electroluminescent element, an active substance of a non-linear material, etc.
(23) ##STR00013## ##STR00014##
(24) In accordance with some embodiments of the disclosure, the disclosure also provides an organic compound having a structure represented by the following formula:
(25) ##STR00015##
wherein R.sup.5 can be a C1-8 alkyl group.
(26) In accordance with some embodiments of the disclosure, the disclosure also provides an organic compound having a structure represented by the following formula:
(27) ##STR00016##
wherein R.sup.4 can be a C1-8 alkyl group.
(28) In accordance with some embodiments of the disclosure, the disclosure also provides an organic compound having a structure represented by the following formula:
(29) ##STR00017##
wherein R.sup.6 can be a C1-8 alkyl group.
(30) In accordance with some embodiments of the disclosure, the disclosure also provides an organic compound having a structure represented by the following formula:
(31) ##STR00018##
wherein R.sup.4 can be a C1-8 alkyl group.
(32) According to an embodiment of the disclosure, the aforementioned organic compound can be used as a first oxidizable compound which can be combined with a reducible compound, an electrolyte and a solvent to form a light modulating composition. In one embodiment, the oxidizable compound and the electrolyte have a molar ratio of 1:1 to 1:20, and the reducible compound and the electrolyte have a molar ratio of 1:1 to 1:20.
(33) In some embodiments, the electrolyte may contain at least one inert conducting salt. Examples of suitable inert conducting salts include lithium salts, sodium salts and tetraalkylammonium salts, such as tetrabutylammonium. Suitable solvents include solvents which are redox-inert at the voltages selected and which cannot dissociate to form electrophiles or nucleophiles or themselves react as sufficiently strong electrophiles or nucleophiles and thus could react with the colored ionic free radicals. Examples of suitable solvents include propylene carbonate (PC), gamma-Butyrolactone (GBL, -butyrolactone), acetonitrile, propionitrile, glutaronitrile, methylglutaronitrile, 3,3-oxydipropionitrile, hydroxypropionitrile, dimethylformamide, N-methylpyrrolidone, sulfolane, 3-methylsulfolane or mixtures thereof. The concentration of the electrolyte can be between 0.01M and 1.5M.
(34) In some embodiments, the reducible compound can be selected from the group consisting of
(35) ##STR00019##
wherein R.sup.7 is a C1-C10 alkyl group.
(36) In some embodiments of the disclosure, the oxidizable compound can include a second oxidizable compound, which can be
(37) ##STR00020##
or the combinations thereof, wherein R.sup.8 is H or an alkyl group.
(38) In accordance with some embodiments of the disclosure, a light modulating device can be provided. As shown in
(39) In some embodiments of the disclosure, the transparent substrates can be made of glass or plastic such as polycarbonate. The conductive layer can be made of indium tin oxide (ITO), antimony- or fluorine-doped tin oxide, antimony- or aluminum-doped zinc oxide, tin oxide or conductive organic polymers such as, for example, optionally substituted polythienyls, polypyrroles, polyanilines, polyacetylene.
(40) In some embodiments of the disclosure, the isolating unit can be formed by blending spacer elements with a thermosetting or photochemically curable adhesive. Spacer elements can be small spherules of plastic or glass or certain sand fractions
(41) In some embodiments of the disclosure, the distance from the first conducting material layer to the second conducting material layer can be between 10 m to 200 m.
(42) The light modulating device will change from colorless to a specific color (e.g. yellow green, sky blue, blue, deep blue, or deep purple) after being applied with a suitable voltage. The specific color and the voltage depend on the chemical structure of the organic oxidizable compound of the light modulating composition. After the voltage is switched off, the cell contents completely bleach once more within 1 min. The experiments described below show that the cell still worked satisfactorily after operating 10,000 coloring/bleaching cycles. In other words, the light modulating composition solution has good stability.
(43) Below, exemplary embodiments will be described in detail with reference to the accompanying drawings so as to be easily realized by a person having ordinary knowledge in the art. The inventive concept may be embodied in various forms without being limited to the exemplary embodiments set forth herein. Descriptions of well-known parts are omitted for clarity, and like reference numerals refer to like elements throughout.
