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Long‐distance chirality transfer in polymerization of isocyanides bearing a remote chiral group
Author(s) -
Chen Jian Ping,
Gao Jian Ping,
Wang Zhi Yuan
Publication year - 1997
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/(sici)1097-0126(199709)44:1<83::aid-pi820>3.0.co;2-t
Subject(s) - helicene , chirality (physics) , polymerization , circular dichroism , stereocenter , cotton effect , imide , materials science , photochemistry , chemistry , polymer chemistry , stereochemistry , enantioselective synthesis , organic chemistry , physics , chiral symmetry breaking , molecule , polymer , catalysis , symmetry breaking , nambu–jona lasinio model , quantum mechanics
A long‐distance chirality transfer was observed in the Ni( II )‐catalysed polymerization of 5,6,9,10‐tetrahydro[5]helicene‐ and [5]helicene‐based iso‐cyanides bearing a remote chiral group. Polymerizations of N ‐[( S )‐(‐)‐α‐methyl‐benzyl]‐3‐isocyanido‐5,6,9,10‐tetrahydro[5]helicene‐7,8‐dicarboxylic imide and N ‐[( S )‐(‐)‐α‐methylbenzyl]‐3‐isocyanido‐[5]helicene‐7,8‐dicarboxylic imide, which are laevorotatory, afforded optically active polyisocyanides having dextro‐rotations at 589nm and circular dichroism exciton couplets in the UV/vis. region. The chirality transfer from the remote stereogenic centre to the reactive isocyanido group was responsible for the helix‐sense‐selective polymerization. ©1997 SCI
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