A Versatile Method for Adjusting Thermoresponsivity: Synthesis and ‘Click’ Reaction of an Azido End-Functionalized Poly(N-isopropylacrylamide)

Authors

  • Atsushi Narumi,

    1. Department of Polymer Science and Engineering, Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa 992-8510, Japan
    Search for more papers by this author
  • Keita Fuchise,

    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, N13 W8, Kita-ku, Sapporo 060-8628, Japan
    Search for more papers by this author
  • Ryohei Kakuchi,

    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, N13 W8, Kita-ku, Sapporo 060-8628, Japan
    Search for more papers by this author
  • Atsushi Toda,

    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, N13 W8, Kita-ku, Sapporo 060-8628, Japan
    Search for more papers by this author
  • Toshifumi Satoh,

    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, N13 W8, Kita-ku, Sapporo 060-8628, Japan
    Search for more papers by this author
  • Seigou Kawaguchi,

    1. Department of Polymer Science and Engineering, Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa 992-8510, Japan
    Search for more papers by this author
  • Kenji Sugiyama,

    1. Polymeric and Organic Materials Department, Graduate School of Science and Engineering, Tokyo Institute of Technology H-127, 2-12-1, Ohokayama, Meguro-ku, Tokyo 152-8552, Japan
    Search for more papers by this author
  • Akira Hirao,

    1. Polymeric and Organic Materials Department, Graduate School of Science and Engineering, Tokyo Institute of Technology H-127, 2-12-1, Ohokayama, Meguro-ku, Tokyo 152-8552, Japan
    Search for more papers by this author
  • Toyoji Kakuchi

    Corresponding author
    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, N13 W8, Kita-ku, Sapporo 060-8628, Japan
    • Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, N13 W8, Kita-ku, Sapporo 060-8628, Japan.
    Search for more papers by this author

Abstract

The 2-chloropropionamide derivative featuring an azido group is used as the initiator for the ATRP of N-isopropylacrylamide (NIPAM) with copper(I) chloride (CuCl) and tris[2-(dimethylamino)ethyl]amine (Me6TREN) to produce the PNIPAM end-functionalized with an azido group. Subsequently, the ‘click’ reaction between the azido end-group and acetylene derivatives is demonstrated to produce PNIPAM in which the end-groups are modified by the phenyl, 4-phenoxyphenyl, butyl, octyl, carboxylic acid, and hydroxymethyl groups. The resulting PNIPAM derivatives show a LCST that ranges from 34.8 to 44.6 °C depending on the introduced end-group.

original image

Ancillary