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Ethylene naphthalene and paradiazine dye and application thereof to dye-sensitized solar cells.

A technology of solar cells and dye sensitization, which can be used in different fields and can solve the problems of high cost and limited application

Inactive Publication Date: 2009-08-26
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently the most used is M. The N3 and N719 dyes invented by the professor's research group are ruthenium complex dyes. Due to the introduction of noble metals, the cost of such dyes is relatively high, which limits its application.

Method used

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  • Ethylene naphthalene and paradiazine dye and application thereof to dye-sensitized solar cells.
  • Ethylene naphthalene and paradiazine dye and application thereof to dye-sensitized solar cells.
  • Ethylene naphthalene and paradiazine dye and application thereof to dye-sensitized solar cells.

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Synthesis of 3-diphenylamine-8,9-dicarboxy-acenaphthopyrazine

[0030] (1) Synthesis of 5-bromoacenaphthylquinone:

[0031]

[0032] In a 500mL two-necked flask, add 20g (109.8mmol) of acenaphthylquinone and 25.0mL of liquid bromine (466.8mmol), start stirring, control the temperature in an oil bath at 6070°C, and reflux the reaction solution. After 2h, stop the reaction and add hydrogen sulfite Sodium aqueous solution until the reaction solution is colorless. After diluting with water, filter under reduced pressure, and wash with water for several times for beating until pH=7.0. The filter cake was recrystallized four times in glacial acetic acid to obtain 5-bromoacenaphthoquinone as brown-yellow needle-like crystals with a yield of 90%. NMR 1 H NMR (400MHz, DMSO-d 6 )δ8.39(d, 1H), 8.21(d, 1H), 8.15(d, 1H), 8.04(t, 1H), 7.96(d, 1H); HRMS-EI(70eV) m / z.

[0033] (2) Synthesis of 5-diphenylamine-acenaphthenequinone:

[0034]

[0035] The reaction is...

Embodiment 2

[0043] Example 2: Synthesis of 3-diphenylamine-8,9-dicarboxy-acenaphthopyrazine-acene

[0044] (1) Synthesis of 3-diphenylamine-8,9-dicyano-acenaphthopyrazine-acene

[0045]

[0046] Synthetic method is substantially the same as (3) in embodiment 1, nuclear magnetic 1 HNMR ((CDCl 3 )): δ7.12-7.16(m, 6H), 7.32(t, 4H), 7.46(d, 1H), 7.62(t, 1H), 7.86(d, 1H), 8.36(d, 1H), 8.42 (d, 1H), 8.60 (d, 2H).FAB MS: m / e 471 (M + ).

[0047] (2) Synthesis of 3-diphenylamine-8,9-dicarboxy-acenaphthopyrazine-acene

[0048]

[0049] Synthetic method is substantially the same as (4) in embodiment 1, nuclear magnetic 1 HNMR ((DMSO-d 6 )): δ7.09-7.14(m, 6H), 7.35(t, 4H), 7.44(d, 1H), 7.30(t, 1H), 7.80(d, 1H), 8.38-8.41(m, 4H) .MS API-ES: [M-H] + (508, M / Z).

Embodiment 3

[0050] Example 3: Synthesis of 3-diphenylamine-8-carboxy-acenaphthopyrazine and 3-diphenylamine-9-carboxy-acenaphthopyrazine

[0051] (1) Synthesis of 3-diphenylamine-8-cyano-acenaphthopyrazine and 3-diphenylamine-9-cyano-acenaphthopyrazine

[0052]

[0053] The synthetic method is basically the same as (3) in Example 1, and what this reaction obtains is 3-diphenylamine-8-cyano-acenaphthopyrazine and 3-diphenylamine-9-cyano-acenaphthopyrazine The isomers of acene, the isomers cannot be separated by silica gel column, and the isomers can not be separated by NMR 1 HNMR showed that the ratio of isomers was about 1:1. NMR 1 HNMR (CDCl 3 ): δ7.10-7.16(m, 6H), 7.28-7.32(m, 4H), 7.45-7.48(m, 1H), 7.59(t, 1H), 7.83(d, 1H), 7.86-7.90(m , 1H), 8.25-8.28(m, 1H), 8.34-8.39(m, 2H), 8.54(s, 1H).FAB MS: m / e 446(M + ).

[0054] (2) Synthesis of 3-diphenylamine-8-carboxy-acenaphthopyrazine and 3-diphenylamine-9-carboxy-acenaphthopyrazine

[0055]

[0056] The synthetic method is b...

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Abstract

The invention relates to the application field of photoelectric conversion materials in the fine chemistry industry, in particular to ethylene naphthalene and paradiazine dye and application thereof to dye-sensitized solar cells. The dye is characterized by taking ethylene naphthalene and paradiazine and derivatives thereof as a conjugated system, one end of the conjugated system is connected with adjacent dicarboxyl or a single carboxyl as electron withdraw group which is used to be absorbed on TiO2, and the other end thereof is connected with different electron-donating groups to form an electric push-pull type organic dye. As taking the ethylene naphthalene and paradiazine as the conjugated system ensures a fine plane structure, by connecting the conjugated system with the electron group and the electron-withdrawing group, electrons are easy to transfer in case of excited state and the dye is led to generate unique photoelectrochemical property, therefore enjoying fine application performance in dye-sensitized solar cells; in addition, the ethylene naphthalene and paradiazine dye features simple synthetic method and easily available raw materials, thus being capable of replacing noble metal photosensitive dyes with relatively high price and effectively reducing the cost of the dye-sensitized solar cells.

Description

Technical field [0001] The invention belongs to the application field of photoelectric conversion materials in fine chemicals, and specifically relates to a class of acenaphthopyrazine and its derivatives as a conjugated system, with one end connected to an ortho-dicarboxylic group or a single carboxyl group as an electron-withdrawing group for adsorption on TiO 2 On the other end, different electron-donating groups are connected to form a type of electron push-pull dye, and the application of the dye in dye-sensitized solar cells. Background technique [0002] Dye-sensitized solar cells were invented in 1991 by M. The professor proposed a new type of device for converting solar energy into electrical energy. Its composition is generally as follows: a photoanode composed of a nanoporous oxide film adsorbed with a photosensitive dye and a transparent conductive substrate. The Pt-coated conductive glass is a photocathode filled in the two electrodes. between the electrolyte ...

Claims

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Application Information

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IPC IPC(8): C09B57/00H01G9/20H01L51/42H01L51/46
CPCY02E10/542Y02E10/549
Inventor 崔京南孔志霞杨翠翠马廷丽周慧芝孙立成
Owner DALIAN UNIV OF TECH
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