Anionic Polymerization of Novel Styrene Derivatives Bearing Various Amino Groups at ortho-Position

• Ajiro Hiroharu

  Department of Applied Chemistry, Graduate School of Engineering, Nagoya University

• Habaue Shigeki

  Department of Chemistry & Chemical Engineering, Faculty of Engineering, Yamagata University

• Okamoto Yoshio

  Department of Applied Chemistry, Graduate School of Engineering, Nagoya University

Abstract

The novel styrene derivatives bearing various amino groups at ortho-position, 2-(1-indolinyl)methylstyrene (2), 2-(9-carbazolyl)methylstyrene (3), 2-(N,N-diphenylamino)methylstyrene (4), 2-(N-3-methoxyphenyl-N-phenylamino)methylstyrene (5), and 2-(N-3-methylphenyl-N-phenylamino)methylstyrene (6), were synthesized and polymerized with radical and anionic initiations. As the bulkiness of the substituents at the ortho-position increased, the polymerizabilities of these monomers during the radical and anionic methods significantly decreased. The anionic polymerization of 4–6 with the n-butyllithium (−)-sparteine complex in toluene at 0 °C afforded the optically active polymers ([α]²⁵₃₆₅ +48° to +22°), whereas no optical activity was observed for the polymers of 2 and 3 obtained under the same conditions. The optically active polymers likely have a chiral helical conformation which is related to a high stereoregularity.

Journal

• Polymer Journal

  Polymer Journal 36 (4), 323-328, 2004

  The Society of Polymer Science, Japan

Keywords

• 2-(Aminomethyl)styrene
• Anionic Polymerization
• Stereoregularity
• Optically Active Polymer

Details

• CRID: 1390282681267246720
• NII Article ID: 130004430584
• NII Article ID: 10012886373
• NII Book ID: AA00777013
• DOI: 10.1295/polymj.36.323
• ISSN: 13490540
• ISSN: 00323896
• NDL BIB ID: 6912704
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I6912704
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed