Convenient construction of unique bis-[1]rotaxanes based on azobenzene-bridged dipillar[5]arenes

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2021-10-25 DOI:10.1007/s10847-021-01115-0

Dan Li, Ying Han, Jing Sun, Wen-Long Liu, Chao-Guo Yan

引用次数: 4

Abstract

A series of azobenzene-bridged dipillar[5]arenes were conveniently synthesized by coupling reaction of aminoalkyl-functionalized pillar[5]arenes with azobenzene-4,4’-dioxyacetic acid or azobenzene-4,4’-dioxybutanoic acid in dry chloroform under the combinatorial catalysis of HOBt/EDCl. ¹H NMR, 2D NOESY spectra and single crystal structure clearly indicated that the unique bis-[1]rotaxanes could be formed by threading two diaminoalkylene units into the two cavities of pillar[5]arenes depending on the length of the diaminoalkylene chains. Under light irradiation at 365 nm, the trans-azobenzene unit transferred to cis-configuration, while the basic bis-[1]rotaxane structure was kept unchanged.

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基于偶氮苯桥联双柱[5]芳烃的独特双[1]轮烷的便捷构造

在HOBt/EDCl组合催化下，氨基烷基功能化柱[5]芳烃与偶氮苯-4,4′-二氧乙酸或偶氮苯-4,4′-二氧丁酸在干氯仿中偶联反应，方便地合成了一系列偶氮苯桥接双柱[5]芳烃。1H NMR、2D noesi光谱和单晶结构清楚地表明，根据二氨基亚烯链的长度，将两个二氨基亚烯单元插入柱状[5]芳烃的两个空腔中可以形成独特的双-[1]轮烷。在365 nm光照射下，反式偶氮苯单元转变为顺式构型，而基本的双-[1]轮烷结构保持不变。图形抽象

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来源期刊

Journal of Inclusion Phenomena and Macrocyclic Chemistry Agricultural and Biological Sciences-Food Science

CiteScore

4.10

自引率

8.70%

发文量

期刊介绍： The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.