基于多重氢键的纳米粘接技术
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摘要
粘接现象普遍存在于自然界的各个方面,粘接剂更是伴随着人类文明的进步而不断发展演化。目前,相关的粘接理论仍然不够成熟。本文以超分子化学的角度,从分子水平出发,通过分析基于多重氢键的纳米粘接剂及粘接技术的作用原理,总结近年来的研究情况,以期为今后粘接剂和粘接技术的研究提供一个新的角度。
Adhesion phenomenon existed in all aspects of nature. Adhesive was developing and evolving with the progress of human civilization. At present,the relevant bonding theory was still not perfect. In this paper,the research progress in recent years was summarized by analyzing the mechanism of nano-adhesive based on multiple hydrogen bonds and bonding technology from the perspective of supramolecular chemistry,in order to provide a new perspective for the future research of adhesive and bonding technology.
Adhesion phenomenon existed in all aspects of nature. Adhesive was developing and evolving with the progress of human civilization. At present,the relevant bonding theory was still not perfect. In this paper,the research progress in recent years was summarized by analyzing the mechanism of nano-adhesive based on multiple hydrogen bonds and bonding technology from the perspective of supramolecular chemistry,in order to provide a new perspective for the future research of adhesive and bonding technology.
引文
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[32] MCGHEE A M,KILNER C,WILSON A J. Conformer independent heterodimerisation of linear arrays using three hydrogen bonds[J].Chemical Communications,2008,3(3):344-346.
[33] DJURDJEVIC S,LEIGH D A,MCNAB H,et al.Extremely strong and readily accessible AAA-DDD triple hydrogen bond complexes[J]. Journal of the American Chemical Society,2007,129(3):476-477.
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[35] MARTIN A M,BUTLER R S,GHIVIRIGA I,et al.Selfcomplementary purines by quadruple hydrogen bonding[J].Chemical Communications,2006,42(42):4413-4415.
[36] SIJBESMA R P,BEIJER F H,BRUNSVELD L,et al.Reversible polymers formed from self-complementary monomers using quadruple hydrogen bonding[J].Science,1998,29(10):1601-1604.
[37] CORBIN P S,ZIMMERMAN S C.Self-association without regard to prototropy. a heterocycle that forms extremely stable quadruply hydrogen-bonded dimers[J]. Journal of the American Chemical Society,1998,120(37):9710-9711.
[38] LIGTHART G B,OHKAWA H,SIJBESMA R P,et al.Complementary quadruple hydrogen bonding in supramolecular copolymers[J]. Journal of the American Chemical Society,2005,127(3):810-811.
[39] ANDERSON C A,TAYLOR P G,ZELLER M A,et al.Room temperature, copper-catalyzed amination of bromonaphthyridines with aqueous ammonia[J]. The Journal of Organic Chemistry,2010,75(14):4848-4851.
[40] PARK T,ZIMMERMAN S C,NAKASHIMA S.A highly stable quadruply hydrogen-bonded heterocomplex useful for supramolecular polymer blends[J]. Journal of the American Chemical Society,2005,127(18):6520-6521.
[41] PARK T,TODD E M,NAKASHIMA S,et al.A quadruply hydrogen bonded heterocomplex displaying high-fidelity recognition[J].Journal of the American Chemical Society,2005,127(51):18133-18142.
[42] ONG H C,ZIMMERMAN S C.Higher affinity quadruply hydrogen-bonded complexation with 7-deazaguanine urea[J].Organic Letters,2006,8(8):1589-1592.
[43] KUYKENDALL D W,ANDERSON C A,ZIMMERMAN S C. Hydrogen-bonded DeUG x DAN heterocomplex:structure and stability and a scalable synthesis of DeUG with reactive functionality[J]. Organic Letters,2009,11(1):61-64.
[44] BLIGHT B A,HUNTER C A,LEIGH D A,et al. An AAAA-DDDD quadruple hydrogen-bond array[J]. Nature Chemistry,2011,3(3):244-248.
[45] LIU X,ZHANG Q,GAO G.Bioinspired adhesive hydrogels tackified by nucleobases[J].Advanced Functional Materials,2017,27(44):1-6.
[46] ISHIKAWA N,FURUTANI M,ARIMITSU K. Adhesive materials utilizing a thymine-adenine interaction and thymine photodimerization[J]. ACS Macro Letters,2015,4(7):741-744.
[47] CYRUS A,ANDERSON,AMANDA R,et al.High-affinity DNA base analogs as supramolecular,nanoscale promoters of macroscopic adhesion[J]. Journal of the American Chemical Society,2013,135(19):7288-7295.
[2] ONUSSEIT H,WEFRINGHAUS R,DREEZEN G,et al.Adhesives,1. General[M]//Ullmann′s Encyclopedia of Industrial Chemistry,2010.