EXAMPLES
(44) In the following Examples, the electrochemical analysis was performed by CH Instruments 612C to scan potentials of the thin film. The cyclic voltammetry (CV) was performed by a three-electrode system, wherein the ITO glass served as a working electrode (the coated polymer had an area of about 2.0 cm0.8 cm), an Ag/AgCl electrode (in saturated KCl solution) served as a reference electrode, a platinum wire served as an auxiliary electrode, 0.1M of tetrabutylammonium perchloride solution (in acetonitrile) served as an electrolyte, and a scan rate was 50 mV/s. The average value of a redox potential was defined as a half-wave potential.
Example A1: Preparation of Organic Compound (A1)
(45) 10.0 g of 4-methoxytriphenylamine-based diamine (compound (I)) and 6.4 g of isobutyric acid (compound (II)) were mixed in a reaction flask. 25 ml of Dimethylacetamide (DMAc) serving as a solvent was added into the reaction flask, and 20.3 g of Triphenyl Phosphate (TPP) and 5.68 g of pyridine serving as a catalyst were then added into the reaction flask. The mixture in the reaction flask was heated to 105 C. for 4 hours, and then cooled down to room temperature. The cooled reaction mixture was poured into ethanol to precipitate a solid, and then filtered to collect the solid. The solid was washed by water and then dried, a compound (A1) (white solid) was obtained. The synthesis pathway of the above reaction was as follows:
(46) ##STR00021##
(47) The physical measurement of the compound (A1) is listed below: 1H NMR (500 MHz, DMSO-d.sup.6): 1.02 (d, J=7.0 Hz, 6H), 2.49 (m, 2H), 3.66 (s, 3H), 6.78 (d, J=9.0 Hz, 4H), 6.81 (d, J=8.5 Hz, 2H), 6.87 (d, J=8.5 Hz, 2H), 7.41 (d, J=9.0 Hz, 4H), 9.65 (s, 2H). 13C NMR (125 MHz, DMSO-d6): 19.5, 34.8, 55.2, 114.8, 120.4, 122.9, 125.7, 133.9, 140.5, 143.0, 155.2, 174.8. Anal. calcd for C.sub.27H.sub.31N.sub.3O.sub.3: C, 72.78; H, 7.01; N, 9.43; found: C, 72.69; H, 7.03; N, 9.51.
(48) The compound (A1) has a cyclic voltammetry CV diagram as shown in
Example A2: Preparation of Organic Compound (A2)
(49) 10.0 g of 4-methoxytriphenylamine-based diamine (compound (I)) and 8.4 g of cyclohexanoic acid (compound (III)) were mixed in a reaction flask. 25 ml of Dimethylacetamide (DMAc) serving as a solvent was added into the reaction flask, and 20.3 g of Triphenyl Phosphate (TPP) and 5.68 g of pyridine serving as a catalyst were then added into the reaction flask. The mixture in the reaction flask was heated to 105 C. for 4 hours, and then cooled down to room temperature. The cooled reaction mixture was poured into ethanol to precipitate a solid, and then filtered to collect the solid. The solid was washed by water and then dried, a compound (A2) (white solid) was obtained. The synthesis pathway of the above reaction was as follows:
(50) ##STR00022##
(51) The physical measurement of the compound (A2) is listed below: 1H NMR (500 MHz, DMSO-d.sup.6) 1.13-1.44 (m, 10H), 1.63-1.79 (m, 10H), 2.29 (t, 2H), 3.72 (s, 3H), 6.84 (d, J=9.0 Hz, 4H), 6.88 (d, J=8.5 Hz, 2H), 6.95 (d, J=8.5 Hz, 2H), 7.48 (d, J=9.0 Hz, 4H), 9.67 (s, 2H). 13C NMR (125 MHz, DMSO-d.sup.6): 13.9, 22.0, 25.1, 28.5, 28.6, 31.2, 55.2, 114.8, 120.2, 122.8, 125.8, 140.5, 143.0, 155.24, 170.8. Anal. calcd for C.sub.33H.sub.39N.sub.3O.sub.3: C, 75.4; H, 7.48; N, 7.99; found C, 74.8; H, 7.45; N, 7.87.
