点击化学反应及其在材料保护领域的应用
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摘要
点击化学反应是一种模块化合成新物质的方法,具有环保、高产率、反应条件温和等特点,在材料保护和材料表面修饰等领域展现出极大的发展空间。点击化学反应可以简单高效地合成聚合物,使其在防护性涂层材料制备中具有重要地位。通过利用点击化学反应可以检测材料的损伤情况,并实现材料失效的可视化,这为防护性材料的开发提供了全新的研究思路。点击化学反应还可以高效地往缓蚀剂分子中引入不同的官能团,从而得到具有不同特性的分子结构,进而有效地提高缓蚀剂的缓蚀效率。另外点击化学反应能够实现材料表面特定部位的局部修饰,具有可定量、可定位的特点。但是在材料保护领域得到应用的点击反应数量仍然很少,仍需对点击反应的催化剂和反应条件进行研究。简要地介绍了点击化学基本概念以及特点,重点探讨了其在材料保护领域的应用,主要包括防护性材料的制备、缓蚀剂合成、表面处理等方面,总结了点击化学技术目前在材料保护应用中存在的问题,并对其发展前景进行了评述。
Click chemistry reaction is a method to compound new substances and shows great prospects in material protection and material surface modification due to features of environmental friendliness, high yield and moderate reaction conditions. The work briefly introduces basic concept and features of click chemistry, and emphatically discusses its application in material protection field, including protective material preparation, corrosion inhibition synthesis and surface treatment. The current problems of click chemistry used in material protection are summarized and the development prospect is reviewed. The polymer can be synthesized simply and efficiently by click chemistry and then occupy a leading position in the preparation of protective coating materials. The damage of material can be detected by click chemistry reaction and the failure of the material can be visualized. This provides a new research path for the application of protective materials. Click chemistry can also efficiently introduce different functional groups into the inhibitor molecules so that different molecular structures can be obtained.This can effectively improve the inhibition efficiency of inhibitors. In addition, click chemistry reaction can realize the local modification on the specific part of the material surface. It has the quantifiable and position-able characteristics. However, the number of click chemistry applied in the field of material protection is still very small, and it is still necessary to study the catalyst and reaction conditions of click chemistry.
Click chemistry reaction is a method to compound new substances and shows great prospects in material protection and material surface modification due to features of environmental friendliness, high yield and moderate reaction conditions. The work briefly introduces basic concept and features of click chemistry, and emphatically discusses its application in material protection field, including protective material preparation, corrosion inhibition synthesis and surface treatment. The current problems of click chemistry used in material protection are summarized and the development prospect is reviewed. The polymer can be synthesized simply and efficiently by click chemistry and then occupy a leading position in the preparation of protective coating materials. The damage of material can be detected by click chemistry reaction and the failure of the material can be visualized. This provides a new research path for the application of protective materials. Click chemistry can also efficiently introduce different functional groups into the inhibitor molecules so that different molecular structures can be obtained.This can effectively improve the inhibition efficiency of inhibitors. In addition, click chemistry reaction can realize the local modification on the specific part of the material surface. It has the quantifiable and position-able characteristics. However, the number of click chemistry applied in the field of material protection is still very small, and it is still necessary to study the catalyst and reaction conditions of click chemistry.
引文
[1]KOLB H C, FINN M G, SHARPLESS K B. Click chemistry:Diversechemicalfunctionfromafewgoodreactions[J].Angewandtechemieinternationaledition,2001,40(11):2004-2021.
[2]COLLMANJP,DEVARAJNK,CHIDSEYCED.“Clicking”functionalityontoelectrodesurfaces[J].Langmuir, 2004, 20(4):1051-1053.
[3]彭奇鸣.硫桥杯芳烃-四硫富瓦烯衍生物的合成及性质研究[D].郑州:郑州大学, 2011.PENGQi-ming.Synthesisofthiacalixarene-tetrathiafulvalene assemblies and the study of these properties[D].Zhengzhou:Zhengzhou University, 2011.
[4]LUTZ J F. Copper-free azide-alkyne cycloadditions:New insights and perspectives[J]. Angewandte chemie international edition, 2008, 47(12):2182-2184.
