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Bithiazole derivates and use thereof

A technology for bibithiazole and derivatives, applied in the field of bibithiazole derivatives, can solve the problems of complicated preparation process, high price of ruthenium, etc., and achieve the effects of easy preparation, cost reduction and low cost

Inactive Publication Date: 2011-02-23
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The photosensitizing dye with the best photoelectric conversion efficiency so far is bipyridyl ruthenium complex (about 11.5%), but because ruthenium is a rare metal, the price is more expensive, and its preparation process is more complicated

Method used

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  • Bithiazole derivates and use thereof
  • Bithiazole derivates and use thereof
  • Bithiazole derivates and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051]

[0052] With the teaching of the above preparation methods, those skilled in the art can prepare other compounds contained in formula I without creative efforts.

[0053] Application of the bidithiazole derivatives provided by the invention in the preparation of photosensitizers for dye-sensitized solar cells:

[0054] The preparation of the battery is firstly to pretreat the conductive glass, and then apply the titanium dioxide slurry on the treated conductive glass, after high temperature treatment, immerse in the dye bath and absorb for 12 hours to form the working electrode of the battery. A dye-sensitized solar cell was prepared by encapsulating the configured electrolyte between the working electrode and the platinum-coated counter electrode with a sealant. The test of battery performance is to lead wires from the working electrode and counter electrode of the battery respectively, and connect them to the battery performance testing device. The working area of...

Embodiment 2

[0080]

[0081] Add 150mg (0.19mmol) compound X-1, 5mL 2M K 2 CO 3 , 8mL THF, plus 22mg (0.019mmol) Pd (PPh 3 ) 4 , under the protection of argon, heat to reflux for 0.5h, inject 216mg (0.57mmol) of methoxytriphenylamine borate in THF and cyclohexane solution, heat to reflux overnight, stop heating, cool to room temperature, spin off THF, dichloro Methane was dissolved, washed with water, and the organic layer was anhydrous Na 2 SO 4 Drying, spin-drying, silica gel column chromatography, developing solvent is petroleum ether / dichloromethane=2 / 1 to 1 / 1 to 1 / 2 (V / V), obtains 200mg product (compound XI-2), yield 93 %.

[0082] 1 H NMR (CDCl 3 , 500MHz), δ: 9.91(s, 1H), 7.73(d, J=4.0Hz, 1H), 7.27(d, J=4.0Hz, 1H), 7.24(d, J=8.8Hz, 2H), 7.12 (d, J=8.8Hz, 4H), 6.93(d, J=8.8Hz, 2H), 6.87(d, J=8.8Hz, 4H), 3.81(s, 6H), 2.99(t, J=8.0Hz , 2H), 2.82(t, J=8.0Hz, 2H), 1.82-1.74(m, 4H), 1.43-1.26(m, 12H), 0.90-0.86(m, 6H).

[0083]

[0084] Add 150mg (0.20mmol) of compound XI-...

Embodiment 3

[0089]

[0090] Add 190mg (0.36mmol) compound X-1, 5mL 2MK 2 CO 3 , 8mLTHF, plus 42mg (0.036mmol) Pd (PPh 3 ) 4 , under argon protection, heat to reflux for 0.5h, inject 234mg (0.72mmol) of carbazole borate in THF and cyclohexane solution, heat to reflux overnight, stop heating, cool to room temperature, spin off THF, dichloromethane dissolves, Washed with water, the organic layer was anhydrous Na 2 SO 4 Drying, spin-drying, silica gel column chromatography, the developing solvent is petroleum ether / dichloromethane=2 / 1 to 1 / 1 (V / V), to obtain 250 mg of the product (Compound XI-3), the yield is 95%.

[0091] 1 H NMR (CDCl 3 , 500MHz), δ: 9.91(s, 1H), 8.18(s, 1H), 8.11(d, J=7.6Hz, 1H), 7.73(d, J=4.0Hz, 1H), 7.55(d, J= 8.4Hz, 1H), 7.51(t, J=7.6Hz, 1H), 7.44(t, J=8.1Hz, 2H), 7.27(m, 2H)., 4.32(t, J=7.2Hz, 2H), 3.01(t, J=7.8Hz, 2H), 2.90(t, J=7.6Hz, 2H), 1.94-1.88(m, 2H), 1.86-1.79(m, 4H), 1.44-1.25(m, 22H) , 0.91-0.84(m, 9H).

[0092]

[0093] Add 100 mg (0.14 mmol...

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Abstract

The invention relates to bithiazole derivates and use thereof. The bithiazole derivates are prepared by chemically modifying bithiazole (matrix) (which means connecting aromatic ring electrondonating radicals and nitrile acetic acid electron-withdrawing radicals). The electrons of the bithiazole derivates designed and prepared in the invention can be transferred more easily, so that the bithiazole derivates have the potentiality of effectively converting the optical energy into the electric energy. The bithiazole derivates can be used as a photosensitizer for dye-sensitized solar cells.

Description

technical field [0001] The present invention relates to a bithiazole derivative and its application. Background technique [0002] With the rapid development of human industrial civilization, mineral resources such as coal, oil and natural gas are increasingly depleted, and the resulting energy crisis and environmental pollution have become serious problems that need to be solved urgently. Therefore, people urgently need to find other new alternative energy sources. Dye-sensitized solar cells (B.O'Regan, M. , Nature, 1991, 353, 737-740), because of its low cost, it has potential practical value. [0003] Dye-sensitized solar cells (DSSCs) are usually composed of semiconductor oxide nanoporous membranes, dye sensitizers, redox electrolytes, and Pt electrodes, among which dye sensitizers with broad spectrum, high molar extinction coefficient, and low cost are the key components of the entire DSSC. core part of the system. So far, the photosensitive dye with the best photo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01M14/00H01L51/46C07D277/56H01G9/042H01G9/20C07D417/14
CPCY02E10/542H01L51/0061H01L51/0069Y02E10/549H10K85/636H10K85/656
Inventor 花建丽贺锦香武文俊姜义华曲大辉田禾
Owner EAST CHINA UNIV OF SCI & TECH