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Oxygen and sulfur-based pure n-electron dendrimeric systems:generation-dependent clusteroluminescence towards multicolor cell imaging and molecular ruler

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Science China Chemistry 2021年第11期64卷 1990-1998页

作者： Zhijun zhang haoke zhang Miaomiao Kang Na Li Dong Wang Ben Zhong Tang Center for AIE Research Shenzhen Key Laboratory of Polymer Science and TechnologyGuangdong Research Center for Interfacial Engineering of Functional MaterialsCollege of Material Science and EngineeringShenzhen UniversityShenzhen518060China Key Laboratory of Macromolecular Synthesis and Functionalization(Ministry of Education) Department of Polymer Science and EngineeringZhejiang UniversityHangzhou310027China Shenzhen Institute of Molecular Aggregate Science and Engineering School of Science and EngineeringThe Chinese University of Hong KongShenzhen518172China

Dendrimers,as the latest generation of artificial macromolecules,have aroused great attention in the field of clusteroluminescence owing to their unique structural and photophysical ***,previously reported dendrimers with clusteroluminescenence property usually containπelectrons-involved carbonyl groups and/or environment-sensitive aliphatic amine moieties in their structures,thus complicating the interpretation of the emission *** the other hand,a systematic investigation on the luminescence performance of dendrimers with diverse generations is significantly important for the researchers to gain further mechanistic insights into the clusteroluminescence,but has still been scarcely *** this contribution,we reported a series of oxygen and sulfur-based pure n-electron dendrimers with different generations from G1 to *** from the highly-branched three-dimensional crowded molecular structures,all these dendrimers exhibited bright fluorescence emission in visible light region due to their prominent clusteroluminescence ***,the fluorescence intensity and emission wavelength were simultaneously boosted as their generation increased due to the more crowded molecular architectures,as well as the formation of tighter and larger clusters at higher ***,these dendrimers also showed concentration-and aggregation-enhanced luminescence behaviors,presenting typical aggregation-induced emission(AIE)*** with remarkable water solubility and biocompatibility as well as the excellent photostability,the G3 dendrimer selected as a representative was successfully applied in the multicolor cell *** addition,the G3 dendrimer was also proved to be capable of acting as a molecular ruler to detect specific-sized molecule in aqueous *** work not only validated the rationality of the clusteroluminescence mechanism but also offered high-performance clusteroluminogens for practical application.

关键词： clusteroluminescence aggregation-induced emission dendrimer cell imaging molecular ruler

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Restriction of Intramolecular Motion(RIM):Investigating AIE Mechanism from Experimental and Theoretical Studies

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Chemical Research in Chinese Universities 2021年第1期37卷 1-15页

作者： zhang Jianyu zhang haoke LAM Jacky W.Y. TANG Ben Zhong Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration and ReconstructionInstitute for Advanced Studyand Department of Chemical and Biological EngineeringThe Hong Kong University of Science&TechnologyClear Water BayKowloonHong KongP.R.China MOE Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and EngineeringZhejiang UniversityHangzhou310027P.R.China Center for Aggregation-Induced Emission SCUT-HKUST Joint Research InstituteState Key Laboratory of Luminescent Materials and DevicesSouth China University of TechnologyGuangzhou510640P.R.China Guangzhou Development District AIE InstituteGuangzhou510530P.R.China

Mechanistic studies promote scientific development from phenomena to ***-induced emission(AIE),as an unusual photophysical phenomenon,builds the bridge between molecular science and aggregate *** the twenty-year development of AIE,restriction of intramolecular motion(RIM)has been verified as the working mechanism of AIE *** this review,these mechanistic works about RIM are summarized from experimental and theoretical ***,the experimental studies are introduced from three parts:external rigidification,structural modification and structural *** the theoretical part,calculations on the low-frequency motion of AIEgens have been performed to prove the RIM *** virtue of the theoretical calculations,some new mechanisms are proposed to supplement the RIM,such as restriction of access to conical intersection,suppression of Kasha transition,restriction of access to dark state,*** is foreseeable that the RIM mechanism will unify the photophysical theories for both molecules and aggregates,and inspire more progress in aggregate science.