[5]HUISGENR.Cheminformabstract:1,3-dipolar cycloaddition-introduction,survey,mechanism[J].Cheminform,1985, 16(18):176-179.
[6]邱素艳,高森,林振宇,等.点击化学最新进展[J].化学进展, 2011, 23(4):637-648.QIU Su-yan, GAO Sen, LIN Zhen-yu, et al. Advances in clickchemistry[J].Progressinchemistry,2011,23(4):637-648.
[7]ROSTOVTSEV V V, GREEN L G, FOKIN V V, et al. A stepwise huisgen cycloaddition process:Copper(I)-catalyzed regioselective“ligation”ofazidesandterminalalkynes[J].Angewandtechemieinternationaledition,2002,114(14):2708-2711.
[8]LINS,GOSSAINP,NAUMANNJA,etal.Efficient synthetic approach to linear dasatinib-DNA conjugates by click chemistry[J]. Bioconjugate chemistry, 2016, 27(10):2575-2579.
[9]LID,XIEJ,ZHOUW,etal.Clickchemistry-mediated cycliccleavageofmetalion-dependentDNAzymesfor amplifiedandcolorimetricdetectionofhumanserum copper(II)[J].Analyticalandbioanalyticalchemistry,2017, 409(27):1-7.
[10]PUNETHA VD,RANAS, YOOHJ, etal.Functionalizationofcarbonnanomaterialsforadvancedpolymer nanocomposites:AcomparisonstudybetweenCNTand grapheme[J]. Progress in polymer science, 2017, 67:1-47.
[11]LINL,SUNH,ZHANGK,etal.Novelaffinitymembranes with macrocyclic spacer arms synthesized via click chemistryforlysozymebinding[J].Journalofhazardous materials, 2017, 327:97-107.
[12]ASAIH,OCHIAIH,ELOUALIS.Biopharmaceutical discovery by organic synthesis[J]. Trends in glycoscience and glycotechnology, 2017, 29(168):E63-E68.
[13]XI W, SCOTT T F, KLOXIN C J, et al. Click chemistry in materials science[J]. Advanced functional materials, 2014,24(18):2572-2590.
[14]左育静.基于巯基“点击”反应合成有机硅荧光材料及性能研究[D].济南:山东大学, 2017.ZUOYu-jing.Synthesisandpropertiesoforganosilicon luminescentmaterialsviathiol"click"chemistry[D].Jinan:Shandong University, 2017.
[15]HOYLE C E, BOWMAN C N. Thiol-ene click chemistry[J].Angewandtechemieinternationaledition,2010,49(9):1540-1573.
[16]HELMSB,MYNARJL,HAWKERCJ.Dendronized linearpolymersvia“clickchemistry”[J].Journalofthe american chemical society, 2004, 126(46):15020-15021.
[17]KILLOPSKL,CAMPOSLM,HAWKERCJ.Robust,efficient,andorthogonalsynthesisofdendrimersviathiol-ene"click"chemistry[J].Journaloftheamerican chemical society, 2008, 130(15):5062-5064.
[18]SCHULZE B, SCHUBERT U S. Beyond click chemistrysupramolecularinteractionsof1,2,3-triazoles[J].Chemical society reviews, 2014, 43(8):2522-2571.
[19]IRENING,NARAYANR,BASAKP,etal.Poly(thiourethane-urethane)-ureaasanticorrosioncoatingswith impressiveopticalproperties[J].Polymer,2016, 97:370-379.
[20]KANTHETI S, NARAYAN R, RAJU K. Development of moisturecurepolyurethane-ureacoatingsusing1,2,3-triazole core hyperbranched polyesters[J]. Journal of coatings technology and research, 2013, 10(5):609-619.
[21]KANTHETI S, NARAYAN R, RAJU K. Click chemistry engineeredhyperbranchedpolyurethane-ureaforfunctionalcoatingapplications[J].Industrial&engineering chemistry research, 2014, 53(20):8357-8365.
[22]KANTHETIS,GADDAMRR,NARAYANR,etal.Hyperbranchedpolyoldecoratedcarbonnanotubeby clickchemistryforfunctionalpolyurethaneureahybrid composites[J]. RSC advances, 2014, 4(47):24420-24427.
