Chain-Growth Polymerization of Benzotriazole Using Suzuki–Miyaura Cross-Coupling and Dialkylbiarylphosphine Palladium Catalysts

• DOI: 10.1021/acsmacrolett.0c00580
• Publication Date: 2020-08-28T18:57:25Z
• Authors: Michael V. Bautista; Anthony J. Varni; Josué Ayuso-Carrillo; Chia-Hua Tsai; Kevin J. T. Noonan
• Keywords: 02 engineering and technology; 0210 nano-technology

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.