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  • Title: Stereoselective synthesis of cis- and trans-oligo(phenylenevinylene)s via palladium-catalyzed cross-coupling reactions.
    Author: Katayama H, Nagao M, Ozawa F, Ikegami M, Arai T.
    Journal: J Org Chem; 2006 Mar 31; 71(7):2699-705. PubMed ID: 16555823.
    Abstract:
    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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