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Photocontrolled chiral supramolecular assembly of azobenzene amphiphiles in aqueous media

Polymer Journal volume 55, pages 1189–1198 (2023)Cite this article

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Abstract

Supramolecular molecular amphiphiles that are photoresponsive have been intensively developed for a wide range of smart functional materials. As a photoswitch that displays high chemical and thermal stabilities, the azobenzene motif has been intensively incorporated into distinct soft materials to control properties and provide high temporal and high spatial resolution. However, only limited examples of molecular azobenzene amphiphiles (AAs) with chiral character have been reported with complicated synthetic manifold and photochemical studies. Herein, we design a novel molecular AA, AAPhe, with a simple molecular design and an L-amino acid motif. In addition to excellent photoresponsibility in organic media, AAPhe exhibits a high capacity for supramolecular transformation in aqueous media, as well as supramolecular chirality controlled by noninvasive photostimulation, as found in encouraging photochemical studies. Investigations of supramolecular behavior show that the supramolecular chiral structure induced by AAPhe assembles from microscopic to macroscopic length scales. The current design and studies of supramolecular assemblies of AAPhe provide us with fundamental concepts for constructing macroscopic functional materials with supramolecular chirality.

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Acknowledgements

This work was supported financially by the Croucher Foundation (Croucher Innovation Award-2021), The Hong Kong Polytechnic University (W08A, ZVST), and the Hong Kong Special Administrative Region Government (InnoHK). We acknowledge the technical support from UCEA and ULS of PolyU.

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  1. These authors contributed equally: Leong-Hung Cheung, Brian Boyan Liu

Authors and Affiliations

  1. State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong, China

    Leong-Hung Cheung, Brian Boyan Liu & Franco King-Chi Leung

  2. Centre for Eye and Vision Research, 17W Hong Kong Science Park, Hong Kong, China

    Franco King-Chi Leung

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Contributions

BBL performed all the synthesis and part of the characterization experiments for AAPhe. L-HC performed all characterizations of AAPhe in aqueous media, including TEM and SEM studies. FK-CL cowrote the paper and conceived and supervised the research. All authors discussed the results and commented on the manuscript.

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Correspondence to Franco King-Chi Leung.

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Cheung, LH., Liu, B.B. & Leung, F.KC. Photocontrolled chiral supramolecular assembly of azobenzene amphiphiles in aqueous media. Polym J 55, 1189–1198 (2023). https://doi.org/10.1038/s41428-023-00792-7

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