Azobenzene-Based Macrocyclic Arenes: Synthesis, Crystal Structures, and Light-Controlled Molecular Encapsulation and Release
Yuezhou Liu
State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, 310027 P. R. China
These authors contributed equally to this work.
Search for more papers by this authorHongliang Wang
Department of Chemistry, Zhejiang University, Hangzhou, 310058 China
These authors contributed equally to this work.
Search for more papers by this authorPeiren Liu
State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, 310027 P. R. China
Search for more papers by this authorHuangtianzhi Zhu
State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, 310027 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Bingbing Shi
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, 730070 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xin Hong
Department of Chemistry, Zhejiang University, Hangzhou, 310058 China
State Key Laboratory of Clean Energy Utilization, Zhejiang University, Zheda Road 38, Hangzhou, 310027 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Feihe Huang
State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, 310027 P. R. China
Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou, 450001 P. R. China
Search for more papers by this authorYuezhou Liu
State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, 310027 P. R. China
These authors contributed equally to this work.
Search for more papers by this authorHongliang Wang
Department of Chemistry, Zhejiang University, Hangzhou, 310058 China
These authors contributed equally to this work.
Search for more papers by this authorPeiren Liu
State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, 310027 P. R. China
Search for more papers by this authorHuangtianzhi Zhu
State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, 310027 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Bingbing Shi
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, 730070 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xin Hong
Department of Chemistry, Zhejiang University, Hangzhou, 310058 China
State Key Laboratory of Clean Energy Utilization, Zhejiang University, Zheda Road 38, Hangzhou, 310027 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Feihe Huang
State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, 310027 P. R. China
Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou, 450001 P. R. China
Search for more papers by this authorAbstract
Azobenzene (azo)-based macrocycles are highly fascinating in supramolecular chemistry because of their light-responsiveness. In this work, a series of azo-based macrocyclic arenes 1, 2, 3, and 4, distinguished by the substituted positions of azo groups, is rationally designed and synthesized via a fragment-cyclization method. From the crystal and computed structures of 1, 2, and 3, we observe that the cavity size of these azo-macrocycles decreases gradually upon E→Z photoisomerization. Moreover, light-controlled host–guest complexations between azo-macrocycle 1 and guest molecules (7,7,8,8-tetracyanoquinodimethane, terephthalonitrile) are successfully achieved. This work provides a simple and effective method to prepare azo-macrocycles, and the light-responsive molecular-encapsulation systems in this work may further advance the design and applications of novel photo-responsive host–guest systems.
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