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Can Polystyrene be Optically Active?
Author(s) -
Wulff Günter,
Dhal Pradeep K.
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198901961
Subject(s) - diad , polystyrene , optically active , stereocenter , copolymer , styrene , specific rotation , materials science , polymer chemistry , optical rotation , chemistry , stereochemistry , organic chemistry , polymer , enantioselective synthesis , catalysis , composite material
The first synthesis of optically active polystyrene with [α] 365 30as large as −3.5°was achieved by using an optically active template compound ( D ‐mannitol derivative containing two p ‐vinylphenylboronic acid groups). This compound was copolymerized with styrene. The copolymer contains p ‐dihydroxyboryl‐substituted distyrene diads of defined configuration, which are separated by atactic polystyrene segments. Reduction of the B(OH) 2 groups affords polystyrene. In such an arrangement, approximately 25% of the diad centers are stereogenic and chirotopic (asymmetric), thus contributing to the optical rotation of the molecule.