Efficient solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-alkylthiophene)s up to a dodecamer

Thomas Kirschbaum; Christoph A. Briehn; Peter Bäuerle

doi:10.1039/B000123F

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Efficient solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-alkylthiophene)s up to a dodecamer

Thomas Kirschbaum,^a Christoph A. Briehn^a and Peter Bäuerle*^a

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* Corresponding authors

^a Department Organic Chemistry II (Organic Materials and Combinatorial Chemistry), University of Ulm, Albert-Einstein-Allee 11, Ulm, Germany
E-mail: peter.baeuerle@chemie.uni-ulm.de

Abstract

Solid-phase synthesis of isomerically pure head-to-tail-coupled (HT) oligo(3-hexylthiophene)s on chloromethylated polystyrene resin has been developed. Using novel sequences of iodination and Suzuki cross-coupling reaction, a series up to a dodecamer has been synthesized in high yield and purity. Removal of the conjugated oligomers from solid support as methyl esters, saponification and decarboxylation to the HT-coupled oligo(3-alkylthiophene)s could be effectively achieved.

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Article information

DOI: https://doi.org/10.1039/B000123F
Article type: Paper
Submitted: 07 Jan 2000
Accepted: 29 Feb 2000
First published: 29 Mar 2000

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J. Chem. Soc., Perkin Trans. 1, 2000, 1211-1216

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Efficient solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-alkylthiophene)s up to a dodecamer

T. Kirschbaum, C. A. Briehn and P. Bäuerle, J. Chem. Soc., Perkin Trans. 1, 2000, 1211 DOI: 10.1039/B000123F

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Journal of the Chemical Society, Perkin Transactions 1

Efficient solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-alkylthiophene)s up to a dodecamer

Abstract

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Efficient solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-alkylthiophene)s up to a dodecamer

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