OALib Journal期刊
ISSN: 2333-9721
费用:99美元
巯基-烯点击化学
, PP. 385-394
Keywords: 点击化学 ,巯基-烯反应 ,功能聚合物 ,拓扑结构 ,表面修饰 ,生物分子
Abstract:
点击化学自2001年由Sharpless提出后,由于其高效、可靠、高选择性的特点迅速成为药物和高分子材料合成的新方法。随着对点击化学研究的深入,其反应类型在不断增多,应用范围也在不断扩大。自由基或亲核试剂引发的巯基-烯反应作为其中一种新型的点击反应具有点击化学的所有特性。本文从点击化学的概念、特征和类型出发,重点介绍了巯基-烯反应的机理和在合成功能聚合物、制备拓扑结构高分子、表面修饰以及生物药物等方面的应用,并对巯基-烯反应的最新研究成果进行综述,最后展望了巯基-烯的点击化学的发展前景。
References
[1] Lee T Y, Roper T M, Jonsson E S, Guymon C A, Hoyle C E. Macromolecules, 2004, 37: 3659-3665
[2] 郭圣荣(Guo S R). 药用高分子材料(Polymeric Medical Materials). 北京: 人民卫生出版社(Beijing: People's Medical Publishing House), 2009. 265-289
[3] Bajpai A K, Shukla S K, Bhanu S, Kankane S. Prog. Polym. Sci., 2008, 33: 1088-1118
[4] Zhang K, Lackey M A, Cui J, Tew G N. J. Am. Chem. Soc., 2011, 133: 4140-4148
[5] Connal L A, Kinnane C R, Zelikin A N, Caruso F. Chem. Mater., 2009, 21, 576-578
[6] Xiong X Q. Aust. J. Chem., 2009, 62: 1371-1377
[7] Chen B, Jerger K, Frechet J M J, Szoka F C. J. Control. Release, 2009, 140: 203-209
[8] Hennink W, Park K. J. Control. Release, 2009, 140: 185-185
[9] Misaka H, Kakuchi R, Zhang C H, Sakai R, Satoh T, Kakuchi T. Macromolecules, 2009, 42: 5091-5096
[10] Massignani M, LoPresti C, Blanazs A, Madsen J, Armes S P, Lewis A L, Battaglia G. Small, 2009, 5: 2424-2432
[11] Adronov Frechet J M J. Chem. Commum., 2000, 1701-1710
[12] Lee C C, Yoshida M, Frechet J M J, Dy E E, Szoka F C. Bioconjugate Chem., 2005, 16: 535-541
[13] Fu Y Q, Li Y, Li J, Yan S, Bo Z S. Macromolecules, 2004, 37: 6395-6400
[14] Tomalia D A, Baker H, Dewald J, Hall M, Kallo G, Martin S, Ryder J, Smith P. Polym J., 1985, 17: 117-132
[15] Ashton P R, Boyd S E, Brown C L, Jayaraman N, Stoddart J F. Angew. Chem. Int. Ed., 1997, 36: 732-735
[16] Hawker C J, Frechet J M J. J. Am. Chem. Soc., 1990, 112: 7638-7647
[17] Onitsuka K, Fujimoto M, Ohshiro N, Takahashi S. Angew. Chem. Int. Ed., 1999, 38: 689-692
[18] Killops K L, Campos L M, Hawker C J. J. Am. Chem. Soc., 2008, 130: 5062-5064
[19] Ueda J, Kamigaito M, Sawamoto M. Macromolecules, 1998, 31: 6762-6768
[20] Zhang T, Wu Y P, Pan X M, Zheng Z H, Ding X B, Peng Y X. Eur. Polym. J., 2009, 45: 1625-1633
[21] Bexell U, Berger R, Olsson M, Grehk T M, Sundell P E, Johansson M.Thin Solid Films, 2006, 515: 838-841
[22] Bexell U, Olsson M, Sundell P E, Johansson M, Carlsson P, Hellsing A. Appl. Surf. Sci., 2004, 231: 362-365
[23] Khire V S, Kloxin A, Clouch C L, Anseth K S, Bowman C N. J. Polym. Sci. Part A, 2008, 46: 6896-6906
[24] Pogantsch A, Rentenberger S, Langer G., Keplinger J, Kern W, Zojer E. Adv. Funct. Mater., 2005, 15: 403-409
[25] Crowe J A, Genzer J. J. Am. Chem. Soc., 2005, 127: 17610-17611
[26] Gress A,Volkel A, Schlaad H. Macromolecules, 2007, 40: 7928-7933
[27] Wittrock S, Becker T, Kunz H, Angew. Chem. Int. Ed., 2007, 46: 5226-5230
[28] Jacquelyn A C, Lu H, Jeffrey W S, Christopher N B. Dental Materials, 2005, 21: 1137-1143
