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Paper | Regular issue | Vol 85, No. 2, 2012, pp.355-364
Published online, 10th January, 2012
DOI: 10.3987/COM-11-12390
One-Pot Synthesis of 4,8-Dialkylbenzo[1,2-b:4,5-b’]dithiophenes

Ted M. Pappenfus,* Daniel T. Seidenkranz, and Eric W. Reinheimer

*Department of Chemistry, Division of Science and Mathematics, University of Minnesota, 600 East 4th Street, Morris, MN 56267-2128, U.S.A.

Abstract

Two-step, one-pot syntheses are described for the preparation of 4,8-dialkylbenzo[1,2-b:4,5-b]dithiophenes (BDTs) from alkyllithium or alkyl Grignard reagents. The yields for various alkyl groups used in this procedure are comparable with or exceed those of previously reported methods. The electronic and redox properties of dialkyl-BDTs are compared with the dialkoxy-BDT, 4,8-bis(hexyloxy)benzo[1,2-b:4,5-b']dithiophene. The stabilized HOMO levels of dialkyl-BDTs suggest they are promising building blocks for use in organic photovoltaics such as bulk heterojunction solar cells.