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A d-a-π-a type organic photosensitizing dye containing dithiophene cyclopentacarbazole and its preparation method and application

A technology of thiophenecyclopentacarbazole and photosensitizing dyes, applied in the fields of organic dyes, organic chemistry, photosensitizing equipment, etc., can solve problems such as unreported performance, achieve high photoelectric conversion efficiency, easy availability of raw materials, and good repeatability Effect

Active Publication Date: 2019-06-28
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although DTCC derivatives are widely used in the synthesis of high-performance organic / polymer semiconductor materials, DTCC-based organic photosensitizing dyes and their DSSCs device performance have not been reported. To develop such dyes and explore the relationship between the molecular structure of dyes and their photovoltaic properties relationship is of great significance

Method used

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  • A d-a-π-a type organic photosensitizing dye containing dithiophene cyclopentacarbazole and its preparation method and application
  • A d-a-π-a type organic photosensitizing dye containing dithiophene cyclopentacarbazole and its preparation method and application
  • A d-a-π-a type organic photosensitizing dye containing dithiophene cyclopentacarbazole and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0077] A kind of preparation method of the D-A-π-A type organic photosensitizing dye containing dithiophene cyclopentacarbazole of the present invention, specifically the organic photosensitizing dye DTCC-BT shown in preparation formula (I), its synthetic route as follows:

[0078]

[0079] Specifically, the compound DTCC-BT shown in formula (I) is prepared according to the following two-step reaction:

[0080] The first step: under nitrogen protection, add compound (DTCC-TPh) (1.22g, 0.94mmol), compound (BT) (0.34g, 0.94mmol), palladium acetate (0.04g, 0.19mmol) into a 100mL three-necked flask and toluene (50 mL), heated to 110°C for 5 hours. After cooling to room temperature, it was extracted with dichloromethane, and the collected organic phase was purified by column chromatography (the eluent was petroleum ether / ethyl acetate=20:1) to obtain a dark red solid (DTCC-BTE). was 38%.

[0081] The structural characterization data are as follows: 1 H NMR (400MHz, CDCl 3 )...

Embodiment 2

[0087] A kind of preparation method of D-A-π-A type organic photosensitizing dye containing dithiophene cyclopentacarbazole of the present invention, specifically is the organic photosensitizing dye DTCC-DFBT shown in preparation formula (I), its synthetic route as follows:

[0088]

[0089] Specifically, the compound DTCC-DFBT shown in formula (I) is prepared according to the following two-step reaction:

[0090] The first step: under nitrogen protection, add compound (DTCC-TPh) (1.0g, 0.78mmol), compound (DFBT) (0.31g, 0.78mmol), palladium acetate (0.04g, 0.16mmol) into a 100mL three-necked flask and toluene (50 mL), heated to 110°C for 5 hours. After cooling to room temperature, it was extracted with dichloromethane, and the collected organic phase was purified by column chromatography (the eluent was petroleum ether / ethyl acetate=20:1) to obtain a dark red solid (DTCC-DFBTE). was 43%.

[0091] The structural characterization data are as follows: 1 H NMR (400MHz, CDC...

Embodiment 3

[0097] A kind of preparation method of the D-A-π-A type organic photosensitizing dye containing dithiophene cyclopentacarbazole of the present invention, specifically the organic photosensitizing dye DTCC-PyT shown in preparation formula (I), its synthetic route as follows:

[0098]

[0099] Specifically, the compound DTCC-PyT shown in formula (I) is prepared according to the following two-step reaction:

[0100] The first step: under nitrogen protection, add compound (DTCC-TPh) (1.0g, 0.78mmol), compound (PyT) (0.28g, 0.78mmol), palladium acetate (0.04g, 0.16mmol) into a 100mL three-necked flask and toluene (50 mL), heated to 110°C for 5 hours. After cooling to room temperature, it was extracted with dichloromethane, and the collected organic phase was purified by column chromatography (eluent: petroleum ether / dichloromethane=2:1), and then recrystallized from ethanol to obtain a dark purple solid (DTCC- PyTE) in 37% yield. The structural characterization data are as fo...

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Abstract

The invention discloses D-A-pi-A organic photosensitized dye containing dithienocyclopentacarbazole (DTCC) and a preparation method and application thereof. The general structure of the organic photosensitized dye is represented by a formula (I); and the preparation method comprises the following steps: firstly performing a direct aromatization reaction by adopting M1 and M2 to prepare an M3 intermediate, and then performing a hydrolysis reaction to prepare the objective product. According to the intermediate and the synthetic route of the objective organic photosensitized dye provided by theinvention have the advantages that the raw materials are easy to obtain, the synthetic route is simple and effective, universality is high, repeatability is good and the like, and the synthetic routecan be applied to synthesis of various D-A-pi-A organic photosensitized dye containing DTCC groups. When the organic photosensitized dye is used to prepare dye-sensitized solar cells (DSSCs), energy converting efficiency of about 6.8% can be obtained, excellent potential of the organic photosensitized dye in the DSSCs is fully demonstrated, and the organic photosensitized dye has certain market prospects.

Description

technical field [0001] The invention belongs to the field of organic semiconductor materials, and relates to an organic photosensitizing dye used in dye-sensitized solar cells and its preparation method and application, in particular to a D-A-π-A type organic photosensitizer containing dithiophene cyclopentacarbazole Chemical dyes and their preparation methods and applications. Background technique [0002] In the 21st century, mankind is facing major energy crises and challenges such as the depletion of traditional fossil energy sources and environmental pollution. Therefore, seeking new renewable energy sources is one of the effective ways to solve this challenge. In recent years, organic solar cells have been extensively studied and important progress has been made. Among them, dye-sensitized solar cells (DSSCs) have attracted much attention due to the advantages of abundant raw materials, low cost, simple preparation process, and large-scale industrial production. As ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/14C07D495/00C09B57/00H01G9/20
CPCY02E10/542
Inventor 陈华杰曹群芳郑丽萍
Owner XIANGTAN UNIV
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