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Recyclable Cu nanoparticle catalyzed azide-alkyne click polymerization

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Science China Chemistry 2019年第8期62卷 1017-1022页

作者： Yizhao Chen Benzhao He Anjun Qin Ben Zhong Tang State Key Laboratory of Luminescent Materials and Devices Center 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 Reconstruction Institute for Advanced StudyDepartment of Chemical and Biological EngineeringThe Hong Kong University of Science & Technology Hong KongChina

The Cu(I)-catalyzed alkyne-azide cycloaddition(CuAAC) has been developed into a powerful polymerization reaction for the synthesis of new polytriazoles with versatile properties. However, research on recyclable and reusable copper catalyst for click polymerization to meet the requirement of green chemistry was rarely reported. Copper nanoparticles were reported to be capable catalysts for CuAAC. Replacing conventional copper catalyst with copper nanoparticles may realize the recycle and reuse of the copper catalyst in click polymerization. In this paper, copper nanoparticles were prepared and used as an effective catalyst for click polymerization, and soluble polytriazoles with high molecular weights were obtained in excellent yields under optimized reaction conditions. Importantly, the copper nanoparticles can be recycled and reused for up to 11 times for the click polymerization. Moreover, introducing aggregation-induced emission(AIE)-active moiety of tetraphenylethylene into the monomers makes the resultant polymers retain the AIE feature. This work not only provides an efficient recyclable catalytic system for the azide-alkyne click polymerization, but also might inspire polymer chemists to use recyclable copper species to catalyze other polymerizations.

关键词： click polymerization Cu nanoparticles recyclability reusability

Synthesis of Alkyne-functionalized Polymers via Living Anionic Polymerization and Investigation of Features during the Post-“thiol-yne” click Reaction

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Chinese Journal of Polymer Science 2019年第9期37卷 841-850页

作者： Lin-Can Yang Li Han Hong-Wei Ma Pi-Bo Liu He-Yu Shen Chao Li Song-Bo Zhang Yang Li Department of Polymer Science and Engineering School of Chemical Engineering Dalian University of Technology

"Thiol-yne" click reaction has already been widely applied in synthesis and modification of new polymer structures or novel materials due to its specific features. However, in most studies, only chain-end strategy was employed when using the di-addition feature of thiol-yne reaction, thus the in-chain di-addition strategy could endow us with a broader space to develop the synthesis of advanced polymers. Therefore, in this paper, the features of in-chain mono and di-addition were investigated when modifying the alkynefunctionalized polymers to prepare grafted polymers via thiol-yne click reaction. The results showed that it is almost impossible to obtain the in-chain di-adducts even under excess feeding of chain-end thiol-functionalized grafts, while only the in-chain mono-adducts could be obtained efficiently. Further researches investigated that the controlled grafting could be encountered when carrying out the thiol-yne click reaction between chain-end alkyne-functionalized polystyrenes and chain-end thiol-functionalized polystyrenes under proper feedings. Therefore, the effect of steric?hindrance might be the primary reason for the alternative grafting via thiol-yne click reaction between in-chain and chain-end alkyne-functionalized polymers.

关键词： Alkyne-functionalized polymers In-chain di-addition Thiol-yne click reaction Living anionic polymerization

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海豚不同个体间发声信号差异性分析

海洋与渔业 2024年第1期 70-71页

作者：王一帆袁世鹏张吉昌刘滨青岛海洋科技中心中国水产科学研究院黄海水产研究所

海豚在长期进化过程中形成了一套依靠声波进行通信、定位和环境识别的声纳系统。该声呐系统定位精度高、识别能力强,可以在能见度低的水下环境中快速发现和定位目标,其水下探测与识别效率远远超过人造设备。根据海豚声信号的用途不同,... 详细信息

海豚在长期进化过程中形成了一套依靠声波进行通信、定位和环境识别的声纳系统。该声呐系统定位精度高、识别能力强,可以在能见度低的水下环境中快速发现和定位目标,其水下探测与识别效率远远超过人造设备。根据海豚声信号的用途不同,国际上通常将海豚的发声信号分为回声定位信号(click)、通信交流信号(Whistle)、应急突发信号(Burst pulse)等。

