Synthesis of safranin O based semiconducting polytriazole by alkyne-azide click polymerization: an experimental and computational study
摘要
The alkyne-azide click polymerization method has been employed as a valuable approach for synthesizing useful polytriazoles. In this study, we report the synthesis of soluble, thermally stable, high-molecular-weight 1,4-regioregular polytriazole (PTA) based on safranin O and 4,4’-thiobisbenzenethiol (TBBT) monomers via click polymerization, utilizing the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) as a key step. The click approach was chosen for its high efficiency, atom economy, regioselectivity, and tolerance to a broad range of functional groups, allowing for the modular construction of polymeric architectures under mild reaction conditions. The synthesized polytriazole has been characterized using various spectroscopic techniques. Structural characterization data confirmed the successful formation of the polymer, while density functional theory (DFT) and time-dependent DFT (TD-DFT) analyses provided insights into the reaction kinetics and electronic structure. The band gap analysis indicated semiconducting behavior of the synthesized polymer. The developed polymer material exhibited excellent electrical properties, i.e., maximum conductivity of 3.77 × 10− 4 Scm− 1 at room temperature and activation energies of 2.5 × 10− 1 eV (before transition) and 1.3 × 10− 1 eV (after transition), and follows Arrhenius behavior. The rate constant for click polymerization determined by DFT was found to be 3.6 × 10− 27 cm3molecule− 1sec− 1.