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Synthesis 2002(8): 1004-1006
DOI: 10.1055/s-2002-31959
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

dl-BiTOT - A Novel Building Block for Electroactive Oligomers and Polymers in Semiconductor Applications

Fredrik von Kieseritzky, Jonas Hellberg*
Dept of Chemistry, Organic Chemistry, Royal Institute of Technology, 100 44 Stockholm, Sweden
Fax: +46(8)7912333; e-Mail: jhel@kth.se;
Further Information

Publication History

Received 13 February 2002
Publication Date:
03 June 2002 (online)

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Abstract

The title compound dl-biTOT (1, dl-2,2′,3,3′-tetrahydro-2,2′-bithieno[3,2-b][1,4]oxathiine) was prepared in a five-step synthesis using cheap and readily available starting materials, with an overall yield of 50%. Compound 1 is believed to display interesting and unique properties as a building block in oligomer and polymer applications in the rapidly growing field of organic semiconductors. A new and superior method to oxidize dithiothreitol (Cleland’s reagent), that operates rapidly and cleanly on a multigram scale is also reported.

Key words

electroactive materials - building blocks - biaryls - heterocycles - oxidations

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von Kieseritzky, F.; Hellberg, J., submitted to J. Org. Chem.