While functional macrocycles have been key platforms for supramolecular chemistry, preparing them in high yields on the multi-gram scale are challenging. Here, we present the creation of a C5-symmetric macrocycle, cyanostar, through a one-pot Knoevenagel condensation with high yields conducted on multi-gram scales. The central cavity is electropositive with CH hydrogen bonding units that are activated by electron-withdrawing cyano groups. In solution, the cyanostar shows high-affinity binding as 2:1 sandwich complexes, log �2 ~ 12, of large anions (BF4�, ClO4� and PF6�) usually considered �weakly coordinating�. The cyanostar's size preference allowed formation of an unprecedented [3]rotaxane templated around a dialkylphosphate. 

Cyanostars: Pentagonal macrocycles with cyanostilbene CH donors for binding anions and forming dialkylphosphate [3]rotaxanes

246th National Meeting (2013)

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