(52) The compound (A2) has redox potential as tabulated in Table 1 below, transmittance of neutral and oxidation state at different wavelengths as tabulated in Table 2 below.
Example A3: Preparation of Organic Compound (A3)
(53) 10.0 g of 4-methoxytriphenylamine-based diamine (compound (I)) and 9.45 g of octanoic acid (compound (IV)) were mixed in a reaction flask. 25 ml of Dimethylacetamide (DMAc) serving as a solvent was added into the reaction flask, and 20.3 g of Triphenyl Phosphate (TPP) and 5.68 g of pyridine serving as a catalyst were then added into the reaction flask. The mixture in the reaction flask was heated to 105 C. for 4 hours, and then cooled down to room temperature. The cooled reaction mixture was poured into ethanol to precipitate a solid, and then filtered to collect the solid. The solid was washed by water and then dried, a compound (A3) (white solid) was obtained. The synthesis pathway of the above reaction was as follows:
(54) ##STR00023##
(55) The physical measurement of the compound (A3) is listed below: 1H NMR (500 MHz, DMSO-d.sup.6): 0.86 (t, 6H), 1.26-1.59 (m, 16H), 2.51 (t, 4H), 3.73 (s, 3H), 6.85 (d, J=9.0 Hz, 4H), 6.88 (d, J=8.5 Hz, 2H), 6.95 (d, J=8.5 Hz, 2H), 7.47 (d, J=9.0 Hz, 4H), 9.76 (s, 2H). 13C NMR (125 MHz, DMSO-d.sup.6): 13.9, 22.0, 25.2, 28.5, 28.6, 31.2, 55.2, 114.8, 120.2, 122.8, 125.8, 133.8, 140.5, 143.0, 155.2, 170.8. Anal. calcd for C.sub.33H.sub.43N.sub.3O.sub.3: C, 74.82; H, 8.18; N, 7.93; found: C, 74.89; H, 8.09; N, 7.88.
(56) The compound (A3) has redox potential as tabulated in Table 1 below, the transmittance of neutral and oxidation state at different wavelengths as tabulated in Table 2 below.
Example A4: Preparation of Organic Compound (A4)
(57) [please add a paragraph number here] 10.0 g of 4-methoxypentaphenylamine-based diamine (compound (V)) and 5.1 g of cyclohexanoic acid (compound (III)) were mixed in a reaction flask. 25 ml of Dimethylacetamide (DMAc) serving as a solvent was added into the reaction flask, and 20.3 g of Triphenyl Phosphate (TPP) and 5.68 g of pyridine serving as a catalyst were then added into the reaction flask. The mixture in the reaction flask was heated to 105 C. for 4 hours, and then cooled down to room temperature. The cooled reaction mixture was poured into ethanol to precipitate a solid, and then filtered to collect the solid. The solid was washed by water and then dried, a compound (A4) (white solid) was obtained. The synthesis pathway of the above reaction was as follows:
(58) ##STR00024##
(59) The physical measurement of the compound (A4) is listed below: 1H NMR (500 MHz, DMSO-d.sup.6) 1.24-1.38 (m, 10H), 1.40-1.75 (m, 10H), 1.77 (t, 2H), 3.72 (s, 6H), 6.79 (s, 4H), 6.87-6.88 (m, 6H), 6.97 (d, J=8.5 Hz, 2H), 7.47 (d, J=9.0 Hz, 4H), 9.69 (s, 2H). 13C NMR (125 MHz, DMSO-d.sup.6) 25.2, 25.4, 29.1, 44.7, 55.2, 114.8, 120.3, 123.0, 123.2, 125.9, 134.0, 140.4, 142.0, 142.9, 155.3, 173.8. Anal. calcd for C.sub.46H.sub.52N.sub.4O.sub.4: C, 76.21; H, 7.23; N, 7.73; found C, 75.95; H, 7.29; N, 7.75.
