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Visible-Light-Responsive Crystalline Solids by Equipping Covalent Organic Frameworks with donor-acceptor stenhouse adducts

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Chinese Journal of Chemistry 2023年第19期41卷 2469-2475页

作者： Yongli Duan Fanxi Sun Ang Gao Zhen Wang Xiaoyu Xiong Lijun Mao Bo Han Chao He Xu Deng Yonghao Zheng Dongsheng Wang School of Optoelectronic Science and Engineering University of Electronic Science and Technology of ChinaChengduSichuan610054 China State Key Laboratory of Southwestern Chinese Medicine Resources School of PharmacyChengdu University of Traditional Chinese MedicineChengduSichuan610041 China College of Polymer Science and Engineering Sichuan UniversityChengduSichuan610065 China Institute of Fundamental and Frontier Sciences University of Electronic Science and Technology of ChinaChengduSichuan610054 China Institute of Electronic and Information Engineering of UESTC in Guangdong DongguanGuangdong523808 China

Controlling properties of crystalline solids by light remains a challenge because the lack of intrinsic structural flexibility limits the necessary molecular mobility for photoisomerization. In this work, we reported a series of visible-light-responsive covalent organic frameworks (COFs) by introducing donor-acceptor stenhouse adducts (DASAs) with various electron-withdrawing moieties via a post-modified strategy. The DASAs-functionalized COFs exhibit distorted honeycomb layered topology with long-range periodicity. The DASAs grafted on the skeletons are pointing into the nanopores of COFs, which weakens intermolecular aggregation and ensures sufficient free volume to undergo reversible isomerization between linear and cyclic states. Furthermore, the crystalline and optical properties of COFs as well as the geometrical size and hydrophilicity inside the nanopores were reversibly controlled by alternating visible light irradiation and heat. Finally, methyl violet was used as the cargo molecules to be immobilized into the nanopores of COFs, which showed fast release under controlling of visible light.

关键词： Covalent organic frameworks donor-acceptor stenhouse adducts Photoresponsive Crystalline solids Cargo release lsomerization

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Learning from Spiropyrans:How to Make Further Developments of donor-acceptor stenhouse adducts

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Chinese Journal of Chemistry 2021年第4期39卷 985-998页

作者： Yongli Duan Haiquan Zhao Chaoyue Xiong Lijun Mao Dongsheng Wang Yonghao Zheng School of Optoelectronic Science and Engineering University of Electronic Science and Technology of ChinaJianshe North Road Section 2 No.4ChengduSichuan 610054China Institute of Electronic and Information Engineering of UESTC in Guangdong Zongbu Second Road No.17DongguanGuangdong523808 China

donor-acceptor stenhouse adducts(DASAs)as a species of novel photochromic molecules,have been developing rapidly and attracting broad researchers’sights since *** show visible/near-infrared(NIR)light induced linear-to-cyclic isomerization and heat induced cyclic-to-linear isomerization,therefore they are attractive in photoresponsive hydrogels,drug delivery,cell culturing and tissue *** a series of well-known photoresponsive molecules,spiropyrans(SPs)show similar molecular properties and comparable photoswitching with *** light triggers closed-to-open(also known as spirocyclic(SC)-to-merocyanine(MC))isomerization of SPs,while the reversed open-to-closed isomerization occurs under visible light or *** irradiation switches the molecular color,scale,geometry,and polarity of SPs and DASAs *** the researches on DASAs are still in the infancy,the chemical structures,isomerization mechanisms and potential applications need to be further investigated and *** well-studied SPs have important reference values to the comprehensive developments of *** the present review,we summarized,compared and discussed SPs and DASAs with regards to their molecular structures,synthesis,photoswitching and *** also make our perspective on the developments of DASA in future.

关键词： Photoresponsive donor-acceptor stenhouse adducts Spiropyrans Applications Isomerization

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

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Science China Chemistry 2024年第5期67卷 1636-1646页

作者： Jiaxing Zhang Qingyun Zhao Xinyan Su Afang Zhang Wen Li International Joint Laboratory of Biomimetic and Smart Polymers School of Materials Science and EngineeringShanghai UniversityShanghai 200444China

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.

关键词： dendrimers donor-acceptor stenhouse adducts isomerization confinement thermoresponsiveness

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