Porphyrin copolymer containing thienothiadiazole units, preparation method and uses thereof

A technology of porphyrin copolymer and thiadiazole, which can be used in chemical instruments and methods, electrical components, and final product manufacturing, etc., and can solve problems such as low photoelectric conversion efficiency.

Inactive Publication Date: 2014-03-12
OCEANS KING LIGHTING SCI&TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, the photoelectric conversion efficiency of organic solar cells is still much lower than that of inorganic solar cells

Method used

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  • Porphyrin copolymer containing thienothiadiazole units, preparation method and uses thereof
  • Porphyrin copolymer containing thienothiadiazole units, preparation method and uses thereof
  • Porphyrin copolymer containing thienothiadiazole units, preparation method and uses thereof

Examples

Experimental program
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preparation example Construction

[0033] see figure 2 , the preparation method of above-mentioned porphyrin copolymer containing thienothiadiazole unit comprises the steps:

[0034] S10, respectively provide compounds A, B, C, D represented by the following structural formula,

[0035] where R 1 , R 2 , R 3 , R 4 for the same or different C 1 -C 32 the alkyl group;

[0036] S20, in a system containing a catalyst, an oxidizing agent and an organic solvent, the compounds A, B, and C are subjected to polycondensation and oxidation reactions to generate 5,15-di(9,9-dialkylfluorene)porphyrin;

[0037] S30, in a system containing a catalyst and an organic solvent, 5,15-bis(9,9-dialkylfluorene)porphyrin is subjected to a bromination substitution reaction to generate 5,15-dibromo-10,20-bis( 9,9-dialkylfluorene) porphyrin;

[0038] S40, in the presence of a catalyst and an organic solvent, 5,15-dibromo-10,20-two (9,9-dialkylfluorene) porphyrin and compound D are subjected to a Suzuki coupling reaction to ob...

Embodiment 1

[0079] The present embodiment 1 provides 10,20-bis(9,9-dioctylfluorene)porphyrin-thieno[3,4-c][1,2,5]thiadiazole copolymer with the following structure. The structural formula of the compound is shown in the product of the reaction formula of the fourth step. The preparation steps of above-mentioned polymer are as follows:

[0080] 1. 5,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) thieno[3,4-c][1,2,5] The preparation of thiadiazole, its preparation involves reaction formula as follows:

[0081]

[0082] The specific process is: under the protection of nitrogen, add p-9,10-dibromothieno[3,4-c][1,2,5]thiadiazole (9.0g, 0.03mol) into the three-necked flask, add 200ml of tetrahydrofuran solvent, slowly inject n-butyllithium (25.2mL, 2.5M, 0.06mol) with a syringe at -78°C, continue stirring for 2h, inject 2-isopropyl lithium with a syringe at -78°C Oxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13 mL, 0.06 mol), stirred overnight at room temperature. Saturated aqueous sodium...

Embodiment 2

[0094]This Example 2 provides 10-(9-methyl-9-octylfluorene)-20-(9-decyl-9-hexadecylfluorene)porphyrin-thieno[3,4-c with the following structure ][1,2,5]thiadiazole copolymer, the structural formula of this polymer is shown in the product of the reaction formula of the fourth step. The preparation steps of above-mentioned polymer are as follows:

[0095] 1. 5,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) thieno[3,4-c][1,2,5] The preparation of thiadiazole is detailed in Example 1.

[0096] Two, the preparation of 10-(9-methyl-9-octylfluorene)-20-(9-decyl-9-hexadecylfluorene) porphyrin, this step involves the reaction formula as follows:

[0097]

[0098] The specific process is: set up an anhydrous and oxygen-free device, weigh the intermediates 9-methyl-9-octylfluorene (0.32g, 1mmol), 9-decyl-9-hexadecylfluorene (0.56g, 1mmol) ), dipyrromethane (0.30g, 2mmol), dissolved in 250ml of dichloromethane, nitrogen 30min, inject 2ml of trifluoroacetic acid into the syringe, sti...

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Abstract

A porphyrin copolymer containing thienothiadiazole units, preparation method and uses thereof are disclosed. The copolymer has the structural formula (I), wherein: R 1 , R 2 , R 3 , R 4 are same or different and each represents a C 1 -C 32 alkyl; n is an integer of 1-100. The copolymer comprises fluorene units, thienothiadiazole units and porphyrin units, which enhance the density of electron cloud in copolymer skeleton, make the band-gap of the copolymer become narrow, thereby broaden the spectral response range of the copolymer, and improve the photoelectric transformation efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic materials, and in particular relates to a porphyrin copolymer containing thienothiadiazole units, its preparation method and application. Background technique [0002] Today's world economy is mainly based on fossil energy, such as coal, oil and natural gas. However, these non-renewable fossil energy sources are constantly being exhausted. Since the beginning of the 21st century, global energy issues and the ensuing environmental pollution and climate warming have become increasingly prominent and gradually intensified. Solar energy is considered to be one of the most promising renewable energy sources because of its widespread and vast distribution, large amount of resources, no pollution, cleanliness, safety, and easy access. [0003] In order to make full use of the energy irradiated by sunlight, people continue to develop new materials that can absorb sunlight. Among them, inorganic semicond...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/42
CPCC08G2261/148H01L51/424H01L51/009C09K2211/1483C09K2211/1466H01L51/0077C08G2261/3221H01L51/0043C08G61/123C08G2261/124C08G2261/91H01L51/0558C08G61/124C08G61/126C08G2261/3243C08F236/20H01L51/5012C09K11/06C09K2211/1029C09K2211/1011C08G2261/3246Y02E10/549Y02P70/50H10K85/151H10K85/30H10K85/361H10K10/484H10K30/20H10K50/11H10K30/50
Inventor 周明杰黄杰刘贻锦
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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