关键词：突发信号声信号交流信号环境识别声纳系统水下环境 click 声呐系统

Modular synthesis of a block copolymer with a cleavable linkage via “click” chemistry

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Science China Chemistry 2010年第5期53卷 1127-1132页

作者： Fu, Yu Liu, GuoJun Research Centre for Molecular Science and Engineering Northeastern University Shenyang 110004 China Department of Chemistry Queen's University Ontario Canada

A diblock copolymer poly(ethylene glycol)-block-polystyrene or PEG-b-PS with an olefinic double bond at the PEG and PS junction has been prepared by modular synthesis via"click"chemistry.This involved the synthesis of PS by atom transfer radical polymerization and the nucleophilic substitution of the terminal bromide group with azide to yield azide-terminated PS. PEG with an alkynyl terminal group was prepared from reacting carboxyl-end-functionalized PEG with 4-hydroxybut-2-enyl prop-2-ynyl succinate,which contained an alkynyl group as well as an olefin group.The PS and PEG polymers were linked via the 1,3-dipolar cycloaddition of the end azide and alkyne groups.The obtained copolymer was characterized by 1H NMR spectroscopy and size exclusion chromatography(SEC).SEC analysis indicated that the diblock copolymer produced could be readily cleaved by ozonolysis to regenerate the constituent homopolymers.

关键词： modular synthesis cleavable block copolymer click chemistry ATRP

Functionalized Polyphosphoester via Living Ring-opening Polymerization and Photochemical Thiol-ene click Reaction

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Chemical Research in Chinese Universities 2019年第2期35卷 340-344页

作者： WANG Ying WANG Qiliao HOU Liman ZHOU Mingdong DONG Dewen ZHANG Ning School of Chemistry and Materials Science Liaoning Shihua UniversityFushun 113001P.RChina CAS Key Laboratory of High-performance Synthetic Rubber and Its Composite Materials Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022P.R.China University of Science and Technology of China Hefei 230026P.R.China

Poly(ethylene phosphonate)was synthesized via the living ring-opening polymerization of cyclic phos-phonate monomer catalyzed by organocatalyst.The pendant vinyl ftmctionalities were employed to perform the pho-tochemical click reactions wi&tMols.We demonstrated that both small thiol molecules and macromolecular thiols could be efficiently coupled into the PPE side chains,enabling the rapid and efficient functionalization of polyphos-phoesters(PPE).

关键词： Cyclic phosphonate Ring-opening polymerization Thiol-ene click reaction Post modification

Development of Cardanol-Based Polyol via click Chemistry and Crosslinking with Melamine Formaldehyde Resin for Coating Applications

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Journal of Renewable Materials 2018年第4期6卷 438-449页

作者： Kunal Wazarkar Anagha Sabnis Department of Polymer and Surface Engineering Institute of Chemical TechnologyNathalal Parekh MargMatunga(E)Mumbai 400019India

The research work presented in this article deals with the synthesis of cardanol-based polyol and its curing with hexabutoxymethyl melamine(HBMM)for application in coatings.Cardanol-based polyol was prepared via thiol-ene click reaction using thioglycerol.Unsaturation present in the long chain of cardanol was successfully utilized to synthesize polyol via thiol-ene coupling.The reaction was carried out between cardanol and thioglycerol in the presence of Irgacure 184(photoinitiator)and 1,8-Diazabicyclo[5.4.0]undec-7-ene(catalyst)under UV light for 12 h at 80°C.After completion of the reaction,one mole of thioglycerol was successfully added across the double bond of a fatty chain of cardanol and confirmed by Fourier transform infrared spectroscopy(FTIR)and proton nuclear magnetic resonance spectroscopy and hydroxyl and iodine values were determined.Furthermore,the polyol thus prepared was cured with commercial HBMM in various proportions,such as 1:0.6,1:0.8 and 1:1,on an equivalent basis.The coatings were then characterized for mechanical,chemical,optical,thermal and anticorrosive properties.It was observed that coatings exhibited excellent performance properties as compared to that of its acrylic counterpart.