(60) The compound (A4) has a cyclic voltammetry CV diagram as shown in
Example B1: Preparation of Organic Compound (B1)
(61) 1.50 g of 4-methoxytriphenylamine-based diamine (compound (I)) and 1.70 g of hexahydrophthalic anhydride (compound (VI)) were mixed in a reaction flask. 2.5 ml of Dimethylacetamide (DMAc) serving as a solvent was added into the reaction flask, and a little of Isoquinoline serving as a catalyst was then added into the reaction flask. The mixture in the reaction flask was heated to 210 C. for 5 hours, and then cooled down to room temperature. The cooled reaction mixture was diluted by methanol and poured into water to precipitate a solid, and then filtered to collect the solid. The solid was washed by water and then dried, a compound (B1) (beige solid) was obtained. The synthesis pathway of the above reaction was as follows:
(62) ##STR00025##
(63) The physical measurement of the compound (B1) is listed below: 1H NMR (500 MHz, DMSO-d.sup.6) 1.38 (m, 4H), 1.73 (q, 4H), 3.08 (q, 2H), 3.75 (s, 3H), 6.97 (d, J=9.5 Hz, 2H), 7.02 (d, J=9.0 Hz, 4H), 7.11 (d, J=9.5 Hz, 2H), 7.14 (d, J=9.0 Hz, 4H). 13C NMR (125 MHz, DMSO-d6): 21.4, 23.4, 55.3, 115.4, 122.0, 126.2, 127.9, 128.1, 139.1, 147.0, 156.7, 178.8. Anal. calcd for C.sub.35H.sub.35N.sub.3O.sub.5: C, 72.77; H, 6.11; N, 7.27; found C, 72.35; H, 6.16; N, 7.25.
(64) The compound (B1) has a cyclic voltammetry CV diagram as shown in
Example B2: Preparation of Organic Compound (B2)
(65) 5.0 g of 4-methoxypentaphenylamine-based diamine (compound (V)) and 3.06 g of hexahydrophthalic anhydride (compound (VI)) were mixed in a reaction flask. 7.5 ml of dimethylacetamide (DMAc) serving as a solvent was added into the reaction flask, and a little of isoquinoline serving as a catalyst was then added into the reaction flask. The mixture in the reaction flask was heated to 210 C. for 5 hours, and then cooled to room temperature. The cooled reaction mixture was diluted by methanol and poured into water to precipitate a solid, and then filtered to collect the solid. The solid was washed by water and then dried, a compound (B2) (beige solid) was obtained. The synthesis pathway of the above reaction was as follows:
(66) ##STR00026##
(67) The physical measurement of the compound (B2) is listed below: 1H NMR (500 MHz, DMSO-d.sup.6) 1.361.42 (m, 8H), 1.702.00 (m, 8H), 3.08 (t, 4H), 3.74 (s, 6H), 6.927.10 (m, 20H). 13C NMR (125 MHz, DMSO-d.sup.6): 21.3, 21.4, 23.3, 55.2, 115.2, 120.2, 124.9, 125.0, 127.5, 127.7, 139.4, 142.2, 147.6, 156.3, 178.8. Anal. calcd for C.sub.48H.sub.46N.sub.4O.sub.6: C, 74.40; H, 5.98; N, 7.23; found C, 74.21; H, 6.03; N, 7.27.
(68) The compound (B2) has a cyclic voltammetry CV diagram as shown in
(69) TABLE-US-00001 TABLE 1 Example E1.sub.1/2 (V).sup.a E2.sub.1/2 (V).sup.b A1 0.68 (teal) A2 0.67 (teal) A3 0.68 (teal) A4 0.46 (green) 0.81 (blue) B1 0.93 B2 0.60 (green) 0.94 (blue) .sup.aE1.sub.1/2 (V) is a half-wave potential at the first oxidation state. .sup.bE2.sub.1/2 (V) is a half-wave potential at the second oxidation state.
