A pillar[5]arene and crown ether fused bicyclic host: synthesis, guest discrimination and simultaneous binding of two guests with different shapes, sizes and electronic constitutions

Wei-Bo Hu; Hong-Mei Yang; Wen-Jing Hu; Ming-Liang Ma; Xiao-Li Zhao; Xian-Qiang Mi; Yahu A. Liu; Jiu-Sheng Li; Biao Jiang; Ke Wen

doi:10.1039/C4CC01810A

A pillar[5]arene and crown ether fused bicyclic host: synthesis, guest discrimination and simultaneous binding of two guests with different shapes, sizes and electronic constitutions†

Wei-Bo Hu,^a Hong-Mei Yang,^a Wen-Jing Hu,^b Ming-Liang Ma,*^a Xiao-Li Zhao,^c Xian-Qiang Mi,^b Yahu A. Liu,^d Jiu-Sheng Li,*^b Biao Jiang*^b and Ke Wen*^abe

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* Corresponding authors

^a Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China
E-mail: kwen@brain.ecnu.edu.cn, mlma@brain.ecnu.edu.cn

^b Shanghai Advanced Research Institute, Chinese Academy of Science, Shanghai 201210, China
E-mail: lijs@sari.ac.cn, jiangb@sari.ac.cn, wenk@sari.ac.cn

^c Shanghai Key Laboratory of Green Chemistry and Chemical Processes, and Department of Chemistry, East China Normal University, Shanghai 200062, China

^d Medicinal Chemistry, ChemBridge Research Laboratories Inc., San Diego, USA

^e School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China

Abstract

A bicyclic host molecule 1 consisting of a pillar[5]arene and a 1,5-dioxynaphthalene-based crown ether unit has been synthesized, and the two cyclic subunits in 1 were found to recognize two different guest molecules (1,4-dicyanobutane and paraquat) selectively or take up the two guest molecules simultaneously.

Chemical Communications

A pillar[5]arene and crown ether fused bicyclic host: synthesis, guest discrimination and simultaneous binding of two guests with different shapes, sizes and electronic constitutions†

Abstract

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A pillar[5]arene and crown ether fused bicyclic host: synthesis, guest discrimination and simultaneous binding of two guests with different shapes, sizes and electronic constitutions

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