Corralarenes: A Family of Conjugated Tubular HostsClick to copy article linkArticle link copied!
- Han HanHan HanCollege of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, ChinaDepartment of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United StatesMore by Han Han
- Rong FuRong FuCollege of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, ChinaMore by Rong Fu
- Ruiguo WangRuiguo WangCollege of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, ChinaMore by Ruiguo Wang
- Chun TangChun TangDepartment of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United StatesMore by Chun Tang
- Miao-Miao HeMiao-Miao HeCollege of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, ChinaMore by Miao-Miao He
- Jia-Ying DengJia-Ying DengCollege of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, ChinaMore by Jia-Ying Deng
- Dong-Sheng GuoDong-Sheng GuoCollege of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, ChinaMore by Dong-Sheng Guo
- J. Fraser StoddartJ. Fraser StoddartDepartment of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United StatesStoddart Institute of Molecular Science, Department of Chemistry, Zhejiang University, Hangzhou 310027, ChinaZJU-Hangzhou Global Scientific and Technological Innovation Center, Hangzhou 311215, ChinaSchool of Chemistry, University of New South Wales, Sydney 2052, NSW, AustraliaMore by J. Fraser Stoddart
- Kang Cai*Kang Cai*Email: [email protected]College of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, ChinaMore by Kang Cai
Abstract

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 103 to 107 M–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.
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