Tetraphenylene triazolophanes have demonstrated many hallmark lessons of supramolecular chemistry in receptor design for the size-selective binding of chloride.  Taking advantage of its shape-persistence, we aimed to tune its selectivity by installing flanking 1,8-naphthalimide spacers to create a new class of triazolophanes with elliptical cavities (MC , X = CH) for enhanced binding of linear anions (i.e. N3�, SCN�).  The stepwise and modular synthesis of these macrocycles also allowed for the systematic installation of pyridyl head groups (X = N) by which its internally directed dipole was found to promote formation of sandwich complexes around tetrahedral anions (i.e., ClO4�) with high binding affinities (�2 ~ 1012 M�1).

Tunable selectivity in expanded, shape persistent-triazolophanes

246th National Meeting (2013)

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