硫醇-烯/炔点击化学制备有机/无机杂化材料
Synthesis of Organic/Inorganic Hybrid Materials via Thiol-Ene/Yne Click Chemistry
有机/无机杂化材料因其独特、优异的结构和性能已经成为目前材料领域的研究热点,硫醇-烯/炔点击化学是近年发展起来的一类新型点击化学,以其反应条件温和、速率快、产率高、产物容易分离以及高度选择性等优点受到国内外研究者的广泛关注。本文综述了近年来硫醇-烯/炔点击化学制备有机/无机杂化材料的研究进展,重点介绍了利用硫醇-烯/炔点击化学制备硅类、碳类、金属及金属氧化物类有机/无机杂化材料,并归纳了这些有机/无机杂化材料在生物医用、环境保护、光电材料等方面的应用,最后展望了硫醇-烯/炔点击化学制备有机/无机杂化材料未来的发展方向。
During last several decades, organic/inorganic hybrid materials have been used widely in many fields due to their excellent structure and performance. Thiol-ene/yne click chemistry, a new type of click chemistry, is of great interest because of its mild reaction conditions, fast reaction rate, high yield, easy post-treatment and high selectivity for the obtained products. Therefore, synthesis of high-performance organic/inorganic hybrid materials via thiol-ene/yne click chemistry is one of the hot topics of novel material research. In this review, the recent research progress of organic/inorganic hybrid materials synthesized by thiol-ene/yne click chemistry is discussed. Synthesis of silicon-, carbon-, metal- and metal oxide-based organic/inorganic hybrid materials via thiol-ene/yne click chemistry is highlighted. In addition, the applications of these hybrid materials in the fields of biomedical materials, environment protection and photoelectric materials are summarized. Finally, the development trend and future prospects of organic/inorganic hybrid materials synthesized by thiol-ene/yne click chemistry are presented.
Contents
1 Introduction
2 Organic/inorganic hybrid materials synthesized by thiol-ene/yne click chemistry
2.1 Synthesis of silicon-based organic/inorganic hybrid materials
2.2 Synthesis of carbon-based organic/inorganic hybrid materials
2.3 Synthesis of metal- and metal oxide-based organic/inorganic hybrid materials
3 Application of organic/inorganic hybrid materials synthesized by thiol-ene/yne click chemistry
3.1 Biomedical materials
3.2 Environmental protection
3.3 Photoelectric materials
3.4 Other application
4 Conclusions and outlook
有机/无机杂化材料
organic/inorganic hybrid materials
[1] 刘华蓉(Liu H R), 葛学武(Ge X W), 倪永红(Ni Y H), 叶强(Ye Q), 张广祥(Zhang G X), 张志成(Zhang Z C), 张曼维(Zhang M W). 化学进展(Progress in Chemistry), 2001, 13(5): 403.
[2] Masarudin M J, Yusoff K, Rahim R A, Hussein M Z. Nanotechnology, 2009, 20(4): 045602.
[3] Wu J, Mather P T. Polym. Rev., 2009, 49(1): 25.
[4] Filion T M, Xu J W, Prasad M L, Song J. Biomaterials, 2011, 32(4): 985.
[5] Di Noto V, Piga M, Lavina S, Negro E, Yoshida K, Ito R, Furukawa T. Electrochim. Acta, 2010, 55(4): 1431.
[6] Di Noto V, Piga M, Piga L, Polizzi S, Negro E. J. Power Sources, 2008, 178(2): 561.
[7] Zhang Y W, Ye Z B. Macromolecules, 2008, 41(17): 6331.
[8] Monticelli O, Cavallo D, Bocchini S, Frache A, Carniato F, Tonelotto A. J. Polym. Sci. Part A: Polym. Chem., 2011, 49(22): 4794.
[9] Carlos L D, Ferreira R A S, Bermudez V D, Ribeiro S J L. Adv. Mater., 2009, 21(5): 509.
[10] 浦鸿汀(Pu H T), 秦深(Qin S), 杨正龙(Yang Z L), 袁俊杰(Yuan J J), 万德成(Wan D C). 功能材料(Journal of Functional Materials), 2007, 38(9): 1499.
[11] Tanaka K, Inafuku K, Chujo Y. Chem. Commun., 2010, 46(24): 4378.
[12] Tran-Thi T H, Dagnelie R, Crunairez S, Nicole L. Chem. Soc. Rev., 2011, 40(2): 621.
[13] Wolfbeis O S. J. Mater. Chem., 2005, 15(27/28): 2657.
[14] Zuo X, Yu S, Xu X, Bao R, Xu J, Qu W. J. Membrane Sci., 2009, 328(1/2): 23.
[15] Vaysse C, Guerlou-Demourgues L, Duguet E, Delmas C. Inorg. Chem., 2003, 42(15): 4559.
[16] Yeh J M, Liou S J, Lai M C, Chang Y W, Huang C Y, Chen C P, Jaw J H, Tsai T Y, Yu Y H. J. Appl. Polym. Sci., 2004, 94(5): 1936.
[17] Park N G, Ryu K S, Park Y J, Kang M G, Kim D K, Kang S G, Kim K M, Chang S H. J. Power Sources, 2002, 103(2): 273.
[18] Vaysse C, Guerlou-Demourgues L, Delmas C, Duguet E. Macromolecules, 2004, 37(1): 45.
[19] Jurmanovic S, Kordic S, Steinberg M D, Steinberg I M. Thin Solid Films, 2010, 518(8): 2234.
[20] Valliant E M, Jones J R. Soft Matter, 2011, 7(11): 5083.
[21] Kolb H C, Finn M G, Sharpless K B. Angew. Chem. Int. Edit., 2001, 40(11): 2004.
