Efficient Cu(I) acetate-catalyzed cycloaddition of multifunctional alkynes and azides: From solution to bulk polymerization

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 52, Issue 2, 2014, Pages 239-247

  Sandmann, Benedict ^a   Happ, Bobby ^a,b   Hager, Martin D ^a   Vitz, Jürgen ^a,b   Rettler, Erik ^a   Burtscher, Peter ^c   Moszner, Norbert ^c   Schubert, Ulrich S ^a,b  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b DUTCH POLYMER INSTITUTE DPI   (Netherlands)

^c IVOCLAR VIVADENT AG   (Liechtenstein)

Author keywords

bulk polymerization; catalyst screening; click chemistry; crosslinking; cycloaddition; differential scanning calorimetry (DSC); kinetics; nanoindentation; step growth polymerization

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; BULK POLYMERIZATION; CATALYST SCREENING; CLICK CHEMISTRY; DEPTH SENSING INDENTATION; MODIFICATION OF POLYMERS; POLYMERIZATION KINETICS; STEP-GROWTH POLYMERIZATIONS;

BENZENE; BENZENE REFINING; CATALYSIS; COPPER; CROSSLINKING; CYCLOADDITION; DIFFERENTIAL SCANNING CALORIMETRY; ENZYME KINETICS; GROWTH KINETICS; HYDROCARBONS; KINETICS; MECHANICAL PROPERTIES; NANOINDENTATION; NITROGEN COMPOUNDS; POLYMERS; REACTION KINETICS; SYNTHESIS (CHEMICAL); VOLATILE FATTY ACIDS;

POLYMERIZATION;

EID: 84890115163     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26996     Document Type: Article

References (41)

1. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
2. C. W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
3. M. A. Tasdelen, Polym. Chem.-UK 2011, 2, 2133-2145.
4. A. B. Lowe, Polym. Chem.-UK 2010, 1, 17-36.
5. M. Meldal, Macromol. Rapid Commun. 2008, 29, 1016-1051.
6. C. R. Becer, R. Hoogenboom, U. S. Schubert, Angew. Chem. Int. Ed. 2009, 48, 4900-4908.
7. F. Kloss, U. Kohn, B. O. Jahn, M. D. Hager, H. Goerls, U. S. Schubert, Chem. Asian J. 2011, 6, 2816-2824.
8. K. Kempe, R. Hoogenboom, M. Jaeger, U. S. Schubert, Macromolecules 2011, 44, 6424-6432.
9. A. R. Katritzky, N. K. Meher, S. Hanci, R. Gyanda, S. R. Tala, S. Mathai, R. S. Duran, S. Bernard, F. Sabri, S. K. Singh, J. Doskocz, D. A. Ciaramitaro, J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 238-256.
10. U. Mansfeld, C. Pietsch, R. Hoogenboom, C. R. Becer, U. S. Schubert, Polym. Chem. 2010, 1, 1560-1598.
11. K. Kempe, A. Krieg, C. R. Becer, U. S. Schubert, Chem. Soc. Rev. 2012, 41, 176-191.
12. M. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952-3015.
13. H. Nandivada, X. Jiang, J. Lahann, Adv. Mater. 2007, 19, 2197-2208.
14. J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249-1262.
15. W. H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 2007, 28, 15-54.
16. W. H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 2008, 29, 952-981.
17. H. Struthers, T. L. Mindt, R. Schibli, Dalton Trans. 2010, 39, 675-696.
18. P. L. Golas, K. Matyjaszewski, Chem. Soc. Rev. 2010, 39, 1338-1354.
19. J. A. Opsteen, J. C. M. van Hest, J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 2913-2924.
20. H. Gao, K. Matyjaszewski, Macromolecules 2006, 39, 4960-4965.
21. H. Durmaz, A. Dag, E. Erdogan, A. L. Demirel, G. Hizal, U. Tunca, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 99-108.
22. D. Wu, X. Song, T. Tang, H. Zhao, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 443-453.
23. J. Yin, Z. Ge, H. Liu, S. Liu, J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 2608-2619.
24. J. L. Mynar, T.-L. Choi, M. Yoshida, V. Kim, C. J. Hawker, J. M. J. Frechet, Chem. Commun. 2005, 5169-5171.
25. P. Wu, M. Malkoch, J. N. Hunt, R. Vestberg, E. Kaltgrad, M. G. Finn, V. V. Fokin, K. B. Sharpless, C. J. Hawker, Chem. Commun. 2005, 5775-5777.
26. C. Ornelas, J. Ruiz Aranzaes, E. Cloutet, S. Alves, D. Astruc, Angew. Chem. Int. Ed. 2007, 46, 872-877.
27. S. Binauld, D. Damiron, T. Hamaide, J. P. Pascault, E. Fleury, E. Drockenmuller, Chem. Commun. 2008, 4138-4140.
28. B. Sandmann, B. Happ, J. Vitz, M. D. Hager, P. Burtscher, N. Moszner, U. S. Schubert, Polym. Chem.-UK 2013, 4, 3938-3942.
29. M. Gragert, M. Schunack, W. H. Binder, Macromol. Rapid Commun. 2011, 32, 419-425.
30. M. Schunack, M. Gragert, D. Dohler, P. Michael, W. H. Binder, Macromol. Chem. Phys. 2012, 213, 205-214.
31. X. Sheng, T. C. Mauldin, M. R. Kessler, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 4093-4102.
32. F. Himo, T. Lovell, R. Hilgraf, V. V. Rostovtsev, L. Noodleman, K. B. Sharpless, V. V. Fokin, J. Am. Chem. Soc. 2005, 127, 210-216.
33. S. Binauld, F. Boisson, T. Hamaide, J. P. Pascault, E. Drockenmuller, E. Fleury, J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 5506-5517.
34. D. Wang, N. Li, M. M. Zhao, W. L. Shi, C. W. Ma, B. H. Chen, Green Chem. 2010, 12, 2120-2123.
35. S. Lal, S. Diez-Gonzalez, J. Org. Chem. 2011, 76, 2367-2373.
36. X. Sheng, D. M. Rock, T. C. Mauldin, M. R. Kessler, Polymer 2011, 52, 4435-4441.
37. J. Rey, F. C. García, J. M. García, React. Funct. Polym. 2011, 71, 948-957.
38. P. S. Donnelly, S. D. Zanatta, S. C. Zammit, J. M. White, S. J. Williams, Chem. Commun. 2008, 2459-2461.
39. S. T. Abu-Orabi, R. E. Harmon, J. Chem. Eng. Data 1986, 31, 379-380.
40. E. F. J. Rettler, J. M. Kranenburg, H. M. L. Lambermont-Thijs, R. Hoogenboom, U. S. Schubert, Macromol. Chem. Phys. 2010, 211, 2443-2448.
41. W. C. Oliver, G. M. Pharr, J. Mater. Res. 1992, 7, 1564-1583.