Chiral oxazoline substituted optically active poly(m-phenylene)s: Synthesis and coupling polymerizations of (S)-4-benzyl-2-(3,5-dihalidephenyl) oxazoline using transition metal catalysts

Authors

  • Poompat Rattanatraicharoen,

    1. Department of Applied Chemistry, Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan
    Current affiliation:
    1. UBE Technical Center (Asia) Limited, 140/10 Moo 4 Tapong, Muang Rayong, Rayong 21000, Thailand
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  • Yoko Tanaka,

    1. Department of Applied Chemistry, Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan
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  • Keiko Shintaku,

    1. Department of Applied Chemistry, Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan
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  • Takuro Kawaguchi,

    1. Department of Applied Chemistry, Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan
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  • Kazuhiro Yamabuki,

    1. Department of Applied Chemistry, Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan
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  • Tsutomu Oishi,

    1. Department of Applied Chemistry, Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan
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  • Kenjiro Onimura

    Corresponding author
    1. Department of Applied Chemistry, Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan
    • Department of Applied Chemistry, Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan
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Abstract

Optically active poly(m-phenylene)s substituted with chiral oxazoline derivatives have been synthesized by the nickel-catalyzed Yamamoto coupling reaction of optically active (S)-4-benzyl-2-(3,5-dihalidephenyl)oxazoline derivatives (X = Br or I). The structures and chiroptical properties of the polymers were characterized by spectroscopic methods and thermal gravimetric analyses. The polymers showed higher absolute optical specific rotation values than their corresponding monomer, and showed a Cotton effect at transition region of conjugated main chain. The optical activities of the polymers should be attributed to the higher order structure such as helical conformations. Moreover, the helical conformation could be induced by addition of metal salts into polymer solutions. The polymers showed good thermal stabilities, which was attributable to the oxazoline side chains. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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