[29] Chan J W, Hoyle C E, Lowe A B. J. Am. Chem. Soc., 2009, 131: 5751-5753
[30] Jonkheijm P, Weinrich D, Kohn M, Engelkamp H, Christianen P C M, Kuhlmann J, Mann J C, Nusse D, Schroeder H, Wacker R, Breinbauer R, Niemeyer C M, Waldmann H. Angew. Chem. Int. Ed., 2008, 47: 4421-4424
[31] Li G L, Xu L Q, Neoh K G, Kang E T. Macromolecules, 2011, 44: 2365-2370
[32] Fiore M, Marra A, Dondoni A. J. Org. Chem., 2009, 74: 4422-4425
[33] Kolb H C, Finn M G, Sharpless K B. Angew. Chem. Int. Ed., 2001, 40: 2004-2021
[34] Kolb H C, Sharpless K B. Drug Discovery Today, 2003, 8: 1128-1137
[35] 邱素艳(Qiu S Y),高森(Gao S),林振宇(Lin Z Y),陈国南(Zhen G N). 化学进展(Progress in Chemistry),2011, 23: 637-648
[36] 董卫莉(Dong W L),赵卫光(ZhaoW G),李玉新(Li Y X). 有机化学 (Chinese Journal of Organic Chemistry),2006, 26: 271-277
[37] Meldal M, Tornoe C W. Chem. Rev., 2008, 108: 2952-3015
[38] Finn M G, Kolb H C, Fokin V V,Sharpless K B. 化学进展(Prog. Chem.), 2008, 20: 1-3
[39] Sumerlin B S, Vogt A P. Macromolecules, 2010, 43: 1-13
[40] Hoogenboom R. Angew. Chem. Int. Ed., 2010, 49: 2-5
[41] Lowe A B, Hoyle C E, Bowman C N. J. Mater. Chem., 2010, 20: 4745-4750
[42] Garg S M, Xiong X B, Lu C H, Lavasanifar A. Macromolecules, 2011, 44: 2058-2066
[43] Wang Q, Chan T R, Hilgraf R, Fokin V V, Sharpless K B, Finn M G. J. Am. Chem. Soc., 2003, 125: 3192-3193
[44] Gierlich J, Burley G A, Gramlich P M E, Hammond D M, Carell T. Org. Lett., 2006, 8: 3639-3642
[45] Qin A J, Tang L, Lam J W Y. Adv. Funct. Mater., 2009, 19: 1891-1900
[46] Ates Z, Thornton P D, Heise A. Polym. Chem., 2011, 2: 309-312
[47] Lundberg P, Walter M V, Montanez M I, Hult D, Hult A, Nystromc A, Malkoch M. Polym. Chem., 2011, 2: 394-402
[48] Bernhardt C, Stoffelbach F, Charleux B. Polym. Chem., 2011, 2: 229-235
[49] Kade M J, Burke D J, Hawker C J. J. Polym. Sci. Part A: Polym. Chem., 2010, 48: 743-750
[50] Cramer N B, Reddy S K, Lu H, Cross T, Raj R, Bowman C N. J. Polym Sci. Part A: Poly. Chem., 2004, 42: 1752-1757
[51] Cramer N B, Reddy S K, Cole M, Hoyle C, Bowman C N. J. Polym. Sci. Part A: Poly. Chem., 2004, 42: 5817-5826
[52] Hensarling R M, Doughty V A, Chan J W, Patton D L. J. Am. Chem. Soc., 2009, 131: 14673-14675
[53] Shin J, Matsushima H, Comer C M, Bowman C N, Hoyle C E. Chem. Mater., 2010, 22: 2616-2625
[54] Clark T, Hoyle C, Nazarenko S. J. Coat Technol. Res., 2008, 5: 345-351
[55] Khire V S, Lee T Y, Bowman C N. Macromolecules, 2007, 40: 5669-5677
[56] Gu W F, Chen G J, Stenzel M H. J. Polym. Sci. Part A: Polym. Chem., 2009, 47: 5550-5556
[57] Nilsson C, Malmstrom E, Johansson M, Trey S M. J. Polym. Sci. Part A : Polym. Chem., 2009, 47: 589-601
[58] Shin J, Nazarenko S, Hoyle C E. Macromolecules, 2009, 42: 6549-6557
[59] Becer C R, Hoogenboom R, Schubert U S. Angew. Chem. Int. Ed., 2009, 48: 4900-4908
