Tailoring Pore Size and Chemical Interior of near 1 nm Sized Pores in a Nanoporous Polymer Based on a Discotic Liquid Crystal

A triazine based disc shaped molecule with two hydrolyzable units, imine and ester groups, was polymerized via acyclic diene metathesis in the columnar hexagonal (Col(hex)) LC phase. Fabrication of a cationic nanoporous polymer (pore diameter similar to 1.3 nm) lined with ammonium groups at the pore surface was achieved by hydrolysis of the imine linkage. Size selective aldehyde uptake by the cationic porous polymer was demonstrated. The anilinium groups in the pores were converted to azide as well as phenyl groups by further chemical treatment, leading to porous polymers with neutral functional groups in the pores. The pores were enlarged by further hydrolysis of the ester groups to create similar to 2.6 nm pores lined with -COONa surface groups. The same pores could be obtained in a single step without first hydrolyzing the imine linkage. XRD studies demonstrated that the Col(hex) order of the monomer was preserved after polymerization as well as in both the nanoporous polymers. The porous anionic polymer lined with -COOH groups was further converted to the -COOLi, -COONa, -COOK, -COOCs, and -COONH4 salts. The porous polymer lined with -COONa groups selectively adsorbs a cationic dye, methylene blue, over an anionic dye.