A new hexaaza bicyclic cyclophane with dual binding sites

Abstract

A new C₃-symmetric drum-shaped homoditopic haxaamino bicyclic cyclophane and its hexachloride and hexaiodide complexes have been synthesized and characterized and dual recognition of guests has been demonstrated. Single-crystal X-ray analysis illustrates that bicyclic cyclophane has a cavity and side pockets for acetone molecules. The hexaprotonated state of this bicycle shows encapsulation of an iodide inside its cavity, and in hexachloride complex, chloride is recognized as Cl^-···H₂O in each of the three side pockets which are in extensive hydrogen bonding interactions with the water and chlorides. ¹H NMR experiments have also been carried out on hexatosylated cyclophane with the halides to study solution state binding.