[22] Hoyle C E, Lee T Y, Roper T. J. Polym. Sci. Part A: Polym. Chem., 2004, 42(21): 5301.
[23] Fairbanks B D, Scott T F, Kloxin C J, Anseth K S, Bowman C N. Macromolecules, 2009, 42(1): 211.
[24] Bhairamadgi N S, Gangarapu S, Campos M A C, Paulusse J M J, van Rijn C J M, Zuilhof H. Langmuir, 2013, 29(14): 4535.
[25] Harant A W, Khire V S, Thibodaux M S, Bowman C N. Macromolecules, 2006, 39(4): 1461.
[26] Jia X Y, Jiang X S, Liu R, Yin J. Polymer, 2010, 51(20): 4511.
[27] Schulz C, Nowak S, Frohlich R, Ravoo B J. Small, 2012, 8(4): 569.
[28] Li G L, Wan D, Neoh K G, Kang E T. Macromolecules, 2010, 43(24): 10275.
[29] Li G L, Xu L Q, Tang X Z, Neoh K G, Kang E T. Macromolecules, 2010, 43(13): 5797.
[30] Hata E, Mitsube K, Momose K, Tomita Y. Opt. Mater. Express, 2011, 1(2): 207.
[31] Li Y, Dong X H, Guo K, Wang Z, Chen Z, Wesdemiotis C, Quirk R P, Zhang W B, Cheng S Z. ACS Macro Lett., 2012, 1(7): 834.
[32] Gao Y, Eguchi A, Kakehi K, Lee Y C. Org. Lett., 2004, 6(20): 3457.
[33] Lo Conte M, Staderini S, Chambery A, Berthet N, Dumy P, Renaudet O, Marra A, Dondoni A. Org. Biomol. Chem., 2012, 10(16): 3269.
[34] Liu D D, Yu B, Jiang X S, Yin J. Langmuir, 2013, 29(17): 5307.
[35] Iehl J, Nierengarten J F. Chem. Commun., 2010, 46(23): 4160.
[36] Iskin B, Yilmaz G, Yagci Y. Chem. Eur. J., 2012, 18(33): 10254.
[37] Yang Z L, Pu H T, Yuan J J, Wan D C, Liu Y S. Chem. Phys. Lett., 2008, 465(1/3): 73.
[38] Temel G, Uygun M, Arsu N. Polym. Bull., 2013, 70(12): 3563.
[39] Prichard T D, Singh S S, Chawla N, Vogt B D. Polymer, 2013, 54(3): 1130.
[40] Yang Z L, Shi X J, Yuan J J, Pu H T, Liu Y S. Appl. Surf. Sci., 2010, 257(1): 138.
[41] Salavagione H J, Gomez M A, Martinez G. Macromolecules, 2009, 42(17): 6331.
[42] Luo J, Jiang S S, Liu R, Zhang Y J, Liu X Y. Electrochim. Acta, 2013, 96: 103.
[43] Castelaín M, Martínez G, Ellis G, Salavagione H J. Chem. Commun., 2013, 49(79): 8967.
[44] Castelaín M, Martínez G, Marco C, Ellis G, Salavagione H J. Macromolecules, 2013, 46(22): 8980.
[45] Van Berkel K Y, Hawker C J. J.Polym. Sci. Part A: Polym. Chem., 2010, 48(7): 1594.
[46] Li G L, Xu L Q, Neoh K G, Kang E T. Macromolecules, 2011, 44(7): 2365.
[47] Hayashi K, Ono K, Suzuki H, Sawada M, Moriya M, Sakamoto W, Yogo T. Chem. Mater., 2010, 22(12): 3768.
[48] Rutledge R D, Warner C L, Pittman J W, Addleman R S, Engelhard M, Chouyyok W, Warner M G. Langmuir, 2010, 26(14): 12285.
[49] Faccini F, Fric H, Schubert U, Wendel E, Tsetsgee O, Muller K, Bertagnolli H, Venzo A, Gross S. J. Mater. Chem., 2007, 17(31): 3297.
[50] Sangermano M, Gross S, Priola A, Rizza G, Sada C. Macromol. Chem. Phys., 2007, 208(23): 2560.
[51] Chen Y, Wu M, Wang K, Chen B, Yao S, Zou H, Nie L. J. Chromatogr. A, 2011, 1218(44): 7982.
[52] Wu J T, Huang C H, Liang W C, Wu Y L, Yu J S, Chen H Y. Macromol. Rapid. Comm., 2012, 33(10): 922.
[53] Oberleitner B, Dellinger A, Deforet M, Galtayries A, Castanet A S, Semetey V. Chem. Commun., 2013, 49(16): 1615.
[54] Escorihuela J, Banuls M J, Puchades R, Maquieira A. Chem. Commun., 2012, 48(15): 2116.
[55] Mai T B, Tran T N, Islam M R, Park J M, Lim K T. J. Mater. Sci., 2013, 48(19): 1.
[56] He H B, Li B, Dong J P, Lei Y Y, Wang T L, Yu Q W, Feng Y Q, Sun Y B. ACS Appl. Mater. Interfaces, 2013, 5(16): 8058.
[57] Luo A F, Jiang X S, Lin H, Yin J. J. Mater. Chem., 2011, 21(34): 12753.
[58] Matsukawa K, Fukuda T, Watase S, Goda H. J. Photopolym. Sci. Technol., 2010, 23(1): 115.
[59] Chen Y Z, Wang K Y, Yang H H, Liu Y X, Yao S Z, Chen B, Nie L H, Xu G M. J. Chromatogr. A, 2012, 1233: 91.
[60] Yang H H, Chen Y Z, Liu Y X, Nie L H, Yao S Z. Electrophoresis, 2013, 34(4): 510.
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