Stereoselective synthesis of cis- and trans-oligo(phenylenevinylene)s via palladium-catalyzed cross-coupling reactions.
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.
Katayama
Hiroyuki
H
International Research Center for Elements Science (IRCELS), Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
Nagao
Masato
M
Ozawa
Fumiyuki
F
Ikegami
Masashi
M
Arai
Tatsuo
T
D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011145:Polyvinyls / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001897:Boronic Acids; D006842:Hydrocarbons, Brominated; D011145:Polyvinyls; C470024:poly(4-phenylenevinylene); D010165:Palladium