(70) Table 1, Table 2 and
(71) TABLE-US-00002 TABLE 2 Transmittance (%) 450 600 700 800 900 1000 Example/T(%) nm nm nm nm nm nm neutral state of A1 78.5 78.5 78.1 72.7 63.8 49.7 oxidation state of A1 74.5 67.5 50.2 36.1 62.5 49.7 neutral state of A2 79.8 78.7 78.1 72.6 63.6 49.2 oxidation state of A2 60.9 55.1 33.9 17.6 57.3 45.1 neutral state of A3 78.4 77.8 77.1 71.4 62.3 47.6 oxidation state of A3 66.2 61.0 40.9 19.3 60.5 49.0 neutral state of B1 78.6 78.2 77.6 71.9 62.8 47.7 oxidation state of B1 53.9 54.1 38.6 57.4 59.9 46.7 neutral state of A4 74.3 75.8 74.9 69.2 60.1 45.5 oxidation state of A4 13.1 26.8 38.8 24.5 9.08 4.65 neutral state of B2 76.7 77.0 76.6 71.2 61.3 46.4 oxidation state of B2 6.98 20.3 19.2 6.73 1.81 1.51 neutral state of PSN.sup.c 79.0 78.0 77.3 71.3 61.9 47.1 oxidation state of PSN 34.7 37.1 54.2 67.7 60.4 46.5 .sup.CPSN is phenothiazine as a comparative compound
(72) Table 2, 3 and
Example C1: Preparation of a Light Modulating Device
(73) Tetrabutyl ammonium tetrafluoroborate (TBABF.sub.4) was dissolved in propylene carbonate (PC) to form a 0.5 M solution. Next, compound A2 and viologen [(HV(BF.sub.4).sub.2] was dissolved in the above solution to form a light modulating composition solution, wherein the concentration of compound A2 was 0.1M and the concentration of viologen was 0.05M. Two ITO conductive glass plates were cut to the desired size and the ITO layers of the plates face each other. An isolating unit was connected with the two ITO conductive glass plates to construct a cell. Via a port on the isolating unit, the aforementioned light modulating composition is introduced into the cell so that the cell was filled with the light modulating composition solution. The port was sealed so that the light modulating device is formed. The distance between the glass plates was about 50 m. The light modulating device was applied a voltage of 1.4V to measure the transmittance of the device as tabulated in Table 3 below.
Example C2: Preparation of a Light Modulating Device
(74) Tetrabutyl ammonium tetrafluoroborate (TBABF.sub.4) was dissolved in propylene carbonate (PC) to form a 0.5 M solution. Next, compound B1 and viologen [(HV(BF.sub.4).sub.2] were dissolved in the above solution to form a light modulating composition solution, wherein the concentration of compound B1 was 0.1M and the concentration of viologen was 0.05M. Two ITO conductive glass plates were cut to the desired size and the ITO layers of the plates face each other. An isolating unit was connected with the two ITO conductive glass plates to construct a cell. Via a port on the isolating unit, the aforementioned light modulating composition is introduced into the cell so that the cell was filled with the light modulating composition solution. The port was sealed so that the light modulating device is formed. The distance between the glass plates was about 50 m. The light modulating device was applied a voltage of 1.6V to measure the transmittance of the device as tabulated in Table 3 below. The transmission spectrum of the neutral state (off-state) and oxidation state (on-state) of the device obtained as shown in
Example C3: Preparation of a Light Modulating Device
(75) Tetrabutyl ammonium tetrafluoroborate (TBABF4) was dissolved in propylene carbonate (PC) to form a 0.5 M solution. Next, compound A4 and viologen [(HV(BF4)2] was dissolved in the above solution to form a light modulating composition solution, wherein the concentration of compound A4 was 0.1M and the concentration of viologen was 0.05M. Two ITO conductive glass plates were cut to the desired size and the ITO layers of the plates face each other. An isolating unit was connected with the two ITO conductive glass plates to construct a cell. Via a port on the isolating unit, the aforementioned light modulating composition is introduced into the cell so that the cell was filled with the light modulating composition solution. The port was sealed so that the light modulating device is formed. The distance between the glass plates was about 50 m. The light modulating device was applied a voltage of 1.1V to measure the transmittance of the device as tabulated in Table 3 below.
