Chain-Growth Polymerization of Benzotriazole Using Suzuki–Miyaura Cross-Coupling and Dialkylbiarylphosphine Palladium Catalysts
Michael Bautista, Anthony J. Varni, Josué Ayuso Carrillo, Chia‐Hua Tsai, Kevin J. T. Noonan
Abstract
Electron-deficient (n-type) conjugated materials are commonly prepared via step-growth methods with limited control over the molecular weight and molecular weight distribution of the resulting polymers. In this communication, we demonstrate that Pd-dialkylbiarylphosphine catalysts enable the chain-growth polymerization of benzo[1,2,3]triazole using Suzuki-Miyaura coupling with molecular weight control and modest molecular weight distributions (Đ ∼ 1.2–1.6). The importance of a free ligand in the reaction mixture during polymerization was established by analysis of polymer samples using GPC and MALDI-TOF mass spectrometry. A block copolymer with poly(3-hexylthiophene) was also synthesized by sequential monomer addition. The success of these commercially available catalysts for polymerization of benzotriazole highlights their potential for chain-growth reactions with other bicyclic arenes in the future.