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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 friendliness.Organic 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 water.However,reports about click polymerization in water have been rare.Herein,click polymerization of activated alkyne and aromatic amine in aqueous media is developed.The“on water”effect facilitates polymerization in aqueous media better than in organic solvents,and its mechanism is deciphered through experimental data and theoretical calculations.Water participates in the reaction and reduces the energy barrier to some extent.Besides,polymerization makes it possible for aromatic amine with low reactivity to be linked.By 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 refractivity.They can be photodegraded.The 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

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AZIDE-ALKYNE click polymerization:AN UPDATE

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Chinese Journal of Polymer Science 2012年第1期30卷 1-15页

作者： Hong-kun Li Jing-zhi Sun An-jun Qin Ben Zhong Tang MOE Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University Hangzhou 310027 China Department of Chemistry Institute of Molecular Functional Materials The Hong Kong University of Science ＆ Technology Clear Water Bay Kowloon Hong Kong China

The great achievements of click chemistry have encouraged polymer scientists to use this reaction in their field. This review assembles an update of the advances of using azide-alkyne click polymerization to prepare functional polytriazoles（PTAs） with linear and hyperbranched structures.The Cu（I）-mediated click polymerization furnishes 1,4-regioregular PTAs,whereas,the metal-free click polymerization of propiolates and azides produces PTAs with 1,4-regioisomer contents up to 90%.The PTAs display advanced functions,such as aggregation-induced emission,thermal stability,biocompatibility and optical nonlinearity.

关键词： click polymerization Azide Alkyne Polytriazole Functionality

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Synthesis of Functional Hyperbranched Poly(methyltriazolylcarboxylate)s by Catalyst-free click polymerization of Butynoates and Azides

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Chinese Journal of Polymer Science 2020年第11期38卷 1171-1177,I0005页

作者： Mu-Ning Lang Wei-Wen Chi Ting Han Qing-Zhen Zhao Hong-Kun Li Ben Zhong Tang Yong-Fang Li State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials Laboratory of Advanced Optoelectronic MaterialsCollege of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhou 215123China State Key Laboratory of Luminescent Materials and Devices Key Laboratory of Luminescence from Molecular Aggregates of Guangdong ProvinceCenter for Aggregation-Induced EmissionSouth China University of TechnologyGuangzhou 510640China Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and ReconstructionThe Hong Kong University of Science&TechnologyClear Water BayKowloonHong KongChina

Azide-alkyne click polymerization has become a powerful tool for polymer synthesis.However,the click polymerization between internal alkynes and azides is rarely utilized to prepare functional polymers.In this work,the polymerization reactions of activated internal alkyne monomers of tris(2-butynoate)s(1)with tetraphenylethene-containing diazides(2)were performed in dimethylformamide(DMF)under simple heating,affording four hyperbranched poly(methyltriazolylcarboxylate)s(hb-PMTCs)with high molecular weights(A4W up to 2.4 x 104)and regioregularities(up to 83.9%)in good yields.The hb-PMTCs are soluble in common organic solvents,and thermally stable with 5%weight loss temperatures up to 400℃.They are non-emissive in dilute solution,but become highly emissive in aggregated state,exhibiting aggregationinduced emission characteristics.The polymers can generate fluorescent photopatterns with high resolution,and can work as fluorescent sensors to detect nitroaromatic explosive with high sensitivity.

关键词： click polymerization Hyperbranched polymer Aggregation-induced emission Explosive detection Photopattern

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X-yne click polymerization

Aggregate

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Aggregate 2023年第5期4卷 12-33页

作者： Xinyao Fu Anjun Qin Ben Zhong Tang State Key Laboratory of Luminescent Materials and Devices Guangdong Provincial Key Laboratory of Luminescence from Molecular AggregatesSouth China University of TechnologyGuangzhouChina Center for Aggregation-Induced Emission AIE InstituteSouth China University of TechnologyGuangzhouChina School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhenGuangdongChina Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration and Reconstruction The Hong Kong University of Science&TechnologyKowloonHong KongChina

Alkyne-based click polymerizations have been nurtured into a powerful synthetic technique for the preparation of new polymers with advanced structures and versatile properties.Among them,the emerging thiol-yne,hydroxyl-yne,and amino-yne click polymerizations have made remarkable progress from reactions to applications.These polymerizations avoid the usage of inherently dangerous monomers and are safer to operate than the classical azide-alkyne click polymerization(AACP),making them more prospective for diverse applications.To greatly promote the new alkyne-based click polymerizations beyond AACP,a new concept of“X-yne click polymerization”is proposed to unify them,where“X”denotes the monomers that can react with alkynes under mild reaction conditions,including thiols,alcohols,amines,and other promising ones.In this review,we mainly present a brief account of the progress of X-yne click polymerization and discuss in detail the challenges and opportunities in this field.

