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R. Riva, Stéphanie Schmeits, F. Stoffelbach, C. Jérôme, R. Jerome, P. Lecomte (2005)
Combination of ring-opening polymerization and "click" chemistry towards functionalization of aliphatic polyesters.Chemical communications, 42
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Dirk Steenis, O. David, G. Strijdonck, J. Maarseveen, J. Reek (2005)
Click-chemistry as an efficient synthetic tool for the preparation of novel conjugated polymers.Chemical communications, 34
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Jean‐François Lutz, H. Börner, Katja Weichenhan (2005)
Combining Atom Transfer Radical Polymerization and Click Chemistry: A Versatile Method for the Preparation of End‐Functional PolymersMacromolecular Rapid Communications, 26
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R. O’Reilly, Maisie Joralemon, C. Hawker, K. Wooley (2006)
Fluorogenic 1,3-dipolar cycloaddition within the hydrophobic core of a shell cross-linked nanoparticle.Chemistry, 12 26
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(2006)
For a theoretical treatment -
Tae‐Dong Kim, Jingdong Luo, Yanqing Tian, Jae-Won Ka, N. Tucker, M. Haller, Jaewook Kang, A. Jen (2006)
Diels−Alder “Click Chemistry” for Highly Efficient Electrooptic PolymersMacromolecules, 39
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R. Shintani, G. Fu (2003)
A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles.Journal of the American Chemical Society, 125 36
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B. Sumerlin, N. Tsarevsky, G. Louche, R. Lee, K. Matyjaszewski (2005)
Highly Efficient “Click” Functionalization of Poly(3-azidopropyl methacrylate) Prepared by ATRPMacromolecules, 38
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A. Dirks, S. Berkel, N. Hatzakis, J. Opsteen, F. Delft, J. Cornelissen, A. Rowan, J. Hest, F. Rutjes, R. Nolte (2005)
Preparation of biohybrid amphiphiles via the copper catalysed Huisgen [3 + 2] dipolar cycloaddition reaction.Chemical communications, 33
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B. Gacal, H. Durmaz, M. Taşdelen, G. Hizal, Umit Tunca, Y. Yagcı, A. Demirel (2006)
Anthracene−Maleimide-Based Diels−Alder “Click Chemistry” as a Novel Route to Graft CopolymersMacromolecules, 39
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H. Orgueira, Demosthenes Fokas, Y. Isome, P. Chan, C. Baldino (2005)
Regioselective synthesis of [1,2,3]-triazoles catalyzed by Cu(I) generated in situ from Cu(0) nanosize activated powder and amine hydrochloride saltsTetrahedron Letters, 46
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Jun-Cai Meng, Claudia Averbuj, W. Lewis, G. Siuzdak, M. Finn (2004)
Cleavable linkers for porous silicon-based mass spectrometry.Angewandte Chemie, 43 10
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Jennifer Brennan, N. Hatzakis, T. Tshikhudo, N. Dirvianskytė, V. Razumas, S. Patkar, J. Vind, A. Svendsen, R. Nolte, A. Rowan, M. Brust (2006)
Bionanoconjugation via click chemistry: The creation of functional hybrids of lipases and gold nanoparticles.Bioconjugate chemistry, 17 6
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Z. Demko, K. Sharpless (2002)
A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: synthesis of 5-acyltetrazoles from azides and acyl cyanides.Angewandte Chemie, 41 12
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W. Binder, Christian Kluger (2004)
Combining Ring-Opening Metathesis Polymerization (ROMP) with Sharpless-Type “Click” Reactions: An Easy Method for the Preparation of Side Chain Functionalized Poly(oxynorbornenes)Macromolecules, 37
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A. Speers, B. Cravatt (2004)
Profiling enzyme activities in vivo using click chemistry methods.Chemistry & biology, 11 4
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F. Himo, Z. Demko, Louis Noodleman, K. Sharpless (2002)
Mechanisms of tetrazole formation by addition of azide to nitriles.Journal of the American Chemical Society, 124 41
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M. Malkoch, K. Schleicher, É. Drockenmuller, C. Hawker, T. Russell, Peng Wu, V. Fokin (2005)
Structurally diverse dendritic libraries : A highly efficient functionalization approach using Click chemistryMacromolecules, 38
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Z. Demko, K. Sharpless (2002)
A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: synthesis of 5-sulfonyl tetrazoles from azides and sulfonyl cyanides.Angewandte Chemie, 41 12
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H. Kolb, M. Finn, K. Sharpless (2001)
Click Chemistry: Diverse Chemical Function from a Few Good Reactions.Angewandte Chemie, 40 11
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(2001)
, 57 , 9225 ; [ 21 b ] C . O . Kappe For previous examples of copper acetylides in cycloaddition reactions see : [ 26 a ] M . Kinugasa , S . Hashimoto -
J. Gierlich, G. Burley, P. Gramlich, David Hammond, T. Carell (2006)
Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA.Organic letters, 8 17
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S. Bakbak, Peter Leech, B. Carson, Shubham Saxena, W. King, U. Bunz (2006)
1,3-Dipolar Cycloaddition for the Generation of Nanostructured Semiconductors by Heated Probe TipsMacromolecules, 39
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D. Yeo, R. Srinivasan, Grace Chen, S. Yao (2004)
Expanded utility of the native chemical ligation reaction.Chemistry, 10 19
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Chunmei Wei, Chao‐Jun Li (2002)
Enantioselective direct-addition of terminal alkynes to imines catalyzed by copper(I)pybox complex in water and in toluene.Journal of the American Chemical Society, 124 20
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Hartmuth Kolb, K. Sharpless, The Scripps (2003)
The growing impact of click chemistry on drug discovery.Drug discovery today, 8 24
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Junxin Li, H. Grennberg (2006)
Microwave-assisted covalent sidewall functionalization of multiwalled carbon nanotubes.Chemistry, 12 14
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L. Pachón, J. Maarseveen, G. Rothenberg (2005)
Click Chemistry: Copper Clusters Catalyse the Cycloaddition of Azides with Terminal AlkynesAdvanced Synthesis & Catalysis, 347
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A. Link, Mandy Vink, D. Tirrell (2004)
Presentation and detection of azide functionality in bacterial cell surface proteins.Journal of the American Chemical Society, 126 34
- Publisher
- Wiley
- Copyright
- Copyright © 2007 Wiley Subscription Services
- ISSN
- 1022-1336
- eISSN
- 1521-3927
- DOI
- 10.1002/marc.200600625
- Publisher site
- See Article on Publisher Site
Abstract
The modification of polymers after the successful achievement of a polymerization process represents an important task in macromolecular science. Cycloaddition reactions, among them the metal catalyzed azide/alkyne ‘click’ reaction (a variation of the Huisgen 1,3‐dipolar cycloaddition reaction between terminal acetylenes and azides) represents an important contribution towards this endeavor. They combine high efficiency (usually above 95%) with a high tolerance of functional groups and solvents, as well as moderate reaction temperatures (25–70 °C). The present review assembles recent literature for applications of this reaction in the field of polymer science (linear polymers, dendrimers, gels) as well as the use of this and related reactions for surface modification on carbon nanotubes, fullerenes, and on solid substrates, and includes the authors own publications in this field. A number of references (>100) are included.
Journal
Macromolecular Rapid Communications – Wiley
Published: Jan 5, 2007
Keywords: ; ; ; ; ;