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Pure Appl. Chem., 2010, Vol. 82, No. 4, pp. 1001-1009

Published online 2010-03-13

Click synthesis of donor–acceptor-type aromatic polymers

Tsuyoshi Michinobu

Global Edge Institute, Tokyo Institute of Technology, Ookayama, Meguro-ku, Tokyo 152-8550, Japan, and PRESTO, Japan Science and Technology Agency (JST), Kawaguchi, Saitama, Japan

Abstract: A high-yielding addition reaction between electron-rich alkynes and a small acceptor molecule, tetracyanoethylene (TCNE), was employed as a new click reaction to construct donor–acceptor chromophores in the polymer main chains and side chains. The donor–acceptor alternating conjugated polymers were prepared from the ferrocene-containing poly(aryleneethynylene)s in one step and atom-economic fashion. The energy levels and thermal properties of the aromatic polyamines substituted by electron-rich alkynes as a side chain can be tunable by the amount of the added TCNE. The resulting donor–acceptor-type polymers feature broad charge-transfer (CT) bands in the visible region, potent redox activities, and improved thermal properties.