[23]SYKAMK,DONEMPUDIS.Novelmultifunctional hybrid diallyl ether monomer via azide alkyne click reaction as crosslinking agent in protective coatings[J]. Polymer, 2015, 62:60-69.
[24]VASILIU S, KAMPE B, THEIL F, et al. Insights into the mechanismofpolymercoatingself-healingusingraman spectroscopy[J].Appliedspectroscopy,2014,68(5):541-548.
[25]NEUMANNS,D?HLERD,STR?HLD,etal.Chelation-assisted CuAAC in star-shaped polymers enables fast self-healingatlowtemperatures[J].Polymerchemistry,2016, 7(13):2342-2351.
[26]MICHAELP,D?HLERD,BINDERWH.Improving autonomousselfhealingvia combinedchemical/physical principles[J]. Polymer, 2015, 69:216-227.
[27]ZHAO Y, D?HLER D, LV L P, et al. Facile phase-separation approach toencapsulatefunctionalizedpolymersin core-shellnanoparticles[J].Macromolecularchemistry&physics, 2014, 215(2):198-204.
[28]HERBST F, D?HLER D, MICHAEL P, et al. Self-healing polymersviasupramolecularforces[J].Macromolecular rapid communications, 2013, 34(3):203-220.
[29]D?HLERD,RANAS,RUPPH,etal.Qualitativesensingofmechanicaldamagebyafluorogenic"click"reaction[J].Chemicalcommunications,2016,52(74):11076-11079.
[30]NIAAS,RANAS,D?HLERD,etal.Nanocomposites viaadirectgraphene-promoted“click”-reaction[J].Polymer, 2015, 79:21-28.
[31]YATVIN J, BROOKS K, LOCKLIN J. SuFEx click:New materialsfromSOxFandsilylethers[J].Chemistry—A european journal, 2016, 22(46):16348-16354.
[32]D?HLERD,MICHAELP,BINDERWH.Cu AACbasedclickchemistryinself-healingpolymers[J].Accounts of chemical research, 2017, 50(10):2610-2620.
[33]GONZáLEZR,ESPINOZAA,NEGRóNGE,etal.Multicomponent click synthesis of new 1,2,3-triazole derivativesofpyrimidinenucleobases:Promisingacidic corrosion inhibitors for steel[J]. Molecules, 2013, 18(12):15064-15079.
[34]NEGRóN G E, GONZáLEZ R, ANGELES D. Synthesis ofnew1,2,3-triazolederivativesofuracilandthymine withpotentialinhibitoryactivityagainstacidiccorrosion of steels[J]. Molecules, 2013, 18(4):4613-4627.
[35]ZHANGHL,HEXP,DENGQ,etal.Researchonthe structure-surfaceadsorptiveactivityrelationshipsoftriazolyl glycolipid derivatives for mild steel in HCl[J]. Carbohydrate research, 2012, 354:32-39.
[36]DENGQ,DINGNN,WEIXL,etal.Identificationof diverse1,2,3-triazole-connectedbenzylglycoside-serine/threonineconjugatesaspotentcorrosioninhibitorsfor mild steel in HCl[J]. Corrosion science, 2012, 64:64-73.
[37]DENG Q, HE X P, SHI H W, et al. Concise CuI-catalyzed azide-alkyne1,3-dipolarcycloadditionreactionligation remarkablyenhancesthecorrosioninhibitivepotencyof natural amino acids for mild steel in HCl[J]. Industrial&engineering chemistry research, 2012, 51(21):7160-7169.
[38]ZHANG T, CAO S, QUAN H, et al. Synthesis and corrosioninhibitionperformanceofalkyltriazolederivatives[J]. Research on chemical intermediates, 2015, 41(5):2709-2724.
[39]RAMAGANTHAN B, GOPIRAMAN M, OLASUNKANMI LO,etal.Synthesizedphoto-cross-linkingchalconesas novel corrosion inhibitors for mild steel in acidic medium:experimental, quantum chemical and monte carlo simulation studies[J]. RSC advances, 2015, 5(94):76675-76688.
[40]WANGQ,HAWKERC.Towardafewgoodreactions:Celebrating click chemistry’s first decade[J]. Chemistry—An asian journal, 2011, 6(10):2568-2569.
