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Activated Internal Alkyne-Based Polymerization

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Chinese Journal of Chemistry 2022年第16期40卷 2001-2013页

作者： Baixue Li Jia Wang benzhao he Anjun Qin Ben Zhong Tang State Key Laboratory of Luminescent Materials and Devices Guangdong Provincial Key Laboratory of Luminescence from Molecular AggregatesCenter for Aggregation Induced EmissionAIE InstituteSouth China University of TechnologyGuangzhouGuangdong510640 China School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhenGuangdong518172 China Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction The Hong Kong University of Science and TechnologyClear Water BayKowloonHong KongChina Center for Advanced Materials Research Advanced Institute of Natural SciencesBejing Normal University at ZhuhaiZhuhaiGuangdong 519085China

As an emerging and efficient polymerization methodology,activated internal alkyne-based polymerization has been considered as a powerful tool for the construction of polymers with diverse architectures and versatile *** review focuses on the recent progresses in the polymerization using mono-activated,di-activated,in-situ generated,ring-strained ethynyl groups as substrates,coupling with post-modification on premade polymers containing activated internal ethynyl *** examples are used to illustrate the fundamental design strategy,the development of polymerization and post-functionalization,along with the properties and potential applications of the prepared ***,the challenges and perspectives in terms of new-type active alkynes,green polymerization methodology,tailored regio-/stereoselectivity modulation,and potentially expanded application in this area are also discussed.

关键词： Alkynes Polymerization Polymers Post-functionalization Property and application

Metal-free multicomponent polymerization of activated diyne,electrophilic styrene and isocyanide towards highly substituted and functional poly(cyclopentadiene)

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Science China Chemistry 2023年第3期66卷 863-869页

作者： Xinyue Liu Xueqin Yang Xin Li Jianwei Sun benzhao he Jacky W.Y.Lam Ben Zhong Tang Department of Chemistry and Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction Guangdong-Hong Kong-Macao Joint Laboratory of Optoelectronic and Magnetic Functional MaterialsThe Hong Kong University of Science and TechnologyHong Kong 999077China Center for Advanced Materials Research Beijing Normal University at ZhuhaiZhuhai 519085China School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhen 518172China Center for Aggregation-Induced Emission South China University of TechnologyGuangzhou 510640China

The development of a facile and efficient polymerization to prepare cyclopentadiene-containing polymers is of vital importance and highly desired. In this work, a metal-free multicomponent polymerization of activated diyne, electrophilic styrene and isocyanide for the preparation of highly substituted poly(cyclopentadiene) was established. Soluble and thermally stable polymers with high molecular weights are obtained in high yields under mild conditions. By introducing the tetraphenylethene or triphenylamine moiety into polymer backbones, the resultant polymers show unique aggregation-induced emission(AIE)characteristics. Interestingly, AIE polymers can also be generated in situ from non-AIE monomers. Moreover, the prepared polymers can generate photopatterns to function as photoresists and can also serve as visualizing agents to selectively stain the lipid droplets in live cells. This efficient polymerization will open up enormous opportunities for preparing functional cyclopentadiene-containing polymers applicable in diverse areas.

关键词： multicomponent polymerization activated alkynes highly substituted poly(cyclopentadiene)

Lab-in-cell based on spontaneous amino-yne click polymerization

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Science China Chemistry 2019年第9期62卷 1198-1203页

作者： Rong Hu Xu Chen Taotao Zhou Han Si benzhao he Ryan T. K. Kwok Anjun Qin Ben Zhong Tang State Key Laboratory of Luminescent Materials and Devices Center for Aggregation-Induced Emission South China University of Technology Guangzhou 510640 China Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration and Reconstruction Institute for Advanced Study Department of Chemical and Biological Engineering The Hong Kong University of Science & Technology Hong Kong China

Unnatural reaction in the living cells is a powerful tool for biological research. However, the polymerization inside cells is rarely reported. In this work, a lab-in-cell is illustrated based on our developed spontaneous amino-yne click polymerization. Carbonyl group activated terminal diyne can spontaneously polymerize with tetraphenylethene(TPE)-containing primary diamine inside cells, and polymer with weight-average molecular weight of 7,300 was yielded. By utilizing this in vivo amino-yne click polymerization and taking advantage of the aggregation-induced emission feature of TPE, a "turn-on" cell imaging was realized,and in-situ killing of cells was also acquired by destroying the structures of actin and tubulin, which cannot be realized by preprepared polymer. This strategy provides a useful platform and holds great promise in biochemistry and therapy applications.

