A kind of dianilino-three polyindene-bodipy derivative ternary system organic dyes and its preparation method and application

A dianiline-based, ternary system technology, applied in the direction of organic dyes, styrene-based dyes, methenyl/polymethine-based dyes, etc., to achieve good application prospects, simple and easy preparation method, and enhanced light absorption effect

Active Publication Date: 2022-04-19
NANJING FORESTRY UNIV
View PDF3 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of dianilino-three polyindene-bodipy derivative ternary system organic dyes and its preparation method and application
  • A kind of dianilino-three polyindene-bodipy derivative ternary system organic dyes and its preparation method and application
  • A kind of dianilino-three polyindene-bodipy derivative ternary system organic dyes and its preparation method and application

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 (40 mg). 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]

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The present invention relates to a class of diphenylamino-tripolyindene-BODIPY derivative ternary system organic dyes and a preparation method and application thereof. The BODIPY derivatives modified at positions 3 and 5 are covalently bonded with diphenylamine derivatives through chemical reactions. They are respectively connected to the 2, 7, and 12 positions of trisindene to form a D-A-π-D molecular system. The introduction of diphenylamine is conducive to the delocalization of π electrons, and promotes intramolecular charge transfer, thereby improving the photoelectric conversion of organic dye molecules. Efficiency; the organic dye provided by the invention has strong light absorption ability and can effectively dissociate excitons; the synthesis method provided by the invention is simple, the reaction conditions are mild, the selectivity is good, and the environmental pollution is small; it can be used in organic solar energy Good results have been obtained in batteries, and the photoelectric conversion efficiency can reach 13.32%. The organic dye can be used in the field of solar batteries.

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Patents(China)
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap