An ionic polyacetylene derivative with the N-[(triethylene glycol)methyl ether]pyridinium tosylate

Abstract

ABSTRACTThe non-catalyst polymerization of 2-ethynylpyridine using tri(ethylene glycol)methyl ether tosylate yielded an ionic polyacetylene with the N-[(triethylene glycol)methyl ether]pyridinium tosylate substituents. The polymerization proceeded well in homogeneous manner to give the resulting poly{2-ethynyl-N[(triethylene glycol)methyl ether]pyridinium tosylate} in moderate yield. The polymer was completely soluble in such organic solvents as methanol, DMF, DMSO, NMP including water. The chemical structure of the resulting polymer was characterized by such instrumental methods as IR, NMR, and UV-visible spectroscopies to have the conjugated backbone system with the N-[(triethylene glycol)methyl ether]pyridinium tosylate. The absorption spectrum starts around 600 nm, which is due to the π→ π* interband transition of conjugated polymer system. HOMO and LUMO level were 5.46 and 3.39 eV. The electrochemical properties of polymer was also measured. This polymer exhibited initial onset voltage of 0.73 V for oxidation and stable redox property up to 50 cycles.