[60] Mazzolini J, Boyron O, Monteil V, Gigmes D, Bertin D, Agosto F D, Boisson C. Macromolecules, 2011, 44: 3381-3387
[61] Li Y W, Zhang W B, Janoski J E, Li X P, Dong X H, Wesdemiotis C, Quirk R P, Cheng S Z D. Macromolecules, 2011, 44: 3328-3337
[62] Tempelaar S, Mespouille L, Dubois P, Dove A P. Macromolecules, 2011, 44: 2084-2091
[63] Reddy S K, Cramer N B, Cross T, Bowman C N. J. Chem. Mater., 2003, 15: 4257-4261
[64] Huynh V T, Chen G J, Souza P, Stenzel M H. Biomacromolecules, 2011, 12: 1738-1751
[65] Chen G, Amajjahe S, Stenzel M H. Chem. Commun., 2009, 1198-1120
[66] Pan H Z, Yang J Y, kova P K, Kopecek J. Biomacromolecules, 2011, 12: 247-252
[67] Cakmakc E, Mulazim Y, Kahraman M V, ApohanN K. React. Funct. Polym., 2011, 71: 36-41
[68] Zhang S Y, Zhao Y. ACS Nano, 2011, 5: 2637-2646
[69] Desroches M, Caillol S, Lapinte V, Auvergne R, Boutevin B. Macromolecules, 2011, 44: 2489-2500
[70] 李娟(Li J),段明(Duan M),张烈辉(ZhangL H),蒋晓慧(Jiang X H). 化学进展(Progress in Chemistry),2007, 19: 1754-1760
[71] 张涛(Zhang T),郑朝晖(Zheng Z H),成煦(Cheng X),丁小斌(Ding X B),彭宇行(Peng Y X). 化学进展(Progress in Chemistry), 2008, 20: 1090-1101
[72] Moses J, Moorhouse A. Chem. Soc. Rev., 2007, 36: 1249-1262
[73] Han T, Chen C F. J. Org. Chem., 2008, 73: 7735-7742
[74] Binder W H, Sachsenhofer R. Macromol. Rapid Commum., 2007, 28: 15-54
[75] Zhang K, Lackey M A, Wu Y, Tew G N. J. Am. Chem. Soc., 2011, 133: 6906-6909
[76] Luo K, Yang J Y, Kopeckova P, Kopecek J R. Macromolecules, 2011, 44: 2481-2488
[77] Agard N J, Prescher J A, Bertozzi C R A. J. Am. Chem. Soc., 2004, 126: 15046-15047
[78] Lutz J F. Angew. Chem. Int. Ed., 2008, 47: 2182-2184
[79] Lallana E, Fernandez M E, Riguera, R. J. Am. Chem. Soc., 2009, 131: 5748-5750
[80] Jim C K W, Qin A, Lam J W Y. Adv. Funct. Mater., 2010, 20: 1319-1328
[81] Rutledge R D, Warner C L, Pittman J W, Addleman R S, Engelhard M, Chouyyok W, Warner M G. Langmuir, 2010, 26: 12285-12292
[82] Lutz J F, Schlaad H. Polymer, 2008, 49: 817-824
[83] Li G L, Xu L Q, Tang X Z, Neoh K G, Kang E T. Macromolecules, 2010, 43: 5797-5803
[84] Rutherglen B G, McBath R A, Huang Y L, Shipp D A. Macromolecules, 2010, 43: 10297-10303
[85] Lowe A B. Polym. Chem., 2010, 1: 17-36
[86] Hoyle C E, Bowman C N. Angew. Chem. Int. Ed., 2010, 49: 1540-1573
[87] Holy C E, Tai Y L, Roper T M. J. Polym. Sci. Part A: Poly. Chem., 2004, 42: 5301-5338
[88] Reddy S K, Cramer N B, Brien A K O, Cross T, Raj R, Bowman C N. Macromolecular, 2004, 206: 361-374
[89] 宋家乐(Song J L),陈立新(Chen L X),陈伟伟(Chen W W),景晨丽(Jing C L),王汝敏(Wang N M). 化学通报(Chemical Communications), 2006, 69: 1-6
[90] Chan J W, Shin J, Hoyle C E, Bowman C N, Lowe A B. Macromolecules, 2010, 43: 4937-4942
[91] Chen G J, Kumar J, Gregory A, Stenzel M H. Chem. Commun., 2009, 6291-6293
[92] Konkolewicz D, Gray W A, Perrier S. J. Am. Chem. Soc., 2009, 131: 18075-18077
[93] Dondoni A. Angew. Chem. Int. Ed., 2008, 47: 8995-8997
