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aggregation-induced emission: a coming-of-age ceremony at the age of eighteen

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Science China Chemistry 2019年第9期62卷 1090-1098页

作者： Jie Yang Zhenguo Chi Weihong Zhu Ben Zhong Tang Zhen Li Tianjin Key Laboratory of Molecular Optoelectronic Sciences Department of Chemistry Institute of Molecular Aggregation Science Tianjin University Tianjin 300072 China PCFM Lab GD HPPC Lab Guangdong Engineering Technology Research Center for High-performance Organic and Polymer Photoelectric Functional Films State Key Laboratory of Optoelectronic Material and Technologies School of Chemistry and Chemical Engineering Sun Yat-sen University Guangzhou 510275 China Shanghai Key Laboratory of Functional Materials Chemistry Key Laboratory for Advanced Materials and Institute of Fine Chemicals East China University of Science and Technology Shanghai 200237 China Department of Chemistry The Hong Kong University of Science & Technology Hong Kong China Department of Chemistry Sauvage Center for Molecular Sciences Wuhan University Wuhan 430072 China

aggregation-induced emission(AIE) has drawn great attention worldwide for its unique optical phenomenon and huge potential applications. Since coined by Ben Zhong Tang et al. in 2001, AIE has been deeply investigated and widely utilized in many important areas, such as organic light-emitting diode(OLED), sensor, and bio-imaging. Herein, we highlight some important progress of AIE in these eighteen years, including the exploration of internal mechanism and potential applications. Furthermore,some other interestingly emissive behaviors, originating but distinguishing from the AIE concept, are presented. It is anticipated an overall understanding about AIE could be easily caught from this short review for scientists, no matter whether they are involved in this exciting and rising research area or not.

关键词： aggregation-induced emission internal mechanism potential application extension

A cyanostilbene-based molecule with aggregation-induced emission properties: amplified spontaneous emission, protonation effect and electroluminescence

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Science China Chemistry 2019年第2期62卷 212-219页

作者： Yujie Dong Suqian Ma Xiaoyu Zhang Jingyu Qian Nianyong Zhu Bin Xu Cheuk-Lam Ho Wenjing Tian Wai-Yeung Wong Institute of Molecular Functional Materials and Department of Chemistry Hong Kong Baptist University State Key Laboratory Breeding Base of Green Chemistry Synthesis Technology College of Chemical Engineering Zhejiang University of Technology State Key Laboratory of Supramolecular Structure and Materials Jilin University Department of Applied Biology & Chemical Technology The Hong Kong Polytechnic University

A terpyridine-substituted cyanostilbene derivative(Z)-2-(4′-([2,2′:6′,2″-terpyridin]-4′-yl)-[1,1′-biphenyl]-4-yl)-3-phenylacrylonitrile(CNSTPy) was synthesized and characterized. The compound exhibits remarkable aggregation-induced emission phenomenon and its single crystal shows a blue emission with fluorescent efficiency as high as 45%. Based on its aggregation state behavior, multiple applications towards exploring its lasing, fluorescence switching and electroluminescence properties were realized. Amplified spontaneous emission(ASE) was observed from the crystal and verified by the variable pump strip method, with a threshold value of ～1.5 m J cm^(-2). The protonation/deprotonation processes accompanied by the formation of different molecular aggregation structure result in the distinct blue and yellow emissions. Additionally, the molecule also shows a moderate electroluminescence performance.

关键词： aggregation-induced emission cyanostilbene amplified spontaneous emission protonation effect

aggregation-induced Emission-active Hyperbranched Poly (tetrahydropyrimidine)s Synthesized from Multicomponent Tandem Polymerization

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Chinese Journal of Polymer Science 2019年第4期37卷 428-436,I0008页

作者： Yuzhang Huang Ping Chen Bo Wei Rongrong Hu Ben Zhong Tang State Key Laboratory of Luminescent Materials and Devices Center for Aggregation-Induced EmissionSouth China University of Technology Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and ReconstructionThe Hong Kong University of Science & Technology

Hyperbranched polymer with highly branched three-dimensional topological structure, a large number of end groups, and multifaceted functionalities have gained much attention, while polymers with aggregation-induced emission(AIE) properties become a group of popular luminescent materials recently. The design and synthesis of AIE-active hyperbranched polymers, which combine the advantages of these two types of materials, are attractive but challenging. In this work, four hyperbranched poly(tetrahydropyrimidine)s were synthesized from the metal-free room temperature multicomponent tandem polymerization of diester group-activated internal alkyne,polyfunctional aromatic amines, and formaldehyde in methanol under the catalysis of acetic acid. Through different monomer combination and controlling the monomer loading order, hyperbranched polymers with various topological structures as well as sequences of different functional groups in the polymer backbone were obtained with high molecular weights(up to 3.0 × 10~4 g/mol) in high yields(up to 98%). The hyperbranched poly(tetrahydropyrimidine) emitted faintly in solution, while its luminescence was notably enhanced in the aggregated state, suggesting its typical aggregation-induced emission property. It is anticipated that the multicomponent polymerization may provide a synthetic platform for the construction of hyperbranched polyheterocycles with diverse structures and functionalities.

