Azobenzene‐Based Macrocyclic Arenes: Synthesis, Crystal Structures, and Light‐Controlled Molecular Encapsulation and Release. Issue 11 (26th January 2021)

• Record Type: Journal Article
• Authors: Liu, Yuezhou; Wang, Hongliang; Liu, Peiren; Zhu, Huangtianzhi; Shi, Bingbing; Hong, Xin; Huang, Feihe
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 11(2021)
• Page Start: 5766
• Page End: 5770
• Publication Date: 2021-01-26
• Subjects: host–guest systems -- light-responsiveness -- macrocycles -- photochemistry -- supramolecular chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202015597
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : A series of azobenzene‐based macrocyclic arenes 1, 2 and 3 is synthesized. Light‐controlled molecular encapsulation and release are realized based on macrocycle 1 .