A Convenient Synthesis of Benzo[1,2-b:6,5-b′:3,4-c′′]trithiophenes Starting from Thiophene

Hyokwon Kim; Kyukwan Zong

doi:10.1055/s-0037-1611017

Synthesis, Table of Contents

Synthesis 2019; 51(04): 859-864
DOI: 10.1055/s-0037-1611017

paper

A Convenient Synthesis of Benzo[1,2-b:6,5-b′:3,4-c′′]trithiophenes Starting from Thiophene

Authors

Hyokwon Kim
Kyukwan Zong*

Institute of Fusion Science, Division of Science Education, Department of Chemistry Education, Chonbuk National University, Jeonju, Jeonbuk, 561-756, Republic of Korea Email: kzong@jbnu.ac.kr

Abstract

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Abstract

A series of benzo[1,2-b:6,5-b′:3,4-c′′]trithiophenes were synthesized in four steps starting from thiophene. Thiophene was converted into 2,5-dialkylthiophenes upon dilithiation followed by treatment with various alkyl halides. The reaction of 2,5-dialkylthiophenes with Br₂ easily afforded the corresponding 2,5-dialkyl-3,4-dibromothiophenes. Their coupling reactions with 3-tributyltinthiophene in the presence of a Pd catalyst and the subsequent oxidative ring-closing reactions led to target compounds in moderate to good yields.

Key words

thiophene - benzotrithiophene - donor - photovoltaics - semiconductor

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References

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