[41]COLLMAN J P, HOSSEINI A, EBERSPACHER T A, et al.Selectiveanodicdesorptionforassemblyofdifferent thiolmonolayerson theindividualelectrodesofan array[J]. Langmuir, 2009, 25(11):6517-6521.
[42]GU L, XUE Q, PENG S, et al. A novel and facile strategy toinhibitcorrosion:Thiol-clicksynthesisofpolythiols and their skinning on a metal surface to form super thick protective films[J]. Polymer chemistry, 2016, 7(3):625-632.
[43]XIAO X, XIE W, YE Z. Preparation of corrosion-resisting superhydrophobicsurfaceonaluminiumsubstrate[J].Surface engineering, 2018, 56:1-7.
[44]HOUK,ZENGY,ZHOUC,etal.Facilegenerationof robustPOSS-basedsuperhydrophobicfabricsviathioleneclickchemistry[J].Chemicalengineeringjournal,2018, 332:150-159.
[45]CAMPOSMA,PAULUSSEJM,ZUILHOFH.Functional monolayers on oxide-free silicon surfaces via thioleneclickchemistry[J].Chemicalcommunications,2010,46(30):5512-5514.
[46]张昭,陈宇,刘姣,等.一种有机硅改性丙烯酸防污涂料的研究[J].装备环境工程, 2016, 13(4):1-7.ZHANGZhao,CHENYu,LIUJiao,etal.Antifouling coating made of organic silicon modified acrylic resin[J].Equipment enviromental engineering, 2016, 13(4):1-7.
[47]LIJ,LIL,DUX,etal.Reactivesuperhydrophobicsurface and its photoinduced disulfide-ene and thiol-ene(Bio)functionalization[J]. Nano letters, 2014, 15(1):675-681.
[48]MARTIN K L, NYQUIST Y, BURNETT E K, et al. Sur-facegraftingoffunctionalizedpoly(thiophene)susing thiol-ene click chemistry for thin film stabilization[J]. Acs applied materials&interfaces, 2016, 8(44):30543-30551.
[49]WANG Y, YU Y, ZHANG J, et al. Click-assembling triazolemembraneoncoppersurfaceviaone-stepor two-stepsandtheircorrosioninhibitionperformance[J].Applied surface science, 2018, 427:1120-1128.
[50]YUY,WANGY,LIJ,etal.Insituclick-assembling monolayersoncoppersurfacewithenhancedcorrosion resistance[J]. Corrosion science, 2016, 113:133-144.
[51]LUONGND,SINHLH,JOHNANSSONLS,etal.Functionalgraphenebythiol-eneclickchemistry[J].Chemistry—A european journal, 2015, 21(8):3183-3186.
[52]COLLINSJ,XIAOZ,M?LLNERM,etal.Theemergence of oxime click chemistry and its utility in polymer science[J]. Polymer chemistry, 2016, 7(23):3812-3826.
[53]CASTROV,RODRíGUEZH,ALBERICIOF.Cu AAC:Anefficientclickchemistryreactiononsolidphase[J].Acs combinatorial science, 2016, 18(1):1-14.
[54]WANG X, HUANG B, LIU X, et al. Discovery of bioactivemoleculesfromCuAACclick-chemistry-basedcombinatorial libraries[J]. Drug discovery today, 2016, 21(1):118-132.
[55]ALONSO F, MOGLIE Y, RADIVOY G. Copper nanoparticlesinclickchemistry[J].Accountsofchemicalresearch, 2015, 48(9):2516-2528.
[56]BROOKS K, YATVIN J, MCNITT C D, et al. Multifunctional surface manipulation using orthogonal click chemistry[J]. Langmuir the ACS journal of surfaces&colloids,2016, 32(26):6600-6605.
[2]COLLMANJP,DEVARAJNK,CHIDSEYCED.“Clicking”functionalityontoelectrodesurfaces[J].Langmuir, 2004, 20(4):1051-1053.
[3]彭奇鸣.硫桥杯芳烃-四硫富瓦烯衍生物的合成及性质研究[D].郑州:郑州大学, 2011.PENGQi-ming.Synthesisofthiacalixarene-tetrathiafulvalene assemblies and the study of these properties[D].Zhengzhou:Zhengzhou University, 2011.