关键词： Aggregation-induced emission(AIE) Restriction of intramolecular motion Photophysical mechanism Aggregate science

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Emerging Clusteroluminescence from Complexes between Carbonyl-Based Polymers and Organic Base

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Chinese Journal of Chemistry 2023年第22期41卷 3012-3018页

作者： Hongwei Lu Yuan Xie Ziteng zhang Zhiming zhang Jing ZhiSun haoke zhang Ben Zhong Tang MOE Key Laboratory of Macromolecular Synthesis and Function alization Department of Polymer Science and EngineeringZhejiang UniversityHangzhouZhejiang 310058China Zhejiang-srael Joint Laboratory of Self-Assembling Functional Materials ZJU-Hangzhou Global Scientific and Technological Innovation CenterZhejiangUniversityHangzhouZhejiang311215China Centreof HealthcareMaterials ShaoxingInstituteZhejiangUniversityShaoxingZhejiang312000China Centerfor AlE Research College of Materials Science and EngineeringShenzhen UniversityShenzhenGuangdong 518061China School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhen(CUHK-Shenzhen)ShenzhenGuangdong518172China

The study of luminescence phenomena in non-conjugated systems,namely clusteroluminescence,has gained significant attention for the development of advanced luminescent *** conventional strategies to manipulate the luminescent performances are based on complicated chemical *** contrast,nature employs complexation to modulate luminescence,inspiring researchers to adopt an engineering approach for the construction of efficient *** this work,we explore the complexationinduced clusteroluminescence of carbonyl-based polymers with nitrogen-containing organic bases,exemplified by polyamide,polyester,polycarbonate,and poly(monothiocarbonate).

关键词： Clusteroluminescence Carbonyl-based polymers Through-space interactions Fluorescence Functional polymers

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Aggregation-Induced Emission:A Rising Star in Chemistry and Materials Science

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Chinese Journal of Chemistry 2021年第3期39卷 677-689页

作者： Ting Han Dingyuan Yan Qian Wu Nan Song haoke zhang Dong Wang Center for AIE Research Shenzhen Key Laboratory of Polymer Science and TechnologyGuangdong Research Center for Interfacial Engineering of Functional MaterialsCollege of Materials Science and EngineeringShenzhen UniversityShenzhenGuangdong 518060China College of Physics and Optoelectronic Engineering Shenzhen UniversityShenzhenGuangdong 518060China Department of Chemistry The Hong Kong University of Science and TechnologyClear Water BayKowloonHong KongChina

Aggregation-induced emission(AIE)refers to a photophysical effect that the luminescence of aggregates is stronger than that of the dispersed *** the concept of AIE was coined by Professor Ben Zhong Tang and co-workers in 2001,AIE has evolved from a simple luminescent phenomenon to a multidisciplinary research field with a widespread *** has changed people's way of thinking about chromophore aggregation and greatly promoted the development of advanced luminescent *** the 20-year development,diverse AIE luminogens(AlEgens)with attractive functionalities have been developed and remarkable achievements have been made in the mechanistic study and high-tech applications of *** this review,we provide an overview of the historical development and representative achievements of AIE *** on the application of AIE in aggregate science are also briefly discussed to guide the future development in this field.

关键词： Aggregation-induced emission Fluorescence Materials science Structures Mechanisms

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The superiority of nonconjugated structures in fluorescence:through-space ***-bond charge transfer

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Science China Chemistry 2024年第9期67卷 3121-3130页

作者： Weihao Tu Zuping Xiong Lei Wang Jianyu zhang Jing Zhi Sun haoke zhang Ben Zhong Tang MOE Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and EngineeringZhejiang UniversityHangzhou 310058China Zhejiang-Israel Joint Laboratory of Self-Assembling Functional Materials ZJU-Hangzhou Global Scientific and Technological Innovation CenterZhejiang UniversityHangzhou 311215China Centre of Healthcare Materials Shaoxing InstituteZhejiang UniversityShaoxing 312000China Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and ReconstructionThe Hong Kong University of Science and TechnologyHong Kong 999077China School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhen(CUHK-Shenzhen)Guangzhou 518172China

