Despite the advances in host-guest chemistry, macrocyclic hosts with deep cavities are far from abundant among the large number of wholly synthetic macrocycles described in the literatures. Herein, a new five-fold symmetrical host—namely, corral[5]arene—has been designed and synthesized. It is composed of five 4,4′-dimethoxy biphenyl units bridged by ethynylene linkers at their 2,2′-positions and adopts a pentagonal conformation with a tubular-shaped cavity. This structure endows corral[5]arene, not only with a conjugated backbone capable of bright fluorescent emission, but also a deep, π-electron-rich aromatic cavity with remarkable conformational flexibility. The deep and adaptive cavity of corral[5]arene allows it to accommodate a wide range of neutral and positively charged electron-deficient guests with differing molecular sizes and shapes. Binding constants with this host with these guests in three different organic solvents lie in the range of 103 to 107 M−1. Moreover, corral[5]arene exhibits chirality on account of the chiral axes associated with five biphenyl units and displays first-order transformation as exhibited by circular dichroism in response to chiral guests. All these stereochemical features render corral[5]arene an attractive host for a variety of supramolecular and nanotechnological applications.

Corral[5]arene: a deep-cavity host for adaptive guest inclusion

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