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Preparation and application of diisoindigo monomer and its benzodithiophene bistin copolymer

A technology of benzodithiophene and thiophene double tin is applied in the field of preparation of bisisoindigo monomer and benzodithiophene double tin copolymer, which can solve the problems of unfavorable industrial production, troublesome purification, high cost, and achieve good Application prospect, simple and effective synthesis method, low cost effect

Inactive Publication Date: 2018-05-29
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Under the catalysis of hydrochloric acid, the isoindigo without alkyl chain is synthesized, and finally the isoindigo with alkyl chain is synthesized by alkylation under the action of potassium carbonate. This kind of yield is too low, the cost is too high, the purification is troublesome, and it is not conducive to industrialization Production

Method used

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  • Preparation and application of diisoindigo monomer and its benzodithiophene bistin copolymer
  • Preparation and application of diisoindigo monomer and its benzodithiophene bistin copolymer
  • Preparation and application of diisoindigo monomer and its benzodithiophene bistin copolymer

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Embodiment 1

[0039] This embodiment provides a diisoindigo monomer (DIIDT) based on thiophene unit connection and its benzodithiophene bistin copolymer (PDIIDT-BDTO and PDIIDT-BDTT), its structural formula is shown in Table 1, and its single For the synthetic route of body DIDT see figure 1 , the synthesis of polymers PDIIDT-BDTO and PDIIDT-BDTT see figure 2 shown.

[0040] Table 1

[0041]

[0042] This embodiment also relates to the preparation method of polymer PDIIDT-BDTO and PDIIDT-BDTT, comprising the steps of:

[0043] (a) Synthesis of intermediate compound benzodithiophene bistin monomer

[0044] The structural formula of benzodithiophene ditin monomer is

[0045] For its detailed preparation method, see the literature "Hwang, Y.J; Kim, F.S; Xin, H; Jenekhe, S.A; New Thienothiadiazole-Based Conjugated Copolymers for Electronics and Optoelectronics. Macromolecules 2012, 45, 3732-3739; Cheng, Y.S; Chen, S.A; Fullerene Derivative-Doped Zinc Oxide Nanofilm as the Cathode of I...

Embodiment 2

[0072] This embodiment relates to the H NMR carbon NMR spectrum of the monomer DIIDT in Example 1, the ultraviolet absorption spectrum and electrochemical properties of the polymers PDIIDT-BDTO and PDIIDT-BDTT. image 3 and Figure 4 The H NMR and C NMR spectra of monomer DIDT are given respectively. Figure 5 The UV absorption spectra of polymers PDIIDT-BDTO and PDIIDT-BDTT in chloroform are given, and the λ in chloroform solutions of PDIIDT-BDTO and PDIIDT-BDTT max abs Very close, almost coincident, respectively 695nm and 698nm; Figure 6 The solid film UV absorption spectra of the polymers PDIIDT-BDTO and PDIIDT-BDTT are given, and the UV-vis absorption of the polymer solid film λ max abs PDIIDT-BDTO 697nm, PDIIDT-BDTT 702nm, respectively red-shifted 2nm and 4nm, PDIIDT-BDTO and PDIIDT-BDTT λ onset abs are 790nm and 800nm ​​respectively, the corresponding E g opt (Eg opt =1240 / λ onset abs ) are 1.57eV and 1.55eV, respectively. Figure 7 The cyclic voltammetry cu...

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Abstract

The invention discloses a di-bioxindol monomer and a benzodithiophene double-tin copolymer preparation method, and a purpose thereof. A monomer DIIDT has a structural formula shown as a formula I in a specification, wherein R1 and R2 are C8-C20 alkyl chains. Under condition that Pd(dba)3 is taken as a catalyst, P(o-tol)3 is taken as a ligand, and anhydrous toluene is taken as a solvent, the monomer DIIDT and the benzodithiophene double-tin are polymerized, and the copolymer can be obtained through extraction by soxhlet. The disclosed synthetic method is simple and effective, the distribution of the obtained target polymer molecular weight is narrow; the ultra-violet spectrum absorption is strong, ultra-violet spectrum is wide, the material can be processed with a solution, and the copolymer has good application prospect in a photovoltaic device.

Description

technical field [0001] The invention relates to a solution-processable organic semiconductor material, in particular to the preparation and application of diisoindigo monomer (DIIDT) based on thiophene unit connection and its benzodithiophene ditin copolymer. Background technique [0002] Energy consumption in today's world is increasing, but non-renewable energy sources such as coal, oil, and natural gas are increasingly exhausted. Using solar energy is an effective way to solve energy problems faced by human society. [0003] Due to its good conjugation effect and strong light absorption ability, isoindigo is widely used in OPV and OFET. Under the catalysis of hydrochloric acid, the isoindigo without alkyl chain is synthesized, and finally the isoindigo with alkyl chain is synthesized by alkylation under the action of potassium carbonate. This kind of yield is too low, the cost is too high, the purification is troublesome, and it is not conducive to industrialization Prod...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/14C08G61/12
CPCC07D409/14C08G61/126C08G2261/12C08G2261/3246C08G2261/91
Inventor 吴建周祥梅张清刘壮峻卞燕南
Owner SHANGHAI JIAOTONG UNIV
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