Constructing charge transfer(CT)state by introducing donor(D)and acceptor(A)is an efficient strategy to regulate the photophysical properties of luminescent *** CT-type luminophores are built onπ-conjugated fused-ring structures,which always show hybrid CT/locally excited(LE)states and luminescence quenching effect in the aggregate *** this work,eight conjugated biphenyl(BP)and nonconjugated diphenylmethane(DPM)derivatives with different donors and acceptors are synthesized to investigate the CT *** photophysical characterization and theoretical calculation demonstrate that the through-space CT(TSCT)in nonconjugated DA-DPM exhibit superior photophysical performance than the conjugated DA-BP with through-bond CT(TBCT),the main manifestations are as follows:(1)TSCT luminophores produce longer maximum emission wavelength(λ_(em))than the corresponding TBCT *** example,the longest λ_(em)of DMA-CN-DPM(DMA,dimethylamino)is 621 nm but the corresponding λ_(em)of DMA-CN-BP is only 480 nm.(2)TSCT-based DA-DPM demonstrates more sensitive responsiveness to environmental stimuli such as temperature and polarity.(3)Complete separation of the the highest occupied molecular orbital(HOMO)and the lowest unoccupied molecular orbital(LUMO)distribution exists in all kinds of conformation of DA-DPM,which was hard to realize in conjugated DA-BP.

关键词： through-space charge transfer through-space conjugation clusteroluminescence diphenylmethane

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Theranostic hyaluronic acid prodrug micelles with aggregation- induced emission characteristics for targeted drug delivery

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Science China Chemistry 2016年第12期59卷 1609-1615页

作者： Lin Wang haoke zhang Anjun Qin Qiao Jin Ben Zhong Tang Jian Ji Key Laboratory of Macromolecular Synthesis and Functionalization Ministry of Education Department of Polymer Science and Engineering Zhejiang University Hangzhou 310027 China State Key Laboratory of Luminescent Materials and Devices South China University of Technology Guangzhou 510640 China Department of Chemistry The Hong Kong University of Science ＆ Technology Kowloon Hong Kong China

Theranostic hyaluronic acid(HA) prodrug micelles with pH-responsive drug release and aggregation-induced emission(AIE)properties were prepared by chemical graft of biomimetic phosphorylcholine(PC), anticancer drug doxorubicin(DOX) and AIE fluorogen tetraphenylene(TPE) to the HA backbone. DOX was conjugated to the HA backbone by a hydrazone bond which can be hydrolyzed under acidic environment and result in pH-triggered smart release of DOX. The TPE units with typical AIE characteristics were applied for real time drug tracking in cancer cells. The HA-based prodrugs could self-assemble into micelles in aqueous solution as confirmed by the dynamic light scattering(DLS) and transmission electron microscopy(TEM). The intracellular distribution of HA prodrug micelles could be clearly observed by fluorescence microscopy based on the strong fluorescence of TPE. Moreover, after treated with the micelles, stronger fluorescence of TPE in CD44 overexpressed MDA-MB-231 cancer cells was observed, compared to the CD44 negative cell line, NIH3T3 cells, suggesting efficient cell uptake of HA prodrug micelles by receptor-mediated endocytosis. The cell viability results indicated that the prodrug micelles could inhibit the proliferation of the cancer cells effectively. Such pH-triggered theranostic drug delivery system with AIE features can provide a new platform for targeted and image-guided cancer therapy.

关键词： hyaluronic acid AIE prodrug drug delivery

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Themed Issue on Aggregation-induced Emission

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Chemical Research in Chinese Universities 2021年第1期37卷 I0001-I0002页

作者： zhang haoke TANG Ben Zhong Zhejiang University| Hong Kong University of Science and Technology&South China University of Technology

Twenty years of aggregation-induced emission(AIE)research has witnessed the flourishing development of aggregate-related disciplines(ie,solid-state emitters).From photophysical mechanisms to structural frameworks and thence to functional applications,AIE systems possess many unique and superior characteristics compared to the traditional structures with detrimental aggregation-caused quenching(ACQ)effct.

关键词： aggregation aggregate quenching

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Clusteroluminescence:A gauge of molecular interaction

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Chinese Chemical Letters 2023年第5期34卷 165-173页

作者： Bin Liu Bo Chu Lixun Zhu haoke zhang Wang-zhang Yuan Zheng Zhao Wen-Ming Wan Xing-Hong zhang School of Energy and Power Engineering North University of ChinaTaiyuan 030051China MOE Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and EngineeringZhejiang UniversityHangzhou 310027China School of Chemistry and Chemical Engineering Frontiers Science Center for Transformative MoleculesShanghai Key Lab of Electrical Insulation and Thermal AgingShanghai Electrochemical Energy Devices Research CenterShanghai Jiao Tong UniversityShanghai 200240China School of Science and Engineering The Chinese University of Hong KongShenzhen 518172China State Key Laboratory of Structural Chemistry Key Laboratory of Coal to Ethylene Glycol and Its Related TechnologyCenter for Excellence in Molecular SynthesisFujian Institute of Research on the Structure of MatterChinese Academy of SciencesFuzhou 350002China

