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Synfacts 2007(1): 0046-0046  
DOI: 10.1055/s-2006-955678
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Hexafluorocyclopentene-Annelated Thiophene Monomer

Contributor(s): Timothy M. Swager, Eric L. Dane
Y. Ie, Y. Umemoto, T. Kaneda, Y. Aso*
Osaka University, Japan
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

The authors combine two fluorination techniques to achieve a hexafluorocyclopentene-annelated thiophene monomer. They use this monomer to synthesize a series of oligomers to investigate the effects of adding the highly electron-withdrawing substituents. Based on spectro­scopic measurements, X-ray crystal structure analysis, and electrochemical data, the authors argue that the fluorinated group enhances the electronegativity of the oligiothiophenes without significantly interfering with the conjugation between the thiophene units.