[4]LUTZ J F. Copper-free azide-alkyne cycloadditions:New insights and perspectives[J]. Angewandte chemie international edition, 2008, 47(12):2182-2184.
[5]HUISGENR.Cheminformabstract:1,3-dipolar cycloaddition-introduction,survey,mechanism[J].Cheminform,1985, 16(18):176-179.
[6]邱素艳,高森,林振宇,等.点击化学最新进展[J].化学进展, 2011, 23(4):637-648.QIU Su-yan, GAO Sen, LIN Zhen-yu, et al. Advances in clickchemistry[J].Progressinchemistry,2011,23(4):637-648.
[7]ROSTOVTSEV V V, GREEN L G, FOKIN V V, et al. A stepwise huisgen cycloaddition process:Copper(I)-catalyzed regioselective“ligation”ofazidesandterminalalkynes[J].Angewandtechemieinternationaledition,2002,114(14):2708-2711.
[8]LINS,GOSSAINP,NAUMANNJA,etal.Efficient synthetic approach to linear dasatinib-DNA conjugates by click chemistry[J]. Bioconjugate chemistry, 2016, 27(10):2575-2579.
[9]LID,XIEJ,ZHOUW,etal.Clickchemistry-mediated cycliccleavageofmetalion-dependentDNAzymesfor amplifiedandcolorimetricdetectionofhumanserum copper(II)[J].Analyticalandbioanalyticalchemistry,2017, 409(27):1-7.
[10]PUNETHA VD,RANAS, YOOHJ, etal.Functionalizationofcarbonnanomaterialsforadvancedpolymer nanocomposites:AcomparisonstudybetweenCNTand grapheme[J]. Progress in polymer science, 2017, 67:1-47.
[11]LINL,SUNH,ZHANGK,etal.Novelaffinitymembranes with macrocyclic spacer arms synthesized via click chemistryforlysozymebinding[J].Journalofhazardous materials, 2017, 327:97-107.
[12]ASAIH,OCHIAIH,ELOUALIS.Biopharmaceutical discovery by organic synthesis[J]. Trends in glycoscience and glycotechnology, 2017, 29(168):E63-E68.
[13]XI W, SCOTT T F, KLOXIN C J, et al. Click chemistry in materials science[J]. Advanced functional materials, 2014,24(18):2572-2590.
[14]左育静.基于巯基“点击”反应合成有机硅荧光材料及性能研究[D].济南:山东大学, 2017.ZUOYu-jing.Synthesisandpropertiesoforganosilicon luminescentmaterialsviathiol"click"chemistry[D].Jinan:Shandong University, 2017.
[15]HOYLE C E, BOWMAN C N. Thiol-ene click chemistry[J].Angewandtechemieinternationaledition,2010,49(9):1540-1573.
[16]HELMSB,MYNARJL,HAWKERCJ.Dendronized linearpolymersvia“clickchemistry”[J].Journalofthe american chemical society, 2004, 126(46):15020-15021.
[17]KILLOPSKL,CAMPOSLM,HAWKERCJ.Robust,efficient,andorthogonalsynthesisofdendrimersviathiol-ene"click"chemistry[J].Journaloftheamerican chemical society, 2008, 130(15):5062-5064.
[18]SCHULZE B, SCHUBERT U S. Beyond click chemistrysupramolecularinteractionsof1,2,3-triazoles[J].Chemical society reviews, 2014, 43(8):2522-2571.
[19]IRENING,NARAYANR,BASAKP,etal.Poly(thiourethane-urethane)-ureaasanticorrosioncoatingswith impressiveopticalproperties[J].Polymer,2016, 97:370-379.
[20]KANTHETI S, NARAYAN R, RAJU K. Development of moisturecurepolyurethane-ureacoatingsusing1,2,3-triazole core hyperbranched polyesters[J]. Journal of coatings technology and research, 2013, 10(5):609-619.
[21]KANTHETI S, NARAYAN R, RAJU K. Click chemistry engineeredhyperbranchedpolyurethane-ureaforfunctionalcoatingapplications[J].Industrial&engineering chemistry research, 2014, 53(20):8357-8365.
