Stereoselective synthesis of cis- and trans-oligo(phenylenevinylene)s via palladium-catalyzed cross-coupling reactions.

J Org Chem

International Research Center for Elements Science (IRCELS), Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.

Published: March 2006

cis-Oligo(phenylenevinylene)s (OPVs) are synthesized by Suzuki-Miyaura coupling of arylboronic acids with (Z)-bromoalkenes in over 96% geometrical purity. On the other hand, trans-oligo(phenylenevinylene)s can be synthesized by Hiyama coupling of aryl iodide with (E)-alkenylsilanes in almost perfect purities. Effect of pi-conjugation chain length on photoisomerization behavior of OPVs is described.

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http://dx.doi.org/10.1021/jo052602cDOI Listing

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