Stereocontrolled Synthesis and Optical Properties of All-cis Poly(phenylene vinylenes) (PPVs): A Method for Direct Patterning of PPVs

Geometrically pure, all-cis poly(phenylene vinylenes) (PPVs) are synthesized by Suzuki-Miyaura-type polycondensation of 2,5-dioctyloxy-1,4-benzenediboronic acid with (Z,Z)-bis(2-bromoethenyl)benzenes, which are prepared by ruthenium-catalyzed (Z)-selective double hydrosilylation of diethynylbenzenes, followed by bromodesilylation of the resulting (Z,Z)-bis(2-silylethenyl)benzenes with N-bromosuccinimide. The all-cis PPVs thus obtained undergo one-way photoisomerization to the corresponding trans-PPVs both in solution and in the solid. This phenomenon is applied to direct microscale patterning of PPVs onto a quartz substrate.

J. Am. Chem. Soc., 127 (12), 4350 -4353, 2005. 10.1021/ja042853n