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Spiro-fused bicyclo[3,2,2]octatriene-cored triptycene:synthesis,molecular packing,and functional aggregates

Science China Chemistry 2021年第11期64卷 1976-1984页

作者： Qing Liu Xian Chen Zhibiao Zhou Tingting Huang Yanpei Wang Sheng Xie Zebing Zeng ben Zhong tang State Key Laboratory of Chemo/Biosensing and Chemometrics College of Chemistry and Chemical EngineeringHunan UniversityChangsha410082China Aggregation-Induced Emission(AIE)Institute Guangzhou Development DistrictHuangpuGuangzhou510530China Shenzhen Institute of Aggregate Science and Technology School of Science and EngineeringThe Chinese University of Hong KongShenzhen518172China

Aggregate science has led to the existence of functional properties at the aggregate level that significantly differs from those of corresponding single-molecule species,leading to a number of novel conceptual materials with state-dependent *** developing such materials,new molecular scaffolds that allow modulating the structural and functional properties of aggregates in a controlled manner could be extremely *** this study,we report a class of spiro-fused bicyclo[3,2,2]octatriene triptycene derivatives with a unique 3 D molecular scaffolding structure that displays aggregation-induced emission(AIE)activity with bright solid-state blue *** core scaffold features a Y-shaped bicyclo[3,2,2]octatriene backbone and a vertical crossover arrangement of adjacent spiro-conjugated *** classic bicyclo[2,2,2]octatrienes with high rigidity,this stereoscopic bicyclo[3,2,2]octatriene containing a seven-membered ring allows retaining certain flexibility in the molecular scaffold,which results in a weak fluorescence in dilute solutions(Φ_(F)<10%).However,the corresponding molecular aggregates emit intense fluorescence(Φ_(F)=50%-75%)and show prominent AIE activity because of the restriction of intramolecular scaffold ***,in principle,these stereoscopic scaffold constructions with partially restricted flexibility facilitate the assembly of multiple different crystalline packing structures in both porous and nonporous forms depending on the growth conditions of crystalline *** obtained crystals with regular voids(12.85×6.89Aeach)show reversible luminescence in response to the adsorption/desorption of iodine *** materials based on an unusual 3 D scaffold exhibit a high degree of structural modulation at the aggregate level and demonstrate potential applications in chemical sensing and flexible optoelectronics,which may open up the exploration of highly stereoscopic molecular building blocks for developing functi

关键词： aggregate science triptycene aggregation-induced emission organic porous material

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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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Multistimuli-Responsive Luminescent Porous Organic Polymers with Chiroptical Properties and Acid-Induced Degradation

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Chinese Journal of Chemistry 2024年第16期42卷 1886-1894页

作者： Youling He Dongyang Fan Liang Zhang Dong Wang Ting Han Rongrong Hu ben Zhong tang 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 Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and ReconstructionThe Hong Kong University of Science and TechnologyClear Water BayKowloonHong Kong999077China State Key Laboratory of Luminescent Materials and Devices Guangdong Provincial Key Laboratory of Luminescence from Molecular AggregatesSouth China Universityof TechnologyGuangzhouGuangdong 510640China School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhen(CUHK-Shenzhen)Guangdong 518172China

Porous organic polymers(POPs)have attracted great attention in past *** diverse functional POPs have been developed,multistimuli-responsive POPs with excellent aggregate-state luminescence together with good chiroptical properties have rarely been ***,two pairs of Salen-type enantiomeric PoPs with multistimuli-responsive luminescence and chiral features were designed and synthesized by facile polycondensation reactions between polyfunctional aggregation-induced emission luminogen(AlEgen)-containing salicylaldehyde derivatives and chiral *** Salen units in polymer backbones as tetradentate ligands,a series of POP-metal complexes were further *** obtained POPs and metal complexes show good porosity,high thermal stability,and obvious circular dichroism ***,benefiting from the coexistence of AlEgen and Salen units in polymer structures,these POPs exhibit excellent luminescence performance in aggregate states and tunable fluorescence behaviors in response to external stimuli of Zn^(2+)ion,mechanical forces,organic solvent,and *** to the dynamic feature of Schiff base C=N bonds,the present POPs can efficiently undergo hydrolysis reactions under strong acidic conditions to reproduce the AlEgencontaining monomers,and such an acid-induced degradation process can be directly visualized and dynamically monitored via fluorescence *** properties collectively make the POPs candidate materials for applications in heterogeneous asymmetric catalysis,fluorescence sensing,biomedicine,etc.