[3] POCIUS A V.Adhesion and Adhesives Technology(Third Edition)[M]//Adhesion and Adhesives Technology,2012.
[4] PETRIE E M. Handbook of Adhesives and Sealants,McGraw-Hill:Chicago,2007.
[5] SIVAKOVA S,ROWAN S J.Nucleobases as supramolecular motifs[J].Chemical Society Reviews,2005,34(1):9-21.
[6] BINDER W H,ZIRBS R. Supramolecular polymers and networks with hydrogen bonds in the main-and side-chain.Advances in Polymer Science,2007,207:1-78.
[7] DE GREEF T F A,SMULDERS M M J,WOLFFS M,et al.Supramolecularpolymerization[J].ChemicalReviews,2009,109:5687-5754.
[8] NORSTEN T B,JEOUNG E,THIBAULT R J,et al.Specific hydrogen-bond-mediated recognition and modification of surfaces using complementary functionalized polymers[J].Langmuir,2003,19(17):7089-7093.
[9] VISWANATHAN K,OZHALICI H,ELKINS C L,et al.Multiple hydrogen bonding for reversible polymer surface adhesion[J].Langmuir,2006,22(3):1099-1105.
[10] XU H,HONG R,LU T,et al. Recognition-directed orthogonal self-assembly of polymers and nanoparticles on patterned surfaces[J]. Journal of the American Chemical Society,2006,128(10):3162-3163.
[11] HARADA A,KOBAYASHI R,TAKASHIMA Y,et al.Macroscopic self-assembly through molecular recognition.[J].Nature Chemistry,2011,3(1):34-37.
[12] KERSEY F R,LEE G,MARSZALEK P,et al.Surface-tosurfacebridgesformedbyreversiblyassembledpolymers[J].Journal of the American Chemical Society,2004,126(10):3038-3039.
[13] ZOU S,SCHNHERR H,VANCSO G J.Force spectroscopy of quadruple H-bonded dimers by AFM:Dynamic bond rupture and molecular time-temperature superposition[J].Journal of the American Chemical Society,2005,127(32):11230-11231.
[14] PARK T,ZIMMERMAN S C,NAKASHIMA S.A highly stable quadruply hydrogen-bonded heterocomplex useful for supramolecular polymer blends[J].Journal of the American Chemical Society,2005,127(18):6520-6521.
[15] PARK T,ZIMMERMAN S C. Interplay of fidelity,binding strength,and structure in supramolecular polymers[J].Journal of the American Chemical Society,2006,128(44):14236-14237.
[16] FELDMAN K E,KADE M J,DE GREEF T F A,et al.Polymers with multiple hydrogen-bonded end groups and their blends[J].Macromolecules,2008,41(13):4694-4700.
[17] KUO S W,CHENG R S.DNA-like interactions enhance the miscibility of supramolecular polymer blends[J].Polymer,2009,50(1):177-188.
[18] LI Y,PARK T,QUANSAH J K,et al.Synthesis of a redoxresponsive quadruple hydrogen-bonding unit for applications in supramolecular chemistry[J].Journal of the American Chemical Society,2011,133(43):17118-17121.
[19] WONG C H,ZIMMERMAN S C.Orthogonality in organic,polymer,and supramolecular chemistry:from Merrifield to click chemistry[J].Chemical Communications,2013,49(17):1679-1695.
[20] STUART M A C,HUCK W T S,GENZER J,et al.Emerging applications of stimuli-responsive polymer materials[J].Nature Materials,2010,9(2):101-113.
[21] MAULDIN T C,KESSLER M.Self-healing polymers and composites[J]. Metallurgical Reviews,2010,55(6):317-346.
[22] WOJTECKI R J,MEADOR M A,ROWAN S J.Using the dynamic bond to access macroscopically responsive structurally dynamic polymers[J].Nature Materials,2011,10(1):14-27.
[23] PRINS L J, REINHOUDT D, TIMMERMAN P.Noncovalent synthesis using hydrogen bonding[J].Angewandte Chemie International Edition,2010,40(13):2382-2426.
[24] JORGENSEN W L,PRANATA J.Importance of secondary interactionsintriplyhydrogenbondedcomplexes:Guaninecytosine vs uracil-2,6-diaminopyridine[J].Journal of the American Chemical Society,1990,112(5):2008-2010.
[25] MURRAY T J,ZIMMERMAN S C.New triply hydrogen bonded complexes with highly variable stabilities[J].Journal of the American Chemical Society,1992,114(10):4010-4011.
[26] BLIGHT B A,CAMARACAMPOS A,DJURDJEVIC S,et al.AAA-DDD triple hydrogen bond complexes[J].Journal of the American Chemical Society,2009,131(39):14116-14122.
