Green-Light-Triggered Phase Transition of Azobenzene Derivatives toward Reversible Adhesives

Wu, Zhen; Ji, Chendong; Zhao, Xujie; Han, Yilong; Müllen, Kläus; Pan, Kai; Yin, Meizhen

doi:10.1021/jacs.9b01056

Cited by 132 publications

(129 citation statements)

References 32 publications

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“…Moreover, we also measured the fluorescence lifetimes of above six samples. Using the absolute quantum yield and fluorescence lifetime, we calculated the radiative constant rate ( k r ) and nonradiative constant rate ( k nr ) of above six samples . We found that the k nr / k r ratio of the fluorophore Cypate in 1‐NPs (i.e., simultaneous intra‐ and intermolecular quenching, k nr / k r = 997.8) is much larger than that in either 1‐Dimer (i.e., intramolecular quenching, k nr / k r = 15.7) or 1‐Fmoc‐NPs (i.e., intermolecular quenching, k nr / k r = 499.3) (Table.…”

Section: Resultsmentioning

confidence: 99%

Increasing Photothermal Efficacy by Simultaneous Intra‐ and Intermolecular Fluorescence Quenching

Chong

Hu³

et al. 2019

Adv Funct Materials

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Recently, using in situ self-assembly-induced fluorescence quenching (i.e., intermolecular quenching denoted herein) of a photothermal agent (PTA) to enhance its photothermal efficiency has proven to be a successful photothermal therapy (PTT) strategy. But to the best of current knowledge, using simultaneous intra-and intermolecular fluorescence quenching of a PTA to additionally increase its photothermal efficacy has not been reported. Herein, employing a click condensation reaction and a rationally designed PTA Biotin-Cystamine-Cys-Lys(Cypate)-CBT (1), a "smart" strategy is developed of intracellular simultaneous intra-and intermolecular fluorescence quenching and applied it to largely increase the photothermal efficacy of the agent both in vitro and in vivo. After being internalized by biotin receptor-overexpressing cancer cells, 1 is reduced by intracellular glutathione to initiate a CBT-Cys condensation reaction (intramolecular quenching) and self-assembly (intermolecular quenching) to form the nanoparticles 1-NPs (simultaneous intra-and intermolecular fluorescence quenching). Experimental results indicate that 1-NPs have higher fluorescence quenching efficiency than the control PTAs [Thiazole-Lys(Cypate)-Benzothiazole] 2 (1-Dimer, intramolecular quenching), and nanoparticles of Cystamine-Cys(Fmoc)-Lys(Cypate)-CBT (1-Fmoc-NPs, intermolecular quenching). It is envisioned that, by replacing the biotin group on 1 with other targeting warheads, the "smart" strategy is ready to increase the photothermal therapeutic efficiency of their corresponding diseases.

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Section: Resultsmentioning

confidence: 99%

Increasing Photothermal Efficacy by Simultaneous Intra‐ and Intermolecular Fluorescence Quenching

Chong

Hu³

et al. 2019

Adv Funct Materials

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“…Second, Yin'sgroup reported the phase transition of azobenzene-containing compounds by photothermal effect based on the adsorption of visible light. [25] It avoidedt he drawbacks of UV light irradiation, such as low penetration and light-induced damageso fm aterials. Visible-light-controlled solid-to-liquid transitions are necessary, especially for azopolymers.…”

Section: Discussionmentioning

confidence: 99%

Photoswitchable Adhesives Using Azobenzene‐Containing Materials

et al. 2020

Chemistry An Asian Journal

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Photoinduced reversible solid‐to‐liquid transitions of azobenzene‐containing materials can control adhesion. Photoswitchable adhesives based on azobenzene‐containing small molecules and polymers are under intense investigation. The melting points or glass transition temperatures of such azobenzene‐containing materials in trans and cis forms are above and below room temperature, respectively. Photoswitching of these materials results in reversible trans‐cis isomerization and solid‐to‐liquid transitions. The solid trans azobenzene‐containing materials have strong adhesion and the liquid cis azobenzene‐containing materials have weaker adhesion. In this Minireview, we introduce adhesives based on azobenzene‐containing small molecules and polymers. The remaining challenges and perspectives in the field of photoswitchable adhesives using azobenzene‐containing materials are also discussed.

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“…An overview of typical examples with adhesion strength over 1 MPa on diverse substrates is shown in Table 1. 23,53,[55][56][57][58][59][60][61][62] Typical molecular weights of these monomers are below 2,000 g/mol, with a minimum of 186 g/mol, whereas the binding strength values are comparable with those of commercial superglues, allowing SSSA to be worth investigated further as macroscopic adhesion materials.…”

Section: High-strength Supramolecular Adhesivesmentioning

confidence: 99%

Supramolecular adhesive materials from small‐molecule self‐assembly

et al. 2020

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Developing high-performance adhesive materials not only aims at industrial and social requirements but also bears the fundamental importance of understanding the chemical factors of biological adhesion to develop biomimetic adhesive materials. Owing to the wide development of supramolecular chemistry, numerous supramolecular tools are exploited and proved to be reliable in the replacement of traditional covalent materials by reversible noncovalent or dynamic covalent materials. Taking advantage of these readyto-use supramolecular toolboxes, supramolecular adhesive materials are rising and promising toward "smart" adhesives, that is, enabling responsiveness, reversibility, and recyclability. Compared with polymeric adhesive materials, low-molecular-weight adhesives feature chemically precise structure, easier engineering by molecular design, and hence higher reproducibility. However, it remains highly challenging to make high-performance adhesive materials by low-molecular-weight feedstocks. This review will focus on the recent advancement in the construction of supramolecular adhesive materials by smallmolecule self-assembly. The design guidelines and consideration on the molecular scale will be discussed and summarized on how to enhance the strength of adhesives. Meanwhile, owing to the dynamic nature of supramolecular self-assembly, several "smart" functions of such materials will be presented, such as stimuli-responsiveness and adaptiveness. Finally, current challenges and future perspectives of this emerging field will be proposed.

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Green-Light-Triggered Phase Transition of Azobenzene Derivatives toward Reversible Adhesives

Cited by 132 publications

References 32 publications

Increasing Photothermal Efficacy by Simultaneous Intra‐ and Intermolecular Fluorescence Quenching

Increasing Photothermal Efficacy by Simultaneous Intra‐ and Intermolecular Fluorescence Quenching

Photoswitchable Adhesives Using Azobenzene‐Containing Materials

Supramolecular adhesive materials from small‐molecule self‐assembly

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