Design and Synthesis of a 256-Membered π-Conjugated Oligomer Library of Regioregular Head-to-Tail Coupled Quater (3-arylthiophene)s

摘要

The rapid solid-phase synthesis of π-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.