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Helix‐Sense‐Selective Polymerization of Achiral Bis(hydroxymethyl)phenylacetylenes Bearing Alkyl Groups of Different Lengths
Author(s) -
Hadano Shingo,
Kishimoto Takuya,
Hattori Tomonori,
Tanioka Daisuke,
Teraguchi Masahiro,
Aoki Toshiki,
Kaneko Takashi,
Namikoshi Takeshi,
Marwanta Edy
Publication year - 2009
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200800594
Subject(s) - alkyl , hydroxymethyl , polymerization , hydrogen bond , helix (gastropod) , chemistry , polymer chemistry , polymer , stereochemistry , molecule , organic chemistry , ecology , snail , biology
4‐Alkyloxy‐3,5‐bis(hydroxymethyl)phenylacetylenes with eight types of alkyl groups were synthesized and polymerized with a chiral catalytic system. We found that the length of the alkyl groups played a very important role in achieving helix‐sense‐selective polymerization. Five helix‐sense‐selective polymerizations were achieved resulting in polymers with alkyl groups whose chain length was longer than six. We think that the longer ‐ chain alkyl groups prevented the polymers from becoming insoluble by forming inter molecular hydrogen bonds between the hydroxyl groups, and stabilized their one‐handed helical structure by promoting the formation of intra molecular hydrogen bonds.