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Reversible isomerization of donor-acceptor Stenhouse adduct derivatives in water through dendritic confinement

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Abstract

Modulating reversible isomerization of hydrophobic dyes in aqueous solutions is greatly desired. Here we report on reversible isomerization of solvatochromic donor-acceptor Stenhouse adducts (DASAs) in water through the confinement from dendritic oligoethylene glycols (OEGs). Dendronization of DASAs with dendritic OEGs affords them characteristic thermoresponsiveness. These dendronized DASAs spontaneously isomerize in water from hydrophobic linear state into hydrophilic cyclic state at room temperature due to the strong hydration. However, hydrophobic microenvironment through thermally dehydration and collapse of the dendritic OEGs at elevated temperatures confines hydration of the DASA moieties and mediates their interactions with the collapsed hydrophobic OEG domains, affording their isomerization recovery in water efficiently from the hydrophilic cyclic state into the hydrophobic linear state. The confinement-mediated reversible isomerization of DASA moieties in water can be repeated through alternative photo-irradiation and thermal dehydrations, exhibiting excellent fatigue resistance.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21971160, 21971161, 22271183 and 22371179) and the Program for Professor of Special Appointment (Eastern Scholar TP2019039) at Shanghai Institutions of Higher Learning.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. International Joint Laboratory of Biomimetic and Smart Polymers, School of Materials Science and Engineering, Shanghai University, Shanghai, 200444, China

    Jiaxing Zhang, Qingyun Zhao, Xinyan Su, Afang Zhang & Wen Li

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  1. Jiaxing Zhang
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  2. Qingyun Zhao
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  3. Xinyan Su
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  4. Afang Zhang
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Correspondence to Xinyan Su, Afang Zhang or Wen Li.

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Supporting information The supporting information is available online at chem.scichina.com and link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Zhang, J., Zhao, Q., Su, X. et al. Reversible isomerization of donor-acceptor Stenhouse adduct derivatives in water through dendritic confinement. Sci. China Chem. 67, 1636–1646 (2024). https://doi.org/10.1007/s11426-023-1959-x

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