Clusteroluminescence(CL)materials,as an emerging class of luminescent materials with unique photophysical properties,have received increasing attention owing to their great theoretical significance and potential for biological *** much progress has been made in the design,synthesis and application of CL materials,there is still a big challenge in the emission *** far,throughspace interaction has been proposed as the preliminary mechanism of the corresponding clusterizationtriggered emission(CTE)effect,but a systematic theory is still *** review summarizes the current mechanistic understanding of CL materials including organic/inorganic small molecules,and polymers with/without isolated aromatic *** addition,some strategies to achieve high quantum yield,adjustable emission color,and persistent room temperature phosphorescence in CL materials are also *** last,a perspective of the mechanism and application of CL materials are demonstrated,which inspire the researchers working on the development of new kinds of functional materials.

关键词： Clusteroluminescence Clusterization-triggered emission Through-space interaction Non-conjugated structure

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Manipulation of clusteroluminescence in carbonyl-based aliphatic polymers

Aggregate

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Aggregate 2022年第6期3卷 166-174页

作者： Ziteng zhang Zuping Xiong Bo Chu Zhiming zhang Yuan Xie Lei Wang Jing Zhi Sun haoke zhang Xing-Hong zhang Ben Zhong Tang MOE Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and EngineeringZhejiang UniversityHangzhouChina ZJU-Hangzhou Global Scientific and Technological Innovation Center HangzhouChina Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates South China University of TechnologyGuangzhouChina School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhenChina Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction and Institute for Advanced Study The Hong Kong University of Science and TechnologyHong Kong SARChina Center for AIE Research College of Materials Science and EngineeringShenzhen UniversityShenzhenChina

Clusteroluminogens(CLgens),nonconjugated structures with visible luminescence at the clustering state,have recently received remarkable attention due to their great theoretical significance and practical *** carbonyl-based aliphatic polymers,(n,π*)transition of carbonyl groups and the through-space interactions have been demonstrated to play an important role in their clusteroluminescence(CL)properties,but it is still a big challenge to manipulate their CL at the molecular *** this work,six nonconjugated carbonyl-based polymers with different heteroatoms and steric hindrances were synthesized,and their photophysical properties were systematically *** polymers all showed CL but with different emission efficiency and *** and theoretical studies indicated that the CL properties could be manipulated by changing the electronic structures of carbonyl groups and the rigidity of polymer *** work not only gains further insights into the CL mechanism but also provides reliable strategies to design and manipulate non-conjugated luminescent materials.

关键词： clusteroluminescence through-space interactions (n,π*)transition

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Manipulating noncovalent conformational lock via side-chain engineering for luminescence at aggregate level

Aggregate

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Aggregate 2024年第4期5卷 349-359页

作者： Mingbing Lian Yingxiao Mu Zecong Ye Ziying Lu Jingping Xiao Jianyu zhang Shaomin Ji haoke zhang Yanping Huo Ben Zhong Tang School of Chemical Engineering and Light Industry Analytical and Testing CenterGuangdong University of TechnologyGuangzhouChina Stratingh Institute for Chemistry and Zernike Institute for Advanced Materials University of GroningenGroningenThe Netherlands MOE Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and EngineeringZhejiang UniversityHangzhouChina School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongGuangdongChina

The unfavorable photochemical processes at the molecular level have become a bar-rier limiting the use of aromatic amides as high-performance luminescent ***,we propose a reliable strategy for manipulating noncovalent conformational lock(NCL)via side-chain engineering to burst out eye-catching luminescence at the aggregate *** to the invisible emission in dilute solutions,dyad OO with a three-centered H-bond gave the wondrous crystallization-induced emis-sion with a quantum yield of 66.8%and clusterization-triggered emission,which were much brighter than those of *** calculations demonstrate that crystallization-induced planarized intramolecular charge transfer(PICT),con-formation rigidiﬁcation,and through-space conjugation(TSC)are responsible for aggregate-state *** NCL composed of intramolecular N-H⋅⋅⋅Ointeractions could boost molecular rigidity and planarity,thus greatly facilitating PICT and *** study would inspire researchers to design efﬁcient luminescent materials at the aggregate level via rational conformational control.

关键词： aromatic amide clusterization-triggered emission crystallization-induced emission noncovalent confor-mational lock side-chain engineering

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