关键词： Polymers Stimuli-responsive luminescence Porous polymers Chirality Aggregation-induced emission Fluorescence Schiff bases Degradation

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1-((12-Bromododecyl)oxy)-4-((4-(4-pentylcyclohexyl)phenyl)ethynyl) benzene: Liquid crystal with aggregation-induced emission characteristics

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Science China Chemistry 2013年第9期56卷 1191-1196页

作者： CHEN YaFei LIN JieSheng YUAN WangZhang YU ZhenQiang LAM Jacky WingYip tang ben Zhong Shenzhen Key Laboratory of Functional Polymers School of Chemistry and Chemical EngineeringShenzhen University National Institutes for Food and Drug Control School of Chemistry and Chemical engineering Shanghai Jiao Tong University Department of Chemistry The Hong Kong University of Science & Technology

The luminescent liquid crystals (LLCs) are expected to solve the conflicts between the aggregation caused quenching and the requirement of aggregation or self-organization for LCs. Herein, we developed a new strategy of applying aggregation-induced emission (AIE) phenomenon to the molecular design of LCs towards LLCs. In this report, a calamitic liquid crystal based on tolane with AIE characteristics was successfully synthesized and the chemical structure was characterized by 1H, 13C NMR, and matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) high-resolution mass spectra. The fluorescence behavior was studied by fluorescence spectroscopy and the liquid crystal phase behaviors were investigated by differential scanning calorimetry (DSC), polarized optical microscopy (POM). The crystal structure was obtained by X-ray diffraction crystallography with P1 space group. Results demonstrated that the sample was AIE active and the LC phases sequence during cooling was nematic, smectic C and smectic B phase.

关键词： aggregation-induced emission tolane liquid crystal phase behavior

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Uncommon Intramolecular Charge Transfer Effect and Its Potential Application in OLED Emitters

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Chemical Research in Chinese Universities 2020年第1期36卷 61-67页

作者： WU Haozhong LUO Juanjuan XU Zeng WANG Zhiming MA Dongge QIN Anjun tang ben Zhong State Key Laboratory of Luminescent Materials and Devices Center for Aggregation-Induced EmissionKey Laboratory of Luminescence from Molecular Aggregates of Guangdong ProvinceGuangzhou International CampusSouth China University of Technology(SCUT)Guangzhou 510640P.R.China School of Petrochemical Engineering Shenyang University of Technology(SUT)Liaoyang 111003P.R.China Department of Chemistry The Hong Kong University of Science&Technology(HKUST)Clear Water BayKowloonHong KongP.R.China

Planarized intramolecular charge transfer(PLICT)state can facilitate the fluorescence process thanks to the relative excellent ***,we have discovered that the excited state quinone-conformation induced planarization(ESQIP)occurring on tetraphenylpyrazine(TPP)based derivatives could furnish them with PLICT *** to the well-known intramolecular charge transfer,strengthening the electron-donating nature on the donor(D)moiety did not impair the *** calculation results showed that planarization of the TPP based compounds scarcely accompanied with energy wastage while amount of energy was required for the torsion on *** the polar solvents,the energy consumption for planarization could further decrease,but that for twisting structure would *** take advantage of the transformation of the frontier orbitals'distribution,the PLICT type materials would perform a potential application on organic light-emitting diodes(OLEDs).

关键词： Planarized intramolecular charge transfer Tetraphenylpyrazine Excited state quinone-conformation induced planarization Organic light-emitting diode

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The specific detection of Cu(Ⅱ) using an AIE-active alanine ester

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Chinese Chemical Letters 2013年第8期24卷 668-672页

作者： Shuang Zhang Ji-Ming Yan An-Jun Qin Jing-Zhi Sun ben-Zhong tang MoE Key Laboratory of Macromolecule Synthesis and Functionalization Department of Polymer Science and EngineeringZhejiang University Department of Chemistry Institute of Molecular Functional Materialsthe Institute for Advanced Study(IAS)The Hong Kong University of Science & Technology

Cu（Ⅱ） detection is important because it plays crucial role in several biological processes and ecological *** techniques have attracted more and more attention in Cu（Ⅱ） *** this report,we contribute a novel strategy to use fluorescence spectroscopy for Cu（Ⅱ） specific *** specificity relies on the fact that,of the many metal cations,only Cu（Ⅱ） can catalyze the hydrolyzation of a-amino acid *** novelty originates from the unique aggregation-induced emission（AIE） property of the fluorescent *** designed a model a-amino acid ester（TPE-Ala） constructed with alanine and tetraphenylethene-functionalized methanol（TPE-methanol）.In comparison with the precursor TPE-Ala, TPE-methanol has lower solubility and is easy to form aggregates in water,thereby displaying a higher fluorescent ***,the Cu（Ⅱ） catalyzed hydrolyzation can be monitored by recording the fluorescence enhancement and fluorescent detection Cu（Ⅱ） is rationally achieved.

