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Updated: Jun 2, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Application of alkyne-TCNQ addition reaction to polymerization
Yusuke Washino1, Tsuyoshi Michinobu
1Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.
Abstract:
The polymerization using a high-yielding addition reaction between electron-rich alkynes and 7,7,8,8-tetracyanoquinodimethane (TCNQ) derivatives is described. The bifunctional monomer containing two TCNQ moieties and the counter comonomer bearing two dialkylaniline (DAA)-substituted alkynes are reacted in 1,2-dichloroethane under mild heating conditions. At the high monomer concentrations, high molecular weight linear polymers are obtained, while the reaction at the low monomer concentrations produces a significant amount of the cyclic compounds. A clear relationship between the monomer concentration and the cyclic compound amount is demonstrated. The obtained polymers feature a sufficient thermal stability with the decomposition temperature exceeding 300 °C as well as strong charge-transfer (CT) bands and redox activities ascribed to the produced donor-acceptor moieties. These features are also used to optimize the polymerization conditions and to estimate the chemical structures.
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