title: Application of alkyne-TCNQ addition reaction to polymerization.
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.
authors.affiliation: Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Washino
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Michinobu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000480:Alkynes; D009570:Nitriles; D011108:Polymers; C013703:tetracyanoquinodimethane