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Light-Triggered Self-Assembly of a Spiropyran-Functionalized Dendron into Nano-/Micrometer-Sized Particles and Photoresponsive Organogel with Switchable Fluorescence

Authors

  • Qun Chen,

    1. Beijing National Laboratory for Molecular Sciences CAS Key Laboratories of Organic Solids and Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences Beijing 100190 (PR China)
    2. Graduate School of Chinese Academy of Sciences Beijing 100190 (PR China)
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  • Yu Feng,

    1. Beijing National Laboratory for Molecular Sciences CAS Key Laboratories of Organic Solids and Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences Beijing 100190 (PR China)
    2. Graduate School of Chinese Academy of Sciences Beijing 100190 (PR China)
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  • Deqing Zhang,

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences CAS Key Laboratories of Organic Solids and Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences Beijing 100190 (PR China)
    • Beijing National Laboratory for Molecular Sciences CAS Key Laboratories of Organic Solids and Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences Beijing 100190 (PR China).
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  • Guanxin Zhang,

    1. Beijing National Laboratory for Molecular Sciences CAS Key Laboratories of Organic Solids and Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences Beijing 100190 (PR China)
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  • Qinghua Fan,

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences CAS Key Laboratories of Organic Solids and Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences Beijing 100190 (PR China)
    • Beijing National Laboratory for Molecular Sciences CAS Key Laboratories of Organic Solids and Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences Beijing 100190 (PR China).
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  • Shuna Sun,

    1. Beijing National Laboratory for Molecular Sciences CAS Key Laboratories of Organic Solids and Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences Beijing 100190 (PR China)
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  • Daoben Zhu

    1. Beijing National Laboratory for Molecular Sciences CAS Key Laboratories of Organic Solids and Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences Beijing 100190 (PR China)
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Abstract

The synthesis, self-assembly, and spectroscopic investigations of spiropyran (SP)-functionalized dendron 1 are reported. Under UV light irradiation, assembly of 1 into nano-/microparticles occurs due to the transformation of the closed form of SP into the open merocyanine (MC) form. The formation of these nano-/microparticles is confirmed by transmission electron microscopy (TEM) and dynamic light scattering (DLS) experiments in addition to the confocal laser scanning microscopy (CLSM) measurements. These nano-/microparticles exhibit relatively strong red emission. It is interesting to note that the direct cooling of the toluene/benzene solution of 1 to 0 °C leads to gel formation. Multivalent π–π interactions due to the dendron in 1 may be the driving-force for the gelation. The UV light irradiation cannot destroy the gel phase, and in fact, the gel–gel transition is successfully realized. The purple-blue gel exhibits relatively strong red fluorescence; moreover, the fluorescence can be reversibly switched by alternating UV and visible light irradiation. The results clearly indicate that the MC form after aggregation becomes more stable and fluorescent.

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