| Summary: | Here, we report the synthesis and thermophysical properties of seven primarily aromatic, imidazolium-based polyamide ionenes. The effects of varied <i>para</i>-, <i>meta</i>-, and <i>ortho</i>-connectivity, and spacing of ionic and amide functional groups, on structural and thermophysical properties were analyzed. Suitable, robust derivatives were cast into thin films, neat, or with stoichiometric equivalents of the ionic liquid (IL) 1-benzy-3-methylimidazolium bistriflimide ([Bnmim][Tf<sub>2</sub>N]), and the gas transport properties of these membranes were measured. Pure gas permeabilities and permselectivities for N<sub>2</sub>, CH<sub>4</sub>, and CO<sub>2</sub> are reported. Consistent <i>para</i>-connectivity in the backbone was shown to yield the highest CO<sub>2</sub> permeability and suitability for casting as a very thin, flexible film. Derivatives containing terephthalamide segments exhibited the highest CO<sub>2</sub>/CH<sub>4</sub> and CO<sub>2</sub>/N<sub>2</sub> selectivities, yet CO<sub>2</sub> permeability decreased with further deviation from consistent <i>para</i>-linkages.
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