关键词： lab in cell intracellular polymerization aggregation-induced emission cell imaging

In-situ generation of poly(quinolizine)s via catalyst-free polyannulations of activated diyne and pyridines

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Science China Chemistry 2022年第4期65卷 789-795页

作者： benzhao he Jiachang Huang Jing Zhang Xinyue Liu Dong Wang herman H.Y.Sung Yajun Liu Anjun Qin Jacky W.Y.Lam Ben Zhong Tang Center for Advanced Materials Research Science and Technology Experimental PlatformAdvanced Institute of Natural SciencesBeijing Normal University at ZhuhaiZhuhai 519085China Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstructionand Guangdong-Hong Kong-Macao Joint Laboratory of Optoelectronic and Magnetic Functional MaterialsThe Hong Kong University of Science&TechnologyKowloonHong KongChina Center for AIE Research College of Materials Science and EngineeringShenzhen UniversityShenzhen 518060China Department of Laboratory Medicine Nanfang HospitalSouthern Medical UniversityGuangzhou 510515China State Key Laboratory of Luminescent Materials and Devices Guangdong Provincial Key Laboratory of Luminescence from Molecular AggregatesCenter for Aggregation-Induced EmissionSouth China University of TechnologyGuangzhou 510640China HKUST-Shenzhen Research Institute Shenzhen 518057China Shenzhen Institute of Aggregate Science and Technology School of Science and EngineeringThe Chinese University of Hong KongShenzhen 518172China

The development of new polymerization routes to afford N-heterocyclic polymers is of vital importance and highly desired for various practical applications. herein, a facile and efficient polyannulation reaction of dual-activated alkyne and pyridines was developed to construct novel N-heterocyclic poly(quinolizine)s. This polymerization can proceed smoothly under catalystfree conditions with 100% atom utilization to furnish poly(quinolizine)s with high molecular weights(up to 34,100) and welldefined structures in acceptable yields. The resulting polymers show good solubility, high thermal stability and strong red emission. Moreover, the prepared poly(quinolizine)s exhibit low cytotoxicity and can selectively label lysosomes in live *** the remarkable advantages of readily available raw materials, mild polymerization conditions, atom economy, and excellent product performance, this new and efficient polymerization tool will open up enormous opportunities for preparing functional N-heterocyclic polymers.

关键词： polyannulation activated alkyne N-heterocyclic polymers poly(quinolizine)s bioimaging

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“On Water”Effect for Green Click Reaction:Spontaneous Polymerization of Activated Alkyne with“Inert”Aromatic Amine in Aqueous Media

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CCS Chemistry 2023年第2期5卷 385-396页

作者： Xinyue Liu Chen Zhang Lianrui Hu Jinghan Wang Kai Li Hai-Tao Feng Jacky WYLam benzhao he Ben Zhong Tang Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and ReconstructionGuangdong-Hong Kong-Macao Joint Laboratory of Optoelectronic and Magnetic Functional MaterialsThe Hong Kong University of Science and TechnologyClear Water BayKowloonHong Kong 999077 HKUST-Shenzhen Research Institute Shenzhen 518057 Department of Biomedical Engineering SUSTech Academy for Advanced Interdisciplinary StudiesSouthern University of Science and TechnologyShenzhen 518055 AIE Research Center Shaanxi Key Laboratory of PhytochemistryCollege of Chemistry and Chemical EngineeringBaoji University of Arts and SciencesBaoji 721013 Center for Advanced Materials Research Beijing Normal University at ZhuhaiZhuhai 519085 School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhen 518172

Organic reactions in water have attracted great attention due to their advantages such as unique reaction performance and environmental *** reactions as well as polymerizations in aqueous media have been extensively investigated,and so far,there has been a massive amount of reporting about polymerizations in ***,reports about click polymerization in water have been ***,click polymerization of activated alkyne and aromatic amine in aqueous media is ***“on water”effect facilitates polymerization in aqueous media better than in organic solvents,and its mechanism is deciphered through experimental data and theoretical *** participates in the reaction and reduces the energy barrier to some ***,polymerization makes it possible for aromatic amine with low reactivity to be *** using this strategy,polymers with high molecular weights can be obtained in high yields(up to 95.4%).They show good thermal stability and high *** can be *** polymers with tetraphenylethylene moieties show aggregation-induced emission and can be used as materials for generating photopatterns and visualizing agents for specific staining of lysosome in living cells.

关键词： “on water”effect click polymerization aromatic amine photodegradation specific lysosome-staining

A Simple Approach to Bioconjugation at Diverse Levels: Metal-Free Click Reactions of Activated Alkynes with Native Groups of Biotargets without Prefunctionalization

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Research 2018年第1期2018卷 172-183页

作者： Xianglong Hu Xueqian Zhao benzhao he Zheng Zhao Zheng Zheng Pengfei Zhang Xiujuan Shi Ryan T.K.Kwok Jacky W.Y.Lam Anjun Qin Ben Zhong Tang Department of Chemistry Hong Kong Branch of Chinese National EngineeringResearch Center for Tissue Restoration and ReconstructionInstitute of Advanced StudyState Key Laboratory of Molecular NanoscienceDivision of Life Science and Diversion of Biomedical EngineeringTe Hong Kong University of Science and TechnologyClear Water BayKowloonHong KongChina Ministry of Education Key Laboratory of Laser Life Science&Institute of Laser Life Science College of BiophotonicsSouth China Normal UniversityGuangzhou 510631China HKUST-Shenzhen Research Institute Shenzhen 518057China NSFC Center for Luminescence from Molecular Aggregates SCUT-HKUST Joint Research InstituteState Key Laboratory of Luminescent Materials and DevicesSouth China University of TechnologyGuangzhou 510640China

