A %26apos;clicked%26apos; macrocyclic probe incorporating Binol as the signalling unit for the chiroptical sensing of anions

作者：Caricato Marco; Olmo Alessandro; Gargiulli Claudia; Gattuso Giuseppe; Pasini Dario^*

来源：Tetrahedron, 2012, 68(38): 7861-7866.

DOI：10.1016/j.tet.2012.07.038

• Circular dichroism
• Macrocycles
• Click chemistry
• Anion binding
• Sensors

We describe a macrocyclic chiroptical sensor for the detection of halide anions, with the Binol moiety acting as the CD signalling unit. The macrocycle is conveniently synthesized using CuAAC %26apos;click%26apos; reactions in the cyclization step; this methodology installs 1,2,3-triazole moieties within the macrocyclic backbone, able to directionally bind anions by means of CH center dot center dot center dot X- hydrogen bonds. H-1 NMR complexation studies in CDCl3 reveal weak binding to halide and aliphatic carboxylate anions. Halide anions, however, when held into the macrocyclic cavity, are able to trigger a large chiroptical response originating from the steric interaction with the Binol moiety, which changes its dihedral angle, thus modulating its characteristic CD signature.