关键词： Aggregation-induced emission Fluorescence enhancement Cu(Ⅱ) catalyzed

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A Silole-Based Efficient Electroluminescent Material with Good Electron-Transporting Potential

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Chinese Journal of Chemistry 2015年第8期33卷 842-846页

作者： Changyun QuanI Han Nie Rongrong Hu Anjun Qin Zujin Zhao ben Zhong tang Guangdong Innovative Research Team State Key Laboratory of Luminescent Materials andDevices South China University of Technology Gt4angzhou 510640 China Department of Chemistry The Hong Kong University of Seience & Technology Clear Water Bay Kowloon Hong Kong China

A new silole derivative, 2,5-bis（7-（dimesitylboranyl）-9,9-dimethylfluoren-2-yl）- 1 -methyl- 1,3,4-triphenylsilole （（MesBF）2MTPS）, is synthesized and characterized. （MesBF）2MTPS shows a good fluorescence efficiency of 15% in THF solution and a higher efficiency of 86% in solid film, presenting an aggregation-enhanced emission charac- teristic. It is thermally and morphologically stable, with high decomposition and glass-transition temperatures of 257 and 171 ℃, respectively. The LUMO energy level （-2.96 eV） of （MesBF）zMTPS is lower than that of TPBi, revealing its electron-transporting potential. Efficient organic light-emitting diodes （OLEDs） are fabricated using （MesBF）2MTPS as emitter, which radiates yellow light at 554 nm, and affords high maximum luminance, current efficiency, and external quantum efficiency of 48348 cd·m^-2, 12.3 cd·A^-1, and 4.1%, respectively.

关键词： silole aggregation-enhanced emission electroluminescence electron transporter organic light-emitting diodes

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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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HYPERBRANCHED CONJUGATIVE MACROMOLECULES CONSTRUCTED FROM TRIPLE-BOND BUILDING BLOCKS

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Chinese Journal of Polymer Science 2005年第6期23卷 567-591页

作者： Matthias HaeuBler Hong-chen Dong Jacky Wing Yip Lam Rong-hua Zheng An-jun Qin ben-zhong tang Department of Chemistry The Hong Kong University of Science ＆ Technology Clear Water Bay Kowloon Hong Kong China Department of Polymer Science and Engineering Zhejiang University Hangzhou 310027 China

Polycyclotrimerization and polycoupling of acetylenic monomers respectively furnish hyperbranched polyarylenes and polyynes with high molecular weights （up to 1 × 10^6） in high yields （up to 99.9%）. The polymers possess low intrinsic viscosities and high thermal stabilities, losing little of their weights when heated to 〉 400℃. Upon pyrolysis at 〉 800℃, the polymers graphitize with high char yields （up to 86%）. Hyperbranched polyarylenes efficiently emit deep-blue to blue-green lights with fluorescence quantum yields up to 98% and strongly attenuate intense laser pulses with optical power-limiting performances superior to that of C60, a well-known optical limiter. Poly（alkenephenylenes）, poly（aroylarylenes） and polyynes are readily cross-linkable by UV irradiation, serving as excellent photoresist materials for the generation of patterns with nanometer resolution. Thin films of hyperbranched polyynes exhibit very high refractive indexes （n up to 1.86）. The internal and terminal acetylene moieties of the polyynes readily form complexes with cobalt carbonyls, which can be transformed into soft ferromagnetic ceramics with high magnetic susceptibilities （Ms up to ca. 118 emu/g） and near-zero magnetic losses.

关键词： Hyperbranched polymers Alkyne polycyclotrimerization Alkyne polycoupling Polyarylenes Polyynes Optical materials Photoresists Soft ferromagnetic ceramics

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Chromene-based Bio AIEgens:'in-water' synthesis,regiostructure-dependent fluorescence and ER-specific imaging

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National Science Review 2023年第11期10卷 118-127页

作者： Xu-Min Cai Yuting Lin Jianyu Zhang Ying Li Zhenguo tang Xuedan Zhang Ying Jia Wenjin Wang Shenlin Huang Parvej Alam Zheng Zhao ben Zhong tang Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources International Innovation Center for Forest Chemicals and MaterialsCollege of Chemical EngineeringNanjing Forestry University School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhen(CUHK-Shenzhen) Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and ReconstructionThe Hong Kong University of Science and Technology Clinical Translational Research Center of Aggregation-Induced Emission School of MedicineThe Second Affiliated HospitalSchool of Science and EngineeringThe Chinese University of Hong KongShenzhen(CUHK-Shenzhen)

Exploration of artificial aggregation-induced emission luminogens(AIEgens) has garnered extensive interest in the past two decades. In particular, AIEgens possessing natural characteristics(BioAIEgens) have received more attention recently due to the advantages of biocompatibility, sustainability and ***, the extremely limited number of BioAIEgens extracted from natural sources have retarded their development. Herein, a new class of Bio AIEgens based on the natural scaffold of chromene have been facilely synthesized via green reactions in a water system. These compounds show regiostructure-,polymorphism-and substituent-dependent fluorescence, which clearly illustrates the close relationship between the macroscopic properties and hierarchical structure of aggregates. Due to the superior biocompatibility of the natural scaffold, chromene-based BioAIEgens can specifically target the endoplasmic reticulum(ER) via the introduction of tosyl amide. This work has provided a new chromene scaffold for functional BioAIEgens on the basis of green and sustainable ’in-water’ synthesis, applicable regiostructure-dependent fluorescence, and effective ER-specific imaging.

关键词： chromene BioAIE ‘in-water’ chemistry regiostructure dependence ER-specific imaging

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