Study Towards the Synthesis of 5,5’-bis(4-chlorophenyl)-2,2’-bithiophene via 2-(4-chlorophenyl)-thiophene Oxidative Homocoupling Dimerization
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Authors
Berger, Spencer
Date of Issue
2025-04-25
Type
Presentation
Language
en_US
Subject Keywords
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Abstract
In this study, we are looking at how light driven oxidative homocoupling dimerization selectively creates a new carbon-carbon bond at the alpha position in thiophenes. By creating carbon-carbon bonds via light energy, this reaction has the potential to store energy which can be used as a renewable energy source. Scientists continue to grow an interest in using thiophene’s as a source of energy conservation. Herein, we report our results towards the synthesis of 5,5’-bis(4-chlorophenyl)-2,2’-bithiophene as a byproduct of two monomers, 2-(4-chlorophenyl) thiophene, that create carbon-carbon bonds in the alpha position. By first creating the monomer, we were able to use visible photons and a semiconductor to create this carbon-carbon bond for us. Throughout the summer we were able to successfully make 5,5’- bis(4-chlorophenyl)-2,2’-bithiophene from 4-chlorophenylboronic acid and 5,5-dibromothiophene using a Suzuki cross-coupling reaction. We also made 2-(4-chlorophenol)-thiophene via a Suzuki cross-coupling reaction with 4-chlorophenylboronic acid and 2-bromothiophene. The purity of the thiophenes was determined by H NMR. From there we took a UV-Vis of both thiophenes to observe the differences. With the pure 2-(4-chlorophenol)-thiophene, we performed spectro-electrochemistry using a semiconductor while simultaneously taking a UV-Vis spectrum to observe the chemical change in the thiophene. In the end we were able to see a chemical change in the thiophene as the UV-Vis changed as the cyclic voltammetry was performed. However, we feel confident that the monomer dimerized, but we do not have evidence to support our hypothesis at the time.
Description
SRF Poster. Abstract only.