[22]KANTHETIS,GADDAMRR,NARAYANR,etal.Hyperbranchedpolyoldecoratedcarbonnanotubeby clickchemistryforfunctionalpolyurethaneureahybrid composites[J]. RSC advances, 2014, 4(47):24420-24427.
[23]SYKAMK,DONEMPUDIS.Novelmultifunctional hybrid diallyl ether monomer via azide alkyne click reaction as crosslinking agent in protective coatings[J]. Polymer, 2015, 62:60-69.
[24]VASILIU S, KAMPE B, THEIL F, et al. Insights into the mechanismofpolymercoatingself-healingusingraman spectroscopy[J].Appliedspectroscopy,2014,68(5):541-548.
[25]NEUMANNS,D?HLERD,STR?HLD,etal.Chelation-assisted CuAAC in star-shaped polymers enables fast self-healingatlowtemperatures[J].Polymerchemistry,2016, 7(13):2342-2351.
[26]MICHAELP,D?HLERD,BINDERWH.Improving autonomousselfhealingvia combinedchemical/physical principles[J]. Polymer, 2015, 69:216-227.
[27]ZHAO Y, D?HLER D, LV L P, et al. Facile phase-separation approach toencapsulatefunctionalizedpolymersin core-shellnanoparticles[J].Macromolecularchemistry&physics, 2014, 215(2):198-204.
[28]HERBST F, D?HLER D, MICHAEL P, et al. Self-healing polymersviasupramolecularforces[J].Macromolecular rapid communications, 2013, 34(3):203-220.
[29]D?HLERD,RANAS,RUPPH,etal.Qualitativesensingofmechanicaldamagebyafluorogenic"click"reaction[J].Chemicalcommunications,2016,52(74):11076-11079.
[30]NIAAS,RANAS,D?HLERD,etal.Nanocomposites viaadirectgraphene-promoted“click”-reaction[J].Polymer, 2015, 79:21-28.
[31]YATVIN J, BROOKS K, LOCKLIN J. SuFEx click:New materialsfromSOxFandsilylethers[J].Chemistry—A european journal, 2016, 22(46):16348-16354.
[32]D?HLERD,MICHAELP,BINDERWH.Cu AACbasedclickchemistryinself-healingpolymers[J].Accounts of chemical research, 2017, 50(10):2610-2620.
[33]GONZáLEZR,ESPINOZAA,NEGRóNGE,etal.Multicomponent click synthesis of new 1,2,3-triazole derivativesofpyrimidinenucleobases:Promisingacidic corrosion inhibitors for steel[J]. Molecules, 2013, 18(12):15064-15079.
[34]NEGRóN G E, GONZáLEZ R, ANGELES D. Synthesis ofnew1,2,3-triazolederivativesofuracilandthymine withpotentialinhibitoryactivityagainstacidiccorrosion of steels[J]. Molecules, 2013, 18(4):4613-4627.
[35]ZHANGHL,HEXP,DENGQ,etal.Researchonthe structure-surfaceadsorptiveactivityrelationshipsoftriazolyl glycolipid derivatives for mild steel in HCl[J]. Carbohydrate research, 2012, 354:32-39.
[36]DENGQ,DINGNN,WEIXL,etal.Identificationof diverse1,2,3-triazole-connectedbenzylglycoside-serine/threonineconjugatesaspotentcorrosioninhibitorsfor mild steel in HCl[J]. Corrosion science, 2012, 64:64-73.
[37]DENG Q, HE X P, SHI H W, et al. Concise CuI-catalyzed azide-alkyne1,3-dipolarcycloadditionreactionligation remarkablyenhancesthecorrosioninhibitivepotencyof natural amino acids for mild steel in HCl[J]. Industrial&engineering chemistry research, 2012, 51(21):7160-7169.
[38]ZHANG T, CAO S, QUAN H, et al. Synthesis and corrosioninhibitionperformanceofalkyltriazolederivatives[J]. Research on chemical intermediates, 2015, 41(5):2709-2724.
