Cyclophane-Sustained Ultrastable Porphyrins

• DOI: 10.1021/jacs.0c02311
• Publication Date: 2020-04-03T17:32:06Z
• Authors: Wenqi Liu; Chenjian Lin; Jacob A. Weber; Charlotte L. Stern; Ryan M. Young; Michael R. Wasiel...; J. Fraser Stoddart
• Keywords: Cyclophane; Affinities; Free base; Supermolecule; Solvolysis

We report the encapsulation of free-base and zinc porphyrins by a tricyclic cyclophane receptor with subnanomolar binding affinities in water. The high are sustained hydrophobic effect multiple [CH···π] interactions covering large [π···π] stacking surfaces between substrate receptor. discovered two co-conformational isomers 1:1 complex, where porphyrin is orientated differently inside cavity on account its nature. photophysical properties chemical reactivities encapsulated modulated to considerable extent Improved fluorescence quantum yields, red-shifted absorptions emissions, nearly quantitative energy transfer processes highlight emergent enhancements. enjoy unprecedented stabilities, their D/H exchange, protonation, solvolysis under extremely acidic conditions completely blocked. anticipate that ultrahigh stabilities improved optical these will find applications single-molecule materials, artificial photodevices, biomedical appliances.