Design and synthesis of a 256-membered pi-conjugated oligomer library of regioregular head-to-tail coupled quater(3-arylthiophene)s.
The rapid solid-phase synthesis of pi-conjugated oligomers is demonstrated by utilizing the parallel and the "mix-and-split" methods for the preparation of a library of 256 regioregular head-to-tail coupled oligo(3-arylthiophene)s. Chemical diversity was introduced to the growing oligomer starting from four resin-bound 3-(p-X-phenyl)-2-silylthiophenes via an iterative sequence of iodinations and Suzuki cross-coupling reactions with four 3-(p-X-phenyl)thiophene boronic esters (X = CF(3), H, CH(3), OCH(3)). Liberation from the solid support with TFA and subsequent chromatographic purification by normal-phase LC-MS provided all 256 regioregular head-to-tail coupled quater(3-arylthiophene)s.
Briehn
Christoph A
CA
Department of Organic Chemistry II (Organic Materials and Combinatorial Chemistry), University of Ulm, Albert-Einstein-Allee 11, D-89081 Ulm, Germany.
Bäuerle
Peter
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