Pendant structure governed anion sensing property for sulfonamide-functionalized poly(phenylacetylene)s bearing various α-amino acids

Authors

  • Ryohei Kakuchi,

    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan
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  • Ryotaro Shimada,

    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan
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  • Yasuyuki Tago,

    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan
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  • Ryosuke Sakai,

    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan
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  • Toshifumi Satoh,

    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan
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  • Toyoji Kakuchi

    Corresponding author
    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan
    • Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan
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Abstract

The colorimetric detection of anionic species has been studied for α-amino acid-conjugated poly(phenylacetylene)s, which were prepared by the polymerization of the ethyl esters of N-(4-ethynylphenylsulfonyl)-L-alanine, L-isoleucine, L-valine, L-phenylalanine, L-aspartic acid, and L-glutamic acid using Rh+(2,5-norbornadiene)[(η6-C6H5)B(C6H5)3] as the catalyst in CHCl3. The one-handed helical conformations of all the sulfonamide-functionalized polymers were characterized by Cotton effects in the circular dichroism spectra. The addition of anions with a relatively high basicity, such as tetra-n-butylammonium acetate and fluoride, induced drastic changes in both the optical and chiroptical properties. On the other hand, anions with a relatively low basicity, such as tetra-n-butylammonium nitrate, azide, and bromide, had essentially no effects on the helical conformation of all the sulfonamide-functionalized polymers. The anion signaling property of the sulfonamide-functionalized polymers possessing α-amino acid moieties was significantly affected by the installed residual amino acid structures. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 1683–1689, 2010

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