Synthesis of poly(p-phenyleneethynylene)s bearing oligo-ethylene glycols and their gas permeation properties

1,4-Diiodobenzenes bearing oligo-ethylene glycols [IRC6H2IR, R = OCH2CH2OCH3 (1a), O(CH2CH2O)2CH3 (1b), O(CH2CH2O)3CH3 (1c)] were polymerized with 1,4-diethynylbenzene in the presence of Pd/Cu catalyst to afford poly(p-phenyleneethynylene)s bearing oligo-ethylene glycols (2a–c), respectively. Polymer 2a was insoluble in any solvents, but the other polymers (2b, 2c) were soluble in CHCl3. The weight-average molecular weights of 2b and 2c were 5.4 × 104 and 9.6 × 104, respectively, and they gave free-standing membranes by solution-casting method. The densities of membranes of 2b and 2c were 1.26 and 1.22 g/cm3, respectively, and their carbon dioxide permeability coefficients were 12.9 and 13.5 barrers, respectively. The CO2/N2 separation factor of membrane of 2b was as large as 33.7. Membrane of 3b, which contains triethylene glycols, exhibited higher CO2 permselectivity, and the CO2/N2 separation factor was 50.0.