关键词： Hyperbranched polymer Multicomponent tandem polymerization aggregation-induced emission Polyheterocycle

Recent Progress in Fluorescent Vesicles with aggregation-induced Emission

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Chinese Journal of Polymer Science 2019年第4期37卷 352-371,I0006页

作者： Hui Chen Min-Hui Li Chimie ParisTech PSL University ParisCNRSInstitut de Recherche de Chimie Paris Beijing Advanced Innovation Center for Soft Matter Science and Engineering Beijing University of Chemical Technology

Fluorescent vesicles have recently attracted increasing attention because of their potential applications in bioimaging,diagnostics, and theranostics, for example, in vivo study of the delivery and the distribution of active substances. However, fluorescent vesicles containing conventional organic dyes often suffer from the problem of aggregation-caused quenching(ACQ) of fluorescence.Fluorescent vesicles working with aggregation-induced emission(AIE) offer an extraordinary tool to tackle the ACQ issue, showing advantages such as high emission efficiency, superior photophysical stability, low background interference, and high sensitivity. AIE fluorescent vesicles represent a new type of fluorescent and functional nanomaterials. In this review, we summarize the recent advances in the development of AIE fluorescent vesicles. The review is organized according to the chemical structures and architectures of the amphiphilic molecules that constitute the AIE vesicles, i.e., small-molecule amphiphiles, amphiphilic polymers, and amphiphilic supramolecules and supramacromolecules. The studies on the applications of these AIE vesicles as stimuli-responsive vesicles,fluorescence-guided drug release carriers, cell imaging tools, and fluorescent materials based on fluorescence resonance energy transfer(FRET) are also discussed.

关键词： Vesicles Polymersomes aggregation-induced emission Small-molecule amphiphiles Amphiphilic polymers Amphiphilic supramolecules Amphiphilic supramacromolecules

Stiff-stilbene derivatives as new bright fluorophores with aggregation-induced emission

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Science China Chemistry 2019年第9期62卷 1194-1197页

作者： Ya-Hang Wu Kun Huang Shu-Feng Chen Yu-Zhe Chen Chen-Ho Tung Li-Zhu Wu Key Laboratory of Photochemical Conversion and Optoelectronic Materials Technical Institute of Physics and Chemistry Chinese Academy of Sciences Beijing 100190 China University of the Chinese Academy of Sciences Beijing 100049 China College of Chemistry and Chemical Engineering Inner Mongolia University Hohhot 010021 China

Stiff-stilbene derivatives have been widely explored as molecular rotors, molecular force probes and optical switches with excellent performance. However, their function as fluorophores is poorly understood. In the present work, we design three stiffstilbene derivatives and study their photophysical properties. These compounds exhibit very weak emission in solution but significantly enhanced monomer emission in viscous solvent, bright excimer emission in aggregates and at solid state. Detailed spectroscopic studies, single crystal structural analysis, powder X-ray diffraction(XRD) as well as effects of substituents have been carefully examined. They provide direct evidence that intermolecular interactions and molecular packing, which can restrict bond vibration and rotation, are responsible for the bright aggregation-induced emission.

关键词： stiff-stilbene derivatives intermolecular interactions molecular packing aggregation-induced emission

aggregation-induced emission luminogen for specific identification of malignant tumour in vivo

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Science China Chemistry 2020年第3期63卷 393-397页

作者： Jianlei Shen Kun Tao Peilin Gu Chen Gui Dong Wang Zhenyu Tan Lihua Wang Zhiming Wang Anjun Qin Ben Zhong Tang Shisan Bao School of Chemistry and Chemical Engineering Shanghai Jiao Tong UniversityShanghai 200240China Tongren Hospital School of MedicineShanghai Jiao Tong UniversityShanghai 200240China Discipline of Pathology Bosch Institute and School of Medical SciencesCharles Perkins CentreThe University of SydneyAustralia Division of Physical Biology CAS Key Laboratory of Interfacial Physics and TechnologyShanghai Synchrotron Radiation FacilityShanghai Institute of Applied PhysicsChinese Academy of SciencesShanghai 201800China Department of Chemistry HKUST Jockey Club Institute for Advanced StudyInstitute of Molecular Functional MaterialsDivision of Biomedical EngineeringState Key Laboratory of Molecular NeuroscienceDivision of Life ScienceThe Hong Kong University of Science and TechnologyHong KongChina State Key Laboratory of Luminescent Materials and Devices South China University of TechnologyGuangzhou 510640China

Colorectal cancer(CRC)is still a major killer,mainly due to the lack of early detection biomarker with sensitivity/specificity.Conventional histopathology is the gold standard approach in practice,but there are still some issues(false diagnosis and long waiting period).aggregation-induced emission(AIE)is a novel photophysical phenomenon which has been widely utilized for biological imaging in vitro,including malignant cells,showing remarkable imaging contrast and enhanced emission in high concentrated state.However,it is unclear if AIE dyes can identify malignant cells specifically in vivo.A great challenge for specific labeling of malignant cells is probably ascribed to the complex compositions in tumor tissues.Herein,an AIE dye-based mitochondria-targeted histological staining strategy was employed to localize cancer and the metastatic track in the fresh colorectal cancer.This novel approach holds great potential to revolutionize the clinical diagnosis and intervention for devastating malignancy.