[27] S?NTJENS S H M,SIJBESMA R P,VAN GENDEREN M H P,et al. Stability and lifetime of quadruply hydrogen bonded 2-ureido-4[1H]-pyrimidinone dimers[J].Journal of the American Chemical Society,2000,122(31):7487-7493.
[28] BEIJER F H,SIJBESMA R P,VEKEMANS J A J M,et al.Hydrogen bonded complexes of diaminopyridines and diaminotriazines:Opposite effect of acylation on complex stabilities[J].Cheminform,2010,28(4):6371-6380.
[29] KYOGOKU Y,LORD R C,RICH A. The effect of substituents on the hydrogen bonding of adenine and uracil derivatives[J].Proceedings of the National Academy of Sciences,1967,57(2):250-257.
[30] FIASCHI A,RIZZUTO N,PUXEDDU P.Chiral separation of heterocyclic drugs by HPLC:solute-stationary phase base-pairinteractions[J].Cheminform,1986,17(41):3310-3318.
[31] HISAMATSU Y,FUKUMI Y,SHIRAI N,et al. Fivemembered heterocyclic ureas suitable for the donordonor-acceptor hydrogen-bonding modules[J].Tetrahedron Letters,2008,49(12):2005-2009.
[32] MCGHEE A M,KILNER C,WILSON A J. Conformer independent heterodimerisation of linear arrays using three hydrogen bonds[J].Chemical Communications,2008,3(3):344-346.
[33] DJURDJEVIC S,LEIGH D A,MCNAB H,et al.Extremely strong and readily accessible AAA-DDD triple hydrogen bond complexes[J]. Journal of the American Chemical Society,2007,129(3):476-477.
[34] BRUNSVELD L,VEKEMANS J A,HIRSCHBERG J H,etal.Hierarchical formation of helical supramolecular polymers via stacking of hydrogen-bonded pairs in water[J].Proceedings of the National Academy of Sciences,2002,99(8):4977-4982.
[35] MARTIN A M,BUTLER R S,GHIVIRIGA I,et al.Selfcomplementary purines by quadruple hydrogen bonding[J].Chemical Communications,2006,42(42):4413-4415.
[36] SIJBESMA R P,BEIJER F H,BRUNSVELD L,et al.Reversible polymers formed from self-complementary monomers using quadruple hydrogen bonding[J].Science,1998,29(10):1601-1604.
[37] CORBIN P S,ZIMMERMAN S C.Self-association without regard to prototropy. a heterocycle that forms extremely stable quadruply hydrogen-bonded dimers[J]. Journal of the American Chemical Society,1998,120(37):9710-9711.
[38] LIGTHART G B,OHKAWA H,SIJBESMA R P,et al.Complementary quadruple hydrogen bonding in supramolecular copolymers[J]. Journal of the American Chemical Society,2005,127(3):810-811.
[39] ANDERSON C A,TAYLOR P G,ZELLER M A,et al.Room temperature, copper-catalyzed amination of bromonaphthyridines with aqueous ammonia[J]. The Journal of Organic Chemistry,2010,75(14):4848-4851.
[40] PARK T,ZIMMERMAN S C,NAKASHIMA S.A highly stable quadruply hydrogen-bonded heterocomplex useful for supramolecular polymer blends[J]. Journal of the American Chemical Society,2005,127(18):6520-6521.
[41] PARK T,TODD E M,NAKASHIMA S,et al.A quadruply hydrogen bonded heterocomplex displaying high-fidelity recognition[J].Journal of the American Chemical Society,2005,127(51):18133-18142.
[42] ONG H C,ZIMMERMAN S C.Higher affinity quadruply hydrogen-bonded complexation with 7-deazaguanine urea[J].Organic Letters,2006,8(8):1589-1592.
[43] KUYKENDALL D W,ANDERSON C A,ZIMMERMAN S C. Hydrogen-bonded DeUG x DAN heterocomplex:structure and stability and a scalable synthesis of DeUG with reactive functionality[J]. Organic Letters,2009,11(1):61-64.
[44] BLIGHT B A,HUNTER C A,LEIGH D A,et al. An AAAA-DDDD quadruple hydrogen-bond array[J]. Nature Chemistry,2011,3(3):244-248.
[45] LIU X,ZHANG Q,GAO G.Bioinspired adhesive hydrogels tackified by nucleobases[J].Advanced Functional Materials,2017,27(44):1-6.
[46] ISHIKAWA N,FURUTANI M,ARIMITSU K. Adhesive materials utilizing a thymine-adenine interaction and thymine photodimerization[J]. ACS Macro Letters,2015,4(7):741-744.
[47] CYRUS A,ANDERSON,AMANDA R,et al.High-affinity DNA base analogs as supramolecular,nanoscale promoters of macroscopic adhesion[J]. Journal of the American Chemical Society,2013,135(19):7288-7295.