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

Abstract

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.

Keywords:

• Sulfonamidocarbazole
• dipyrromethane
• macrocyclic receptor
• anion recognition