Example C4: Preparation of a Light Modulating Device
(76) Tetrabutyl ammonium tetrafluoroborate (TBABF4) was dissolved in propylene carbonate (PC) to form a 0.5 M solution. Next, compound B2 and viologen [(HV(BF4)2] was dissolved in the above solution to form a light modulating composition solution, wherein the concentration of compound B2 was 0.1M and the concentration of viologen was 0.05M. Two ITO conductive glass plates were cut to the desired size and the ITO layers of the plates face each other. An isolating unit was connected with the two ITO conductive glass plates to construct a cell. Via a port on the isolating unit, the aforementioned light modulating composition is introduced into the cell so that the cell was filled with the light modulating composition solution. The port was sealed so that the light modulating device is formed. The distance between the glass plates was about 50 m. The light modulating device was applied a voltage of 1.3V to measure the transmittance of the device as tabulated in Table 3 below.
(77) TABLE-US-00003 TABLE 3 Oper- ating volt- Transmittance (%) age 450 600 700 800 900 1000 Device (V) nm nm nm nm nm nm neutral state of C1 0.00 76.1 76.4 76.4 71.7 63.6 50.8 oxidation state of C1 1.30 46.6 2.65 1.66 0.15 41.9 38.8 neutral state of C2 0.00 78.1 78.0 77.2 71.5 62.4 47.8 oxidation state of C2 1.60 51.8 4.60 3.79 0.57 4.76 42.5 neutral state of C3 0.00 77.2 76.4 76.1 70.7 61.9 48.0 oxidation state of C3 1.10 8.00 2.46 23.4 18.9 4.70 1.84 neutral state of C4 0.00 74.4 76.0 75.5 69.9 60.7 46.3 oxidation state of C4 1.30 16.4 7.56 26.9 13.6 4.21 2.99 neutral state of PSN 0.00 78.1 76.4 76.5 71.2 62.2 47.6 oxidation state of 1.30 29.2 7.72 38.0 53.2 49.1 41.9 PSN
(78) Table 3 and
Example D: Preparation of a Light Modulating Device
(79) Tetrabutyl ammonium tetrafluoroborate (TBABF.sub.4) was dissolved in propylene carbonate (PC) to form a 0.5 M solution. Next, compound A1 and viologen [(HV(BF.sub.4).sub.2] was dissolved in the above solution to form a light modulating composition solution, wherein the concentration of compound A1 was 0.1M and the concentration of viologen was 0.05M. Two ITO conductive glass plates were cut to the desired size and the ITO layers of the plates face each other. An isolating unit was connected with the two ITO conductive glass plates to construct a cell. Via a port on the isolating unit, the aforementioned light modulating composition is introduced into the cell so that the cell was filled with the light modulating composition solution. The port was sealed so that the light modulating device is formed. The distance between the glass plates was about 50 m.
(80) The light modulating device was applied a voltage of 1.3V for 3.250 seconds (on-state), and was applied a voltage of 1.3V for 0.375 seconds (off-state), and then stay at 0V for 3.675 seconds. Repeating the above method, the device was subjected to a cycle life test. As shown in the transmission spectrum of
(81) TABLE-US-00004 TABLE 4 Transmittance(%) 400 500 625 770 800 900 Switching state nm nm nm nm nm nm Original neutral 68.8 83.0 77.6 73.7 71.6 62.8 state 1st After first on 0.24 46.2 11.2 2.21 6.28 54.2 After 11001st on 0.31 46.9 11.7 1.80 5.43 55.5 After 11000st off 66.0 81.1 76.9 73.7 71.7 63.0
Example E: Preparation of a Transparent-Green Complementary Light Modulating Device
(82) Tetrabutyl ammonium tetrafluoroborate (TBABF.sub.4) was dissolved in propylene carbonate (PC) to form a 0.5 M solution. Next, compound A1, 5,10-dimethylphenazine (DMP) and viologen [(HV(BF.sub.4).sub.2] were dissolved in the above solution to form a light modulating composition solution, wherein the concentration of compound A1 was 0.025M, the concentration of DMP was 0.025M and the concentration of viologen was 0.05M. Two ITO conductive glass plates were cut to the desired size and the ITO layers of the plates face each other. An isolating unit was connected with the two ITO conductive glass plates to construct a cell. Via a port on the isolating unit, the aforementioned light modulating composition is introduced into the cell so that the cell was filled with the light modulating composition solution. The port was sealed so that the light modulating device is formed. The distance between the glass plates was about 50 m.
