A light-operated pillar[6]arene-based molecular shuttle

Tomoki Ogoshi; Daisuke Kotera; Shixin Fa; Shungo Nishida; Takahiro Kakuta; Tada-Aki Yamagishi; Albert M Brouwer

doi:10.1039/d0cc03945d

A light-operated pillar[6]arene-based molecular shuttle

Chem Commun (Camb). 2020 Sep 17;56(74):10871-10874. doi: 10.1039/d0cc03945d.

Authors

Tomoki Ogoshi¹, Daisuke Kotera², Shixin Fa³, Shungo Nishida², Takahiro Kakuta⁴, Tada-Aki Yamagishi², Albert M Brouwer⁵

Affiliations

¹ Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan. ogoshi@sbchem.kyoto-u.ac.jp and WPI Nano Life Science Institute, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
² Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
³ Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan. ogoshi@sbchem.kyoto-u.ac.jp.
⁴ WPI Nano Life Science Institute, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan and Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
⁵ van't Hoff Institute for Molecular Sciences, University of Amsterdam, P.O. Box 94157, 1090 GD Amsterdam, The Netherlands.

PMID: 32789406
DOI: 10.1039/d0cc03945d

Abstract

A molecular shuttle comprising a pillar[6]arene macrocyclic ring and an axle with two equal-energy-level stations connected by an azobenzene unit was synthesised. The E isomer of the azobenzene functioned as "open gate", allowing the pillar[6]arene ring to rapidly shuttle back-and-forth between the two stations. Ultraviolet irradiation induced photo-isomerisation of the azobenzene from E to Z form. The Z isomer of the azobenzene functioned as a "closed gate", inhibiting shuttling of the pillar[6]arene ring.