Te efcient bioconjugation of functional groups/molecules to targeted matrix and bio-related species drives the great development of material science and biomedicine,while the dilemma of metal catalysis,uneasy premodifcation,and limited reaction efciency in traditional bioconjugation has restricted the booming development to some ***,we provide a strategy for metal-free click bioconjugation at diverse levels based on activated *** a proof-of-concept,the abundant native groups including amine,thiol,and hydroxyl groups can directly react with activated alkynes without any modifcation in the absence of metal *** this strategy,high-efcient modifcation and potential functionalization can be achieved for natural polysaccharide,biocompatible polyethylene glycol(PEG),synthetic polymers,cell penetrating peptide,protein,fast whole-cell mapping,and even quick diferentiation and staining of Gram-positive bacteria,***,current metal-free click bioconjugation strategy based on activated alkynes is promising for the development of quick fuorescence labeling and functional modifcation of many targets and can be widely applied towards the fabrication of complex biomaterials and future in vivo labeling and detection.

关键词： proof catalysis biomaterials

AIE材料合成、表征及其在防伪印刷中的应用

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大学化学 2023年第4期38卷 134-142页

作者：何亚珂张思怡黎雅珊何本钊北京师范大学珠海校区先进材料研究中心广东珠海519085

荧光防伪印刷技术即是将特殊的荧光印刷油墨融合到标识上,并借助额外的激发光才能找到加密信息,从而起到防伪作用。荧光防伪多在膜或固态下使用,因此需要荧光油墨在这些状态下具有强的发光性质。聚集诱导发光(Aggregation-Induced Emiss... 详细信息

荧光防伪印刷技术即是将特殊的荧光印刷油墨融合到标识上,并借助额外的激发光才能找到加密信息,从而起到防伪作用。荧光防伪多在膜或固态下使用,因此需要荧光油墨在这些状态下具有强的发光性质。聚集诱导发光(Aggregation-Induced Emission,AIE)分子是一类在单分子状态下发光较弱甚至不发光而在聚集状态下表现出强烈发光的分子。而水杨醛席夫碱分子作为一类合成简单、荧光强度高的典型AIE分子,具备刺激响应荧光机制,其在酸碱环境下表现出不同的荧光特性使得这一类分子在防伪印刷领域有突出的表现。本论文通过水杨醛与胺的亲核加成反应一步制备水杨醛席夫碱AIE分子,并进一步展示其在防伪印刷中的应用;通过对该分子在不同环境下的表征,阐明其AIE特性和刺激响应荧光机制在防伪印刷应用中的作用。本实验原料易得、安全、成本低廉,所需仪器常规,符合实验教学要求,通过本实验训练,学生不仅掌握了席夫碱类化合物的制备方法,同时也学习了水杨醛席夫碱分子的刺激响应荧光在防伪印刷中的应用。结合课堂教学和拓展阅读,使学生进一步了解防伪印刷产品的特性以及设计思路。

关键词：聚集诱导发光防伪印刷席夫碱荧光分子综合化学实验

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LAMINAR FLUID FLOW IN heLICAL ELLIPTICAL PIPE

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Journal of Hydrodynamics 2000年第2期12卷 62-71页

作者： Zhang, Jinsuo Zhang, benzhao Zhejiang Univ Hangzhou China

By means of an orthogonal curvilinear coordinate system and the solution of complete N-S equations, the flow in a helical elliptical duct was analyzed by the perturbation method. The first-order solutions of the stream function, the axial velocity and the velocity of secondary flow were obtained. The effects of torsion, curvature and axial pressure gradient on the secondary flow were discussed. The torsion has first-order effect on the secondary flow in a helical elliptical pipe, and the secondary flow is dominated by torsion when the axial pressure gradient is small. For increasing gradient the secondary flow is eventually dominated by the effect due to curvature. The fact that the torsion has no effect on fluid flow in a helical pipe with a circular cross section was also confirmed. The most important conclusion is that the flow in a helical elliptical pipe to the first order can be obtained as a combination of the flow in a toroidal pipe and the flow in a twisted pipe.

关键词： Flow of fluids Laminar flow Perturbation techniques Torsional stress

FINITE LAYER MODEL FOR 2-D TheRMAL DENSITY FLOW IN A CHANNEL

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Journal of Hydrodynamics 1996年第2期8卷 85-91页

作者： Zhang, benzhao Sheng, Xinrong Zhejiang Univ Hangzhou China

The mathematical equations of 2-D thermal density flow in a channel were developed and a finite layer numerical model was established. In the direction of y, a cubic spline approximations were used for u and θ, and linear interpolation were used for du/dx and dθ/dx. The integration of differential equations along the direction of y was made with the subdomain scheme of weighted residual method. In the direction of x, the boundary value problem of differential equations was converted into an initial value problem. It is then solved by shooting method. An effective method for choosing and amending shooting multipoint initial values have been presented. The vertical distribution of u and θ at each x-section were also obtained.

关键词： Computer simulation Density of liquids Mathematical models Numerical analysis Thermal effects Viscous flow