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

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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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Acknowledgements

We are grateful to the financial support by the National Natural Science Foundation of China (Grant No. 21871227) and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

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This study was funded by National Natural Science Foundation of China (21871227).

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  1. College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, 225002, China

    Dan Li, Ying Han, **g Sun, Wen-Long Liu & Chao-Guo Yan

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Li, D., Han, Y., Sun, J. et al. Convenient construction of unique bis-[1]rotaxanes based on azobenzene-bridged dipillar[5]arenes. J Incl Phenom Macrocycl Chem 102, 261–270 (2022). https://doi.org/10.1007/s10847-021-01115-0

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