关键词： alkyne-based polymerization click chemistry click polymerization

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Mainchain Semifluorinated Polymers with Ultra High Molecular Weight via Reaction-enhanced Reactivity of Intermediate(RERI) Mechanism

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Chinese Journal of Polymer Science 2023年第5期41卷 760-767,I0009页

作者： Jia-Sheng Wu Wang-Meng Hou Zhi-Jia Liu Yi Shi Yong-Ming Chen School of Materials Science and Engineering Key Laboratory for Polymeric Composite and Functional Materials of Ministry of EducationSun Yat-Sen UniversityGuangzhou 510006China

Achieving the linear polymers with high molecular weight via step-growth polymerization of A2 and B2 monomers is significantly limited by the requirement of strict stoichiometry of two monomers when the reactivity of A and B groups are not changed during the polymerization.Herein,a unique step-growth polymerization based on copper-catalyzed azide-alkyne cycloaddition(CuAAC)with reactionenhanced reactivity of intermediate(RERI)mechanism was developed for the preparation of mainchain semifluorinated polymers with high molecular weight.The CuAAC polymerization of bis-alkynyl-terminated fluorinated monomers(A2)and 2,2-bis(azidomethyl)propane-1,3-diyl bis(2-methylpropanoate)(BiAz,B2)with RERI effect at different stoichiometric ratio was systematically investigated.The results indicated that the semifluorinated polymers with ultrahigh molecular weight,Mw,MALLS>106 g/mol,could be efficiently synthesized by using excess molar of BiAz monomers.The resultant high-molecular-weight semifluorinated polymers show good thermostability and high hydrophobicity.In addition,the glass transition temperature(Tg)of these mainchain semifluorinated polymers could be tuned conveniently due to the bis-alkynyl-terminated comonomers could be consumed completely when excessive BiAz monomers were used in this this step-growth polymerization.

关键词： Semifluorinated polymers click polymerization Step-growth polymerization

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Thiol-Yne click polymerization

Thiol-Yne Click Polymerization

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2011年全国高分子学术论文报告会

作者： Cathy K.W.Jim Department of Chemistry The Hong Kong University of Science ＆ TechnologyClear Water BayKowloonHong KongChina

＜正＞Azide-alkyne click polymerization has been a hot research topic because of the important role in plays in polymer chemistry and macromolecular engineering.We have endeavored to develop this new polymerization te... 详细信息

关键词： click polymerization regioselectivity stereoselectivity functional polymers

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Synthesis and thermal properties of polyethylene glycol/glucose solid-solid phase change materials for thermal energy storage

Synthesis and thermal properties of polyethylene glycol/gluc...

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中国化学会第七届全国热分析动力学与热动力学学术会议

作者： Yucao Zhu Chaowei Huang Rong Ji Yongpeng Xia Sheng Wei Qingfeng Zhang Huanzhi Zhang Fen Xu Lixian Sun Guangxi Key Laboratory of Information Materials Guilin University of Electronic Technology

＜正＞To improve the phase change behavior and thermal stability of phase change materials（PCMs）,a novel solid-solid PCMs（SSPCMs） was designed and synthetized via click polymerization using poly（ethylene glycol） as soft segment and glucose as hard segment.The chemical structure,crystalline properties,thermal energy storage properties and thermal stability of the synthesized SSPCMs were characterized by Fourier transform infrared spectroscopy（FT-IR）,X-ray diffraction （XRD）,differential scanning calorimetry（DSC） and thermogravimetric analysis（TGA）.

关键词： thermal stability solid-solid phase change materials polyethylene glycol click polymerization

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