Indoline-dithienoquinoxaline-dibenzo[a,c]phenazine dye and application of dye to dye-sensitized solar cell

A dye-sensitized, solar cell technology, applied in azine dyes, organic dyes, circuits, etc., to achieve the effects of good light absorption, promotion of electron transfer, and simple synthesis process

Active Publication Date: 2018-06-15
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No quinoxaline dyes with indoline as electron donor and dibenzo[a,c]phenazine as co-acceptor have been reported so far

Method used

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  • Indoline-dithienoquinoxaline-dibenzo[a,c]phenazine dye and application of dye to dye-sensitized solar cell
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  • Indoline-dithienoquinoxaline-dibenzo[a,c]phenazine dye and application of dye to dye-sensitized solar cell

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Indoline-dithienoquinoxaline-dibenzo[a,c]phenazine dye IQ(R 1 =C 8 h 17 (n-octyl), R 2 =C 8 h 17 (n-octyl), ie R 1 and R 2 The same is the synthesis of a linear alkyl group containing 8 carbon atoms, X is a sulfur atom), and the synthetic route is as follows:

[0023]

[0024]

[0025] Concrete synthesis process comprises the following steps:

[0026] (1) Synthesis of compound 2

[0027]

[0028] In a nitrogen atmosphere, 4.6g (10mmol) of compound 1 was dissolved in 25mL of tetrahydrofuran (THF), then cooled to 0°C, N-bromosuccinimide (4.4g, 25mmol) was added to the reaction solution, and to normal temperature, reacted for 12h, added 30mL of water to quench the reaction, and extracted with dichloromethane; the organic phase was washed twice with water, dried, concentrated, and the crude product was recrystallized with 10mL of n-hexane to obtain 5g of white solid, namely compound 2, yield 80%. The melting point is 100.3-101.6°C. 1 H NMR (400MHz, Chlor...

Embodiment 2

[0043] The synthetic dye IQ of embodiment 1 is carried out ultraviolet-visible absorption spectrum test, and test condition is as follows:

[0044] Solvent: tetrahydrofuran;

[0045] Concentration: 2×10 -5 M;

[0046] temperature: room temperature;

[0047] Instrument: Shimadzu UV-2450 UV-Vis spectrophotometer.

[0048] The UV-Vis absorption spectrum obtained from the test is shown as figure 1 shown, from figure 1 It can be seen that in the tetrahydrofuran solution, the dye IQ exhibits two absorption peaks, one is the absorption peak of the π-π* transition, and the other is the absorption peak of the intramolecular charge transfer (ICT), and the molar extinction coefficient of the dye is relatively High, wide absorption range, exceeding 24000M in the range of 400-550nm - 1 cm -1 , which indicates that the dye IQ has a good light-harvesting ability.

Embodiment 3

[0050] Fabrication of dye-sensitized solar cells

[0051] The dye IQ prepared in Example 1 was used as a sensitizer in a dye-sensitized solar cell to prepare a dye-sensitized solar cell based on the dye IQ sensitizer.

[0052] Dye-sensitized solar cells are mainly composed of conductive glass substrates (F-doped SnO 2 Transparent conductive glass (FTO), photoanode, sensitizer, electrolyte solution and platinum counter electrode (also known as photocathode, platinum-coated conductive glass); among them, the conductive glass surface of the photoanode substrate is covered with nanoporous TiO 2 Thin film used to adsorb dyes; the substrate of the counter electrode is coated with Pt catalyst; 2 The periphery of the film is sealed with a sealing material to form a closed cavity, and the cavity is filled with an electrolyte solution and a sensitizer (ie indoline-dithienoquinoxaline-dibenzo[a,c]phenazine dye IQ).

[0053] The specific preparation process of dye-sensitized solar cell...

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Abstract

The invention discloses indoline-dithienoquinoxaline-dibenzo[a,c]phenazine dye and application of the dye to a dye-sensitized solar cell. The dye is a D-A-pi-A pure organic dye, wherein an indoline group is taken as an electron donor; a dithienoquinoxaline group and a thiophene group are taken as pi bridges; a cyanoacetic acid group is taken as an electron donor as well as an anchoring group; meanwhile a dibenzo[a,c]phenazine group is taken as an electronic assisted donor. The dibenzo[a,c]phenazine assisted electronic donor is introduced into dye molecules, so that the conjugacy of the dye molecules is enhanced, and the molecular orbital energy level is regulated; intramolecular electron transfer is promoted through a rigid plane of conjugated big pi-bridge dioctyl dithienoquinoxaline, andthe accumulation of the dye is restrained through an alkyl chain, so that the spectrum response range is expanded effectively, and the electronic life is prolonged; the dye has good light absorptioncapability; the dye-sensitized solar cell based on the dye can obtain big photocurrent, so that relatively high photoelectric conversion efficiency is achieved.

Description

technical field [0001] The invention relates to the technical field of organic dyes, in particular to sensitizing dyes for dye-sensitized solar cells and applications thereof. Background technique [0002] Dye-sensitized solar cells (DSSCs) are a novel device for converting solar energy into electricity. This type of battery has attracted great attention because of its facile fabrication and high energy conversion efficiency enabling its indoor or commercial applications. Its advantages lie in its cheap cost and simple preparation process. For high-performance dye-sensitized solar cells, the structure of the sensitizing dye plays a decisive role in the photoelectric conversion efficiency of the cell. At present, polypyridine ruthenium complex dyes have the highest photoelectric conversion efficiency, but such dyes require the use of rare metal ruthenium and are difficult to separate and purify. However, pure organic dyes have been widely developed and applied recently bec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/14C09B17/00H01G9/20H01L51/46
CPCH01G9/2004C07D495/14C09B17/005H10K85/655H10K85/657H10K85/6572Y02E10/542Y02E10/549
Inventor 曹德榕肖泰
Owner SOUTH CHINA UNIV OF TECH
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