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Diphenylamino-truxene-BODIPY derivative ternary system organic dye as well as preparation method and application thereof

A diphenylamine-based, ternary system technology, applied in the direction of organic dyes, styryl dyes, methine-based/polymethine-based dyes, etc., to achieve mild and efficient reaction conditions, enhanced light absorption capacity, and good application prospects.

Active Publication Date: 2021-08-24
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the BODIPY derivatives modified at the 3 and 5 positions and the diphenylamine derivatives can be covalently connected to the 2, 7 and 12 positions of the tripolyindene to form a molecular system of D-A-π-D, which can have It is conducive to the delocalization of π electrons, promotes intramolecular charge transfer, and improves the photoelectric conversion efficiency of dye molecules, thereby synthesizing a class of organic dye molecules with novel structure, simple preparation method and excellent performance. There is no literature report on the solar energy application of this structure.

Method used

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  • Diphenylamino-truxene-BODIPY derivative ternary system organic dye as well as preparation method and application thereof
  • Diphenylamino-truxene-BODIPY derivative ternary system organic dye as well as preparation method and application thereof
  • Diphenylamino-truxene-BODIPY derivative ternary system organic dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Compound 2-bromo-7,12-bis(N,N-diphenylamino)-tripolyindene (92.4 mg, 0.1 mmol), compound 1,7-dimethyl-3,5-bis (4-Methoxystyryl)-8-(boronate)-BODIPY 1a (103 mg, 0.15 mmol), anhydrous cesium carbonate (330 mg, 1 mmol) were dissolved in 20 mL of tetrahydrofuran, and 2 mL of water was added thereto with 2mL of methanol, tetrakis(triphenylphosphine)palladium (18mg, 0.015mmol) was quickly added thereto under the protection of argon, and the temperature was raised to 65°C for 12h. After the reaction was completed, the solvent was spin-dried, extracted with dichloromethane, washed with saturated sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate, distilled under reduced pressure to spin-dry the solvent, and dichloromethane-petroleum ether (v:v=1: 1) was separated and purified by silica gel chromatography as the eluent to obtain dark brown solid 2a (66 mg). 1 H NMR (CDCl 3 , 600MHz, ppm): δ8.39(d, J=10.2Hz, 1H), 8.19(d, J=3.6Hz, 1H), 8.12(d, J=...

Embodiment 2

[0029] Compound 2-bromo-7,12-bis(N,N-diphenylamino)-tripolyindene (92.4 mg, 0.1 mmol), compound 1,7-dimethyl-3,5-bis (4-N,N-Diphenylaminostyryl)-8-(boronate)-BODIPY 1b (144.1 mg, 0.15 mmol), anhydrous cesium carbonate (330 mg, 1 mmol) were dissolved in 20 mL of tetrahydrofuran, and 2 mL of water and 2 mL of methanol were added thereto, and tetrakis(triphenylphosphine)palladium (18 mg, 0.015 mmol) was quickly added thereto under the protection of argon, and the temperature was raised to 68° C. for 12 h. After the reaction was completed, the solvent was spin-dried, extracted with dichloromethane, washed with saturated sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate, distilled under reduced pressure to spin-dry the solvent, and dichloromethane-petroleum ether (v:v=1: 1) was separated and purified by silica gel chromatography as the eluent to obtain dark brown solid 2b (40mg). 1 H NMR (CDCl 3 , 600MHz, ppm): δ8.38(d, J=8.4Hz, 1H), 8.19(d, J=8....

Embodiment 3

[0032] In the present invention, 2a and 2b in the embodiment 1 and 2 are used as electron donors and PC71BM and Y6 as electron acceptors to prepare solar cells respectively, and the efficiency of the device is tested respectively. The photoelectric conversion efficiency current density-voltage curve is shown in Figure 4 . The performance of the above devices is summarized in the following table:

[0033]

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Abstract

The invention relates to a diphenylamino-truxene-BODIPY derivative ternary system organic dye as well as a preparation method and application thereof. A 3-site and 5-site modified BODIPY derivative and a diphenylamine derivative are respectively connected to 2, 7 and 12 sites of truxene through covalent bonds through a chemical reaction to construct a D-A-pi-D molecular system, introduction of diphenylamine is beneficial to pi electron delocalization, intramolecular charge transfer is promoted, so that the photoelectric conversion efficiency of organic dye molecules is improved; the organic dye provided by the invention has strong light absorption capability, and can effectively perform exciton dissociation; the synthesis method provided by the invention is simple, mild in reaction condition, relatively good in selectivity and small in environmental pollution; when the organic dye is used in an organic solar cell, a good effect is obtained, and the photoelectric conversion efficiency can reach 13.32%; and the organic dye can be used in the field of solar cells.

Description

technical field [0001] The invention belongs to the field of fine organic synthesis and solar cells, and in particular relates to a class of dianilino-triindene-BODIPY derivative ternary system organic dyes and a preparation method and application thereof. Background technique [0002] Due to the increasing energy crisis caused by environmental problems and the depletion of petroleum resources, solar cells have attracted widespread attention as a renewable and environmentally friendly energy source. In the development of solar energy conversion technologies, silicon solar cells are the commercially dominant photovoltaic technology. However, due to some unique advantages such as high transparency, low cost, good flexibility, abundant availability, large area, uncomplicated fabrication, and light weight, organic solar cells (OSCs) are gradually becoming a promising method for solar energy conversion. technology for electrical energy. Organic solar cells usually consist of a ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09B23/14C09K11/06H01G9/20
CPCC07F5/022C09B23/145C09K11/06H01G9/2059C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1055Y02E10/542Y02P70/50
Inventor 徐海军李鹏飞蔡方建郭颖欣蔡正春
Owner NANJING FORESTRY UNIV
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