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Helix‐Sense‐Selective Polymerization of Achiral Bis(hydroxymethyl)phenylacetylenes Bearing Alkyl Groups of Different Lengths |
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| Authors: | Shingo Hadano Takuya Kishimoto Tomonori Hattori Daisuke Tanioka Masahiro Teraguchi Toshiki Aoki Takashi Kaneko Takeshi Namikoshi Edy Marwanta |
| Affiliation: | 1. Venture Business Laboratory, Niigata University, Ikarashi 2‐8050, Nishi‐ku, Niigata 950‐2181, Japan;2. Graduate School of Science and Technology, Niigata University, Ikarashi 2‐8050, Nishi‐ku, Niigata 950‐2181, Japan;3. Department of Chemistry and Chemical Engineering, Faculty of Engineering, Niigata University, Ikarashi 2‐8050, Nishi‐ku, Niigata 950‐2181, Japan;4. Center for Transdisciplinary Research, Niigata University, Ikarashi 2‐8050, Nishi‐ku, Niigata 950‐2181, Japan |
| Abstract: | 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 intermolecular hydrogen bonds between the hydroxyl groups, and stabilized their one‐handed helical structure by promoting the formation of intramolecular hydrogen bonds.  |
| Keywords: | alkyl groups chiral catalytic systems enantioselective permeation helix‐sense‐selective polymerization hydroxy groups phenylacetylenes |