[94] Nuttelman C R, Rice M A, Rydholm A E, Salinas C N, Shah D N, Anseth K S. Prog. Polym. Sci., 2008, 33: 167-179
[95] Campos L M, Killops K L, Sakai R, Paulusse J M J, Damiron D, Drockenmuller E, Messmore B W, Hawker C J. Macromolecules, 2008, 4: 7063-7070
[96] Pounder R J, Stanford M J, Brooks P, Richards S P, Dove A P. Chem. Commun., 2008, 5158-5160
[97] Stanford M J, Dove A P. Macromolecules, 2009, 42: 141-147
[98] Morgan C R, Ketley A D. J. Polym. Sci. Polym. Lett. Ed., 1978, 16: 75-79
[99] Morgan C R, Magnotta F, Ketley A D. J. Polym. Sci. Polym. Chem. Ed., 1977, 15: 627-645
[100] Dohi K, Tsuchiya Y, Endo K, Masumoto A, Kawasaki H, Arakawa R. Macromolecules, 2011, 44: 1808-1813
[101] Campos L M, Meinel I, Guino R G, Schierhorn M, Gupta N, Stucky G D, Hawker C J. Adv. Mater., 2008, 20: 3728-3733
[102] Truong T A, Campos L M, Matioli E, Meinel I, Hawker C J, Weisbuch C, Petroff P M. Appl. Phys. Lett., 2009, 94: 920-925
[103] Xiong X Q, Xu Y H. Polym. Bull., 2010, 65: 455-463
[104] 熊兴泉(Xiong X Q). 有机化学 (Chinese Journal of Organic Chemistry), 2010, 30: 307-310
[105] Oike H, Washizuka M, Tezuka Y. Macromol. Rapid Commum., 2001, 22: 1128-1134
[106] Endo K. Adv. Polym. Sci., 2008, 217: 121-183
[107] Nasongkla N, Chen B, Macaraeg N, Fox M E, Frechet J M J, Szoka F C. J. Am. Chem. Soc., 2009, 131: 3842-3843
[108] Montanez M I, Campos L M, Antoni P, Hed Y, Walter M V, Krull B T, Khan A, Hult A, Harker C J, Malkoch M. Macromolecules, 2010, 43: 6004-6013
[109] Ma X P, Tang J B, Shen Y, Fan M, Tang H, Radosz M. J. Am. Chem. Soc., 2009, 131: 14795-14803
[110] Coessens V, Pintauer T, Matyjaszewski K. Prog. Polym. Sci., 2001, 26: 337-377
[111] Chan J W, Yu B, Hoyle C E, Lowe A B. Chem. Commun., 2008, 4959-4961
[112] Chan J W, Yu B, Hoyle C E, Lowe A B. Polymer, 2009, 50: 3158-3168
[113] Xu J T, Tao L, Boyer C, Lowe A B, Davis T P. Macromolecules, 2010, 43: 20-24
[114] Degirmenci M, Genli N. Macromol. Chem. Phys., 2009, 210: 1617-1623
[115] Semsarilar M, Ladmiral V, Perrier S. Macromolecules, 2010, 43: 1438-1443
[116] Koh M L, Konkolewicz D, Perrier S. Macromolecules, 2011, 44: 2715-2724
[117] Dennis G R, Garnett J L, Zilic E. Radiat. Phys. Chem., 2004, 71: 217-221
[118] Crowe J A, Efimenko K, Genzer J, Schwark D W. Responsive Polymer Materials (Ed. Minko S), Amesterdam: Wiley-Black-Well, 2006. 184-195
[119] Slaney A M, Wright V A, Meloncelli P J, Harris K D, West L J, Lowary T L, Buriak J M. Appl. Mater. Interfaces, 2011, 3: 1601-1612
[120] Brummelhuis N T, Diehl C, Schlaad H. Macromolecules, 2008, 41: 9946-9947
[121] Triola G, Brunsveld L, Waldmann H. J. Org. Chem., 2008, 73: 3646-3649
[122] Xu H, Baidoo K E, Wong K J, Brechbiel M W. Bioorg. Med. Chem. Lett., 2008, 18: 2679-2683
[123] Wong L J, Kavallaris M, Bulmus V. Polym. Chem., 2011, 2: 385-393
Full-Text
Contact Us
service@oalib.com
QQ:3279437679
WhatsApp +8615387084133