关键词： CNSL click chemistry HBMM crosslinker anticorrosive sustainable

Synthesis of disk-rod-disk liquid crystal trimers by using click chemistry

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Science China Chemistry 2010年第5期53卷 1133-1140页

作者： Yu, WenHao Nie, ShiChang Bai, YueFeng Jing, Yang Wang, BiQin Hu, Ping Zhao, KeQing College of Chemistry and Material Science Sichuan Normal University Chengdu 610066 China

A series of disk-rod-disk liquid crystal trimers were synthesized.CuI-NEt3 catalyzed alkyne azide cycloaddition in toluene at room temperature connected two triphenylene discogens to a biphenyl rod-shaped mesogen.The trimers were characterized by using 1H NMR,IR,and high resolution mass spectrometry.The mesomorphic properties were investigated using polarized optical microscopy(POM) ,differential scanning calorimetry(DSC) ,and wide-angle X-ray diffraction.The results showed that the trimers exhibited rectangular columnar mesophase(Colr) .The length of the flexible spacer connecting the three segments has prominent influence on the phase transition temperatures of the trimers.

关键词： liquid crystal trimer triphenylene rectangular columnar mesophase click chemistry copper(Ⅰ) catalyzed alkyne azide cycloaddition

Synthesis of PEGylated Salicylaldehyde Azine via Metal-free click Chemistry for Cellular Imaging Application

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Chemical Research in Chinese Universities 2019年第5期35卷 929-936页

作者： CHEN Xin XIAO Chunsheng CHEN Xuesi Key Laboratory of Polymer Ecomaterials Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022P.R.China University of Chinese Academy of Sciences Beijing 100049P.R.China Jilin Biomedical Polymers Engineenug Laboratory Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022P.R.China

Ill tliis work, two kinds of PEGylated salicylaldehyde azine(SA) polymers were prepared and investigated for cellular imaging applications. First, a diazido derivative of SA was synthesized and subsequently PEGylated with polyethylene glycol monomethyl ether(mPEG) by metal-free azide-alkyne 1,3-dipolar cycloaddition reaction. The formed triazole group in niPEG-SA was then converted into cationic triazolium group by N-alkylation reaction. Botli the synthesized polymers, niPEG-SA and N-alkylated niPEG-SA, showed good dispersibility in water, but differences in self-assembly of nanostructures. The niPEG-SA with triazole groups self-assembled into micelles, while the N-alkylated mPEG-SA with triazolium groups sell-assembled into vesicles. Furthemiore, mPEG-SA and N-alkylated niPEG?SA naiioparticles showed bright fluorescence due to the aggregation of AIE-active SA molecules in the nanoparticles and could be successfully used as fluorescent naiioprobes for bioimaging applications in HeLa cancer cells. Finally, both the synthesized polymers showed minimal cytotoxicity and low hemolytic activity. Therefore, these PEGylated SA polymers proved to be promising bioimaging nanoprobes or traceable dnig delivery vehicles.

关键词： click chemistry Aggregation-induced emission nanoprobe PEGylation Bioimagiiig Self-assembly

One-pot synthesis of hyperbranched poly(amido amine) clicked with a sugar shell via Michael addition polymerization and thiol click reaction

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Science China Chemistry 2010年第8期53卷 1663-1668页

作者： YU ZhiQiang,CUI MengMeng,YAN JunJie & YOU YeZi CAS Key Lab of Soft Matter Chemistry Department of Polymer Science and Engineering,University of Science and Technology of China,Hefei 230026,China CAS Key Lab of Soft Matter Chemistry Department of Polymer Science and Engineering University of Science and Technology of China Hefei China

This paper reports the production of glycopolymers via a simple and flexible method.A novel glycopolymer with a hyperbranched poly(amido amine) core and a sugar shell (HPAA-GLc) was synthesized by using thiol-ene click reaction via facile one-pot method.Hyperbranched poly(amido amine) with vinyl terminals was first synthesized by Michael addition polymerization of N,N'-methylene bisacrylamide (MBA) with 1-(2-aminoethyl) piperazine (AEPZ).Subsequently,thiol-ene click reaction between vinyl units of hyperbranched poly(amido amine) and thio-glucose was performed in situ.Based on the NMR result,all the vinyl groups reacted with thiol-glucose in 120 min.Strong photoluminescence emission was observed from the aqueous solution of HPAA-GLc.

关键词： thiol-ene click reaction glycopolymers hyperbranched poly(amido amine) photoluminescence