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Home  >  Journal list  >  Polymer Journal  >  Vol.27  No.6 (1995)  >  pp.579-590

Polymer Journal
<<Previous article Vol.27  No.6 (1995)   pp.579 - 590 Next article>>

Polymerization Reactivity and Chiroptical Property of N-Maleoyl-L-phenylalanine Cyclohexyl Ester

Kensoh Kagawa1) and Tsutomu Oishi1)
1) Department of Applied Chemistry and Chemical Engineering, Faculty of Engineering, Yamaguchi University

ABSTRACT:  A new type of optically active N-maleoyl-L-phenylalanine cyclohexyl ester (CHPAM) was synthesized from maleic anhydride, L-phenylalanine, and cyclohexanol. Radical and anionic polymerizations were carried out in several solvents at 60°C and 0°C, respectively, to obtain optically active polymers. Number average molecular weights (\barMn) of the homopolymers were 4.4×103 to 1.5×104. Specific optical rotations ([α]D) of the homopolymer were −69.7 to −65.9°. Radical copolymerizations of CHPAM (M1) were performed with styrene (ST, M2) or methyl methacrylate (MMA, M2) in benzene at 60°C. The monomer reactivity ratios (r1, r2) and Alfrey–Price Qe were determined as follows: r1=0.27, r2=0.11, Q1=2.00, e1=1.07 in the CHPAM–ST system; r1=0.07, r2=3.22, Q1=0.38, e1=1.63 in the CHPAM–MMA system. Circular dichroism (CD) spectra of the copolymers remarkably varied with increasing content of CHPAM. Relationships between [α]D and content (wt%) of CHPAM in the copolymer showed significant deviation from linearity. This suggests that asymmetric perturbation of the side chain chromophore and asymmetric induction in M1–M2 unit of the copolymer may occur.


Keyword:
Asymmetric Induction/ Asymmetric Perturbation/ N-Substituted Maleimide/ Styrene/ Methyl Methacrylate/ L-Phenylalanine Ester/ Optically Active Polymer

Published online: April 02, 2005
© Copyright, 2005 by The Society of Polymer Science, Japan

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