Abstract
All-cis and all-trans isomers of poly[(arylenevinylene)-alt-(5-octyloxy-1,3-phenylenevinylene)]s having three kinds of arylene groups (PmPVs: arylene = m-phenylene (1a), p-phenylene (1b), 4,4′-biphenylene (1c)) have been synthesized in almost perfect stereoregularity by two types of palladium-catalyzed polycondensation reactions, respectively. Suzuki−Miyaura-type polycondensation of (Z,Z)-bis(2-bromoethenyl)arenes with 5-octyloxy-1,3-benzenediboronic acid pinacolate affords all-cis 1a−c, whereas Hiyama-type polycondensation of (E,E)-bis(2-silylethenyl)arenes with 5-octyloxy-1,3-diiodobenzene forms all-trans 1a−c. The resulting polymers with relatively short effective π-conjugation lengths interrupted by m-phenylene units undergo two-way photoisomerization to give PmPVs containing cis- and trans-vinylene groups in nearly 1:1 ratios irrespective of the arylene groups of staring polymers.
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