(83) When the light modulating device was applied a voltage ad the spectrum shows that transmission of the device reduced to 10.4% at a wavelength of 450 nm. The device turned from transparent at neutral state to deep green (oxidation state). Moreover, after switching off the voltage the device can be recovered to transparent (off-state) in 1 second.
Example F: Preparation of a Transparent-Deep Blue Complementary Light Modulating Device
(84) Tetrabutyl ammonium tetrafluoroborate (TBABF.sub.4) was dissolved in propylene carbonate (PC) to form a 0.5 M solution. Next, compound A1, phenothiazine (PSN), methylphenothiazine (MePSN) and viologen [(HV(BF.sub.4).sub.2] were dissolved in the above solution to form a light modulating composition solution, wherein the concentration of compound A1 was 0.05M, the concentration of PSN was 0.05M, the concentration of MePSN was 0.05M and the concentration of viologen was 0.05M. Two ITO conductive glass plates were cut to the desired size and the ITO layers of the plates face each other. An isolating unit was connected with the two ITO conductive glass plates to construct a cell. Via a port on the isolating unit, the aforementioned light modulating composition is introduced into the cell so that the cell was filled with the light modulating composition solution. The port was sealed so that the light modulating device is formed. The distance between the glass plates was about 50 m.
(85) When the light modulating device was applied a voltage gradually to 1.3V, the spectrum shows that transmission of the device reduced to 10.4% at a wavelength of 450 nm. The device turned from transparent at neutral state to deep green (oxidation state). Moreover, After switching off the voltage the device can be recovered to transparent (off-state) in 1 second.
Example G: Preparation of a Transparent-Dark Complementary Light Modulating Device
(86) Tetrabutyl ammonium tetrafluoroborate (TBABF.sub.4) was dissolved in propylene carbonate (PC) to form a 0.5 M solution. Next, compound A1, phenothiazine (PSN), methylphenothiazine (MePSN) and viologen [(HV(BF.sub.4).sub.2] were dissolved in the above solution to form a light modulating composition solution, wherein the concentration of compound A1 was 0.1M, the concentration of PSN was 0.1M, the concentration of MePSN was 0.1M and the concentration of viologen was 0.1M. Two ITO conductive glass plates were cut to the desired size and the ITO layers of the plates face each other. An isolating unit was connected with the two ITO conductive glass plates to construct a cell. Via a port on the isolating unit, the aforementioned light modulating composition is introduced into the cell so that the cell was filled with the light modulating composition solution. The port was sealed so that the light modulating device is formed. The distance between the glass plates was about 50 m.
(87) When the light modulating device was applied a voltage gradually to 1.3V, the spectrum shows that transmission of the device reduced to 10.4% at a wavelength of 450 nm. The device turned from transparent at neutral state to deep green (oxidation state). The transmission spectrum of the device at different wavelengths and at different state was obtained and as shown in
Comparative Example H: Preparation of a Light Modulating Device
(88) Tetrabutyl ammonium tetrafluoroborate (TBABF.sub.4) was dissolved in propylene carbonate (PC) to form a 0.5 M solution. Next, phenothiazine (PSN) and viologen [(HV(BF.sub.4).sub.2] was dissolved in the above solution to form a light modulating composition solution, wherein the concentration of PSN was 0.1M and the concentration of viologen was 0.05M. Two ITO conductive glass plates were cut to the desired size and the ITO layers of the plates face each other. An isolating unit was connected with the two ITO conductive glass plates to construct a cell. Via a port on the isolating unit, the aforementioned light modulating composition is introduced into the cell so that the cell was filled with the light modulating composition solution. The port was sealed so that the light modulating device is formed. The distance between the glass plates was about 50 m. The transmittance spectrum of neutral and oxidation state was shown in
(89) When the light modulating device was applied a voltage gradually to 1.3V, the device turned from transparent at neutral state to deep blue (oxidation state). The transmission spectrum of the device at different wavelengths and at different state was obtained and as shown in
(90) It will be apparent to those skilled in the art that various modifications and variations can be made to the disclosed embodiments. It is intended that the specification and examples be considered as exemplary only, with the true scope of the disclosure being indicated by the following claims and their equivalents.