Synthesis and anion binding properties of 1,8-disulfonamidocarbazole dipyrromethane Schiff-base macrocycle & its amine analogue

2015-11-18T00:00:00Z (GMT) by Feng Zhang Yu-hui Zhou Xiao-ping Bao

A novel 1,8-disulfonamidocarbazole-dipyrromethane Schiff-base macrocycle (1) and its amine analogue (2) were designed and synthesised, and their anion binding properties were studied via UV–vis and 1H NMR titration spectra. The obtained results showed that a small change in the macrocyclic structure (by reducing imines into the corresponding amines) produced a remarkable impact on its binding affinity and selectivity for anions. For example, macrocycle 1 displayed a 7.9:1 F/H2PO4 selectivity; however, its amine analogue 2 showed a 78.5:1 F/H2PO4 selectivity.