Corralarenes: A Family of Conjugated Tubular Hosts

Han Han, Rong Fu, Ruiguo Wang, Chun Tang, Miao Miao He, Jia Ying Deng, Dong Sheng Guo, J. Fraser Stoddart, Kang Cai*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


Despite the advances in host-guest chemistry, macrocyclic hosts with deep cavities are far from abundant among the large number of wholly synthetic hosts described in the literature. Herein, we describe the design and synthesis of two new tubular hosts, namely, corral[4]arene and corral[5]arene. The former has been isolated and characterized as two conformational diastereoisomers, one is centrosymmetric and the other asymmetric. The latter, a fivefold symmetrical and flexible host, has also been investigated in detail. It is composed of five 4,4′-dimethoxybiphenyl units bridged by ethynylene linkers at their 2,2′-positions and adopts a pentagonal conformation with a tubular-shaped cavity in the presence of guests. This structure endows corral[5]arene not only with a conjugated backbone, capable of bright fluorescent emission (quantum yield, 56%), but also a deep π-electron-rich aromatic cavity with remarkable conformational flexibility. The adaptive cavity of corral[5]arene allows it to accommodate a wide range of neutral and positively charged electron-deficient guests with different molecular sizes and shapes. Binding constants between this host and these guests in three different nonpolar organic solvents lie in the range of 103to 107M-1. Moreover, corral[5]arene exhibits dynamic chirality on account of the axes of chirality associated with each of the five biphenyl units and displays first-order transformation as exhibited by circular dichroism in response to the addition of chiral guests. All these stereochemical features render corral[5]arene an attractive host for a variety of supramolecular and nanotechnological applications.

Original languageEnglish (US)
Pages (from-to)20351-20362
Number of pages12
JournalJournal of the American Chemical Society
Issue number44
StatePublished - Nov 9 2022

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry


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