Issue 11, 2015
From the journal:

Polymer Chemistry

Ring-opening polymerization of a 2,3-disubstituted oxirane leading to a polyether having a carbonyl–aromatic π-stacked structure†

Maia Merlani,ab   Yasuhito Koyama,a   Hiroyasu Sato,c   Li Geng,a   Vakhtang Barbakadze,b   Bezhan Chankvetadzed  and  Tamaki Nakano*a  

* Corresponding authors

a Catalysis Research Center (CRC) and Graduate School of Chemical Sciences and Engineering, Hokkaido University, N 21, W 10, Kita-ku, Sapporo 001-0021, Japan
E-mail: tamaki.nakano@cat.hokudai.ac.jp
Fax: +81-11-7069156
Tel: +81-11-7069155

b Kutateladze Institute of Pharmacochemistry, Tbilisi State Medical University, 36 str. P. Sarajishvili, 0159 Tbilisi, Georgia

c Rigaku Corporation 4-14-4, Sendagaya, Shibuya-Ku, Tokyo 151-0051, Japan

d Department of Physical and Analytical Chemistry, School of Exact and Natural Sciences, Tbilisi State University, Chavchavadze Ave 1, 0179 Tbilisi, Georgia

Abstract

2-Methoxycarbonyl-3-(3,4-dimethoxyphenyl)oxirane was synthesized and polymerized using a cationic initiator to afford a polymer having a rather stiff, stretched conformation. The side-chain methoxycarbonyl group and 3,4-dimethoxyphenyl group of neighboring monomeric units may form a hetero π-stacked structure between side-chain carbonyl and aromatic groups which leads to intramolecular charge transfer (ICT) interactions. 2-Ethoxycarbonyl-3-phenyloxirane failed in polymerization, leading only to small molecules including cyclic compounds.

Graphical abstract: Ring-opening polymerization of a 2,3-disubstituted oxirane leading to a polyether having a carbonyl–aromatic π-stacked structure

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Article information

DOI
https://doi.org/10.1039/C4PY01711K
Article type
Communication
Submitted
10 Dec 2014
Accepted
13 Jan 2015
First published
16 Jan 2015

Polym. Chem., 2015,6, 1932-1936

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Ring-opening polymerization of a 2,3-disubstituted oxirane leading to a polyether having a carbonyl–aromatic π-stacked structure

M. Merlani, Y. Koyama, H. Sato, L. Geng, V. Barbakadze, B. Chankvetadze and T. Nakano, Polym. Chem., 2015, 6, 1932 DOI: 10.1039/C4PY01711K

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