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Synthesis of Hydroxy Group‐Containing Poly( N ‐Propargylamides): Examination of the Secondary Structure and Chiral‐Recognition Ability of the Polymers
Author(s) -
Sanda Fumio,
Fujii Toru,
Tabei Junichi,
Shiotsuki Masashi,
Masuda Toshio
Publication year - 2008
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.200700374
Subject(s) - circular dichroism , chemistry , polymerization , polymer , polymer chemistry , optically active , stereochemistry , crystallography , organic chemistry
Optically‐active, novel N ‐propargylamides bearing hydroxy groups: ( S )HCCCH 2 NHCOCH(CH 3 )OH ( 1 ), ( S )HCCCH 2 NHCOCH(CH 3 )CH 2 OH ( 2 ), ( S )HCCCH 2 NHCOCH[CH(CH 3 ) 2 ]OH ( 3 ), ( S )HCCCH 2 NCOCH[CH 2 CH(CH 3 ) 2 ]OH ( 4 ), ( S )HCCCH 2 NHCOCH(C 6 H 5 )OH ( 5 ), and ( S )HCCCH 2 NHCOCH(CH 2 C 6 H 5 )OH ( 6 ) were synthesized and polymerized with [(nbd)RhCl] 2 –Et 3 N as a catalyst to obtain the corresponding polymers with moderate molecular weights ( $\overline M _{\rm n}$ = 8 400 to 32 000) in 45 to 86% yields. Polarimetric, circular dichroism (CD), and UV‐vis spectroscopic analyses revealed that poly( 1 ) and poly( 6 ) took a helical structure with, predominantly, a one‐handed screw sense. On the other hand, poly[( S )HCCCH 2 OCOCH(CH 3 )OH] [poly( 1′ )], an ester analogue of poly( 1 ), and poly( 2 )–poly( 5 ) did not take a predominantly one‐handed helical structure.