Get access

Chirality responsive helical poly(phenylacetylene) bearing L-proline pendants

Authors

  • Hiroaki Kawamura,

    1. Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan Contribution to the Proceedings of the 22nd International Symposium on Chirality [ISCD 22]
    Search for more papers by this author
  • Yoshihisa Takeyama,

    1. Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan Contribution to the Proceedings of the 22nd International Symposium on Chirality [ISCD 22]
    Search for more papers by this author
  • Miho Yamamoto,

    1. Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan Contribution to the Proceedings of the 22nd International Symposium on Chirality [ISCD 22]
    Search for more papers by this author
  • Hiroyuki Kurihara,

    1. Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan Contribution to the Proceedings of the 22nd International Symposium on Chirality [ISCD 22]
    Search for more papers by this author
  • Kazuhide Morino,

    1. Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan Contribution to the Proceedings of the 22nd International Symposium on Chirality [ISCD 22]
    Current affiliation:
    1. Molecular Engineering Institute, Kinki University, Kayanomori, Iizuka, Fukuoka 820-8555, Japan
    Search for more papers by this author
  • Eiji Yashima

    Corresponding author
    1. Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan Contribution to the Proceedings of the 22nd International Symposium on Chirality [ISCD 22]
    • Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan

    Search for more papers by this author

  • Tang et al. and Masuda et al. synthesized helical poly(phenylacetylene)s and poly(N-propargylamide) bearing various amino acids as the pendants, respectively, and their chiroptical properties including their helical conformations and helicity inversion were investigated.

  • An L-proline-bound polyacetylene has been prepared, but its homopolymer was reported to exist as a non-helical conformation.

Abstract

A novel, optically active, cis-transoidal poly(phenylacetylene) bearing an L-proline residue as the pendant group () was prepared by the polymerization of the corresponding monomer using a rhodium catalyst in water, and its chiroptical property was investigated using circular dichroism spectroscopy. showed intense Cotton effects in the UV–visible region of the polymer backbone in water, resulting from the prevailing one-handed helical conformation induced by the covalent-bonded chiral L-proline pendants and exhibited a unique helix-sense inversion in response to external, achiral, and chiral stimuli, such as the solvent and interactions with chiral small molecules. We found that could enantioselectively trap 1,1′-2-binaphthol within its hydrophobic helical cavity inside the polymer in aqueous media and underwent an inversion of its helical sense in the presence of one of the enantiomers. The effect of the optical purity of 1,1′-2-binaphthol on the chiroptical properties of was also investigated. Chirality 23:35–42, 2011 © 2011 Wiley Periodicals, Inc.

Ancillary