关键词： aggregation-induced emission histological staining colorectal cancer

Conformational sensitivity of tetraphenyl-1,3-butadiene derivatives with aggregation-induced emission characteristics

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Science China Chemistry 2019年第10期62卷 1393-1397页

作者： Yahui Zhang Huanyu Xu Weiquan Xu Chen Zhang Jianbing Shi Bin Tong Zhengxu Cai Yuping Dong Beijing Key Laboratory of Construction Tailorable Advanced Functional Materials and Green Applications School of Materials Science and EngineeringBeijing Institute of Technology

Organic dyes with conformational sensitivity can be used to probe weak interactions at the molecular level.Here,three molecules based on tetraphenyl-1,3-butadienes(TPBs)were synthesized and studied with respect to their synthesis,structural characterization and potential application.All TPBs showed aggregation-induced emission(AIE)characteristics and sensitive conformational properties,in which the emission wavelengths could be changed in different states.The TPBs single crystals revealed that the phenyl groups at the 4-position of the 1,3-butadienes contributed to their conformational sensitivity.Furthermore,the potential application for monitoring the interactions among polyelectrolyte complexes and metal ions was explored,and the results showed that TPBs could be used for sensitively probing some weak interactions by changing the emission wavelengths due to their conformation-sensitive properties.TPBs may become a new star in AIE research fields.

关键词： tetraphenyl-1 3-butadienes(TPBs) aggregation-induced emission(AIE) polyelectrolyte complexes(PEC) conformational sensitivity

Detection of the critical micelle concentration of cationic and anionic surfactants based on aggregation-induced emission property of hexaphenylsilole derivatives

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Science China Chemistry 2009年第6期52卷 755-759页

作者： TANG Li JIN JiaKe ZHANG Shuang MAO Yu SUN JingZhi YUAN WangZhang ZHAO Hui XU HaiPeng QIN AnJun TANG Ben Zhong Department of Polymer Science and Engineering Institute of Biomedical MacromoleculesZhejiang UniversityHangzhou 310027China Department of Chemistry The Hong Kong University of Science&TechnologyHong KongChina

We report a fluorescence "turn-on" method to detect the critical micelle concentration (CMC) of surfactants. This method works well for both cationic and anionic surfactants. It employs an unprecedented mechanism (aggregation-induced emission, or AIE) to determine the CMC values, and the results are consistent with the data obtained by the classical techniques. In addition, this method renders the convenient detection of the CMC values. Any large and professional instruments are unnecessary, instead, a portable UV lamp and an ultrasonic generator are enough to carry out the detection in an ordinary laboratory. Considering that micelles are interesting entities and have found applications in many important fields such as emulsion polymerization, template of nanosized materials synthesis, controllable drug delivery and macromolecular self-assembling. Our experimental results may offer a facile, sensitive and promising method to detect the formation of micelles constructed by the new amphiphilic molecules and macromolecules.

关键词： aggregation-induced emission critical micelle concentration fluorescence probe

Unsymmetrical photochromic bithienylethene-bridge tetraphenylethene molecular switches:Synthesis,aggregation-induced emission and information storage

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Chinese Chemical Letters 2020年第2期31卷 361-364页

作者： Liangwei Ma Chengpeng Li Qing Yan Sheng Wang Wangen Miao Derong Cao School of Chemistry and Chemical Engineering Key Lab of Clean Energy Materials Chemistry of Guangdong Higher Education InstitutesLingnan Normal UniversityZhanjiang 524048China School of Chemistry and Chemical Engineering State Key Laboratory of Luminescent Materials and DevicesSouth China University of TechnologyGuangzhou 510641China

aggregation-induced emission(AIE) active photochromic molecules have attracted growing attention for their versatile applications.Here we designed and synthesized five newly unsymmetrical photochromic diarylethene(DAE) dyads(BTE1-5) by connecting tetraphenylethene(TPE) and aromatic substituent via bithienylethene(BTE) bridge.The chemical structures of those compounds were identified by ^1H NMR,^(13)C NMR and HRMS.The absorption and emission of these dyads were investigated by UV-vis and fluore scence spectroscopy,respectively.The results showed that all those compounds exhibited typically AIE or aggregation-induced emission enhancement(AIEE) characteristic.Particularly,when an aggregationcaused quenching(ACQ) fluorophore(triphenylamine) was grafted to the molecule,connecting with TPE via BTE-bridge,the ACQ phenomenon was dissipated and converted to an AIE luminophore,and those compounds exhibited photochromism upon irradiation with alternative UV and visible light.The solution or solid of those compounds showed distinctly fluorescence switching "ON" or "OFF" observation upon irradiation with alternative UV and visible light.It is interesting that BTE1 could be applied in recording and rewritable information storage,and the cyclization quantum yields could be affected by substituent significantly.

关键词： aggregation-induced emission Bithienylethene Photochromic Tetraphenylethene Information storage