[39]RAMAGANTHAN B, GOPIRAMAN M, OLASUNKANMI LO,etal.Synthesizedphoto-cross-linkingchalconesas novel corrosion inhibitors for mild steel in acidic medium:experimental, quantum chemical and monte carlo simulation studies[J]. RSC advances, 2015, 5(94):76675-76688.
[40]WANGQ,HAWKERC.Towardafewgoodreactions:Celebrating click chemistry’s first decade[J]. Chemistry—An asian journal, 2011, 6(10):2568-2569.
[41]COLLMAN J P, HOSSEINI A, EBERSPACHER T A, et al.Selectiveanodicdesorptionforassemblyofdifferent thiolmonolayerson theindividualelectrodesofan array[J]. Langmuir, 2009, 25(11):6517-6521.
[42]GU L, XUE Q, PENG S, et al. A novel and facile strategy toinhibitcorrosion:Thiol-clicksynthesisofpolythiols and their skinning on a metal surface to form super thick protective films[J]. Polymer chemistry, 2016, 7(3):625-632.
[43]XIAO X, XIE W, YE Z. Preparation of corrosion-resisting superhydrophobicsurfaceonaluminiumsubstrate[J].Surface engineering, 2018, 56:1-7.
[44]HOUK,ZENGY,ZHOUC,etal.Facilegenerationof robustPOSS-basedsuperhydrophobicfabricsviathioleneclickchemistry[J].Chemicalengineeringjournal,2018, 332:150-159.
[45]CAMPOSMA,PAULUSSEJM,ZUILHOFH.Functional monolayers on oxide-free silicon surfaces via thioleneclickchemistry[J].Chemicalcommunications,2010,46(30):5512-5514.
[46]张昭,陈宇,刘姣,等.一种有机硅改性丙烯酸防污涂料的研究[J].装备环境工程, 2016, 13(4):1-7.ZHANGZhao,CHENYu,LIUJiao,etal.Antifouling coating made of organic silicon modified acrylic resin[J].Equipment enviromental engineering, 2016, 13(4):1-7.
[47]LIJ,LIL,DUX,etal.Reactivesuperhydrophobicsurface and its photoinduced disulfide-ene and thiol-ene(Bio)functionalization[J]. Nano letters, 2014, 15(1):675-681.
[48]MARTIN K L, NYQUIST Y, BURNETT E K, et al. Sur-facegraftingoffunctionalizedpoly(thiophene)susing thiol-ene click chemistry for thin film stabilization[J]. Acs applied materials&interfaces, 2016, 8(44):30543-30551.
[49]WANG Y, YU Y, ZHANG J, et al. Click-assembling triazolemembraneoncoppersurfaceviaone-stepor two-stepsandtheircorrosioninhibitionperformance[J].Applied surface science, 2018, 427:1120-1128.
[50]YUY,WANGY,LIJ,etal.Insituclick-assembling monolayersoncoppersurfacewithenhancedcorrosion resistance[J]. Corrosion science, 2016, 113:133-144.
[51]LUONGND,SINHLH,JOHNANSSONLS,etal.Functionalgraphenebythiol-eneclickchemistry[J].Chemistry—A european journal, 2015, 21(8):3183-3186.
[52]COLLINSJ,XIAOZ,M?LLNERM,etal.Theemergence of oxime click chemistry and its utility in polymer science[J]. Polymer chemistry, 2016, 7(23):3812-3826.
[53]CASTROV,RODRíGUEZH,ALBERICIOF.Cu AAC:Anefficientclickchemistryreactiononsolidphase[J].Acs combinatorial science, 2016, 18(1):1-14.
[54]WANG X, HUANG B, LIU X, et al. Discovery of bioactivemoleculesfromCuAACclick-chemistry-basedcombinatorial libraries[J]. Drug discovery today, 2016, 21(1):118-132.
[55]ALONSO F, MOGLIE Y, RADIVOY G. Copper nanoparticlesinclickchemistry[J].Accountsofchemicalresearch, 2015, 48(9):2516-2528.
[56]BROOKS K, YATVIN J, MCNITT C D, et al. Multifunctional surface manipulation using orthogonal click chemistry[J]. Langmuir the ACS journal of surfaces&colloids,2016, 32(26):6600-6605.