Syntheses and properties of meso-substituted porphyrin mesogens with triazole linkages and peripheral alkyl chains.

Discotic mesogens P/n-M (n=12, 16, 18, M=2H, Zn and Cu) bearing a porphyrin core, triazole linkages and peripheral 3,4,5-trialkoxybenzyl units have been synthesized by a click-chemistry approach. The thermal behavior, photophysical properties and morphologies of these compounds were investigated by polarized optical microscopy (POM), differential scanning calorimetry (DSC), XRD, UV and PL, SEM and TEM. These compounds can self-assemble into hexagonal columnar phases in their pure states and form organogels in 1,4-dioxane with unusually flower-like sphere morphology. The supramolecular complexes of P/18-Zn with C-70 or 4,7-di-4-pydriyl-2,1,3-benzothadiazole can display hexagonal columnar phases too. Additionally, zinc porphyrin compounds P/n-Zn show binding selectivity to Cu2+ among a series of cations in THF/H2O.