Synthesis of ω-phosphonated poly(ethylene oxide)s through the combination of kabachnik-fields reaction and "click" chemistry

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 51, Issue 2, 2013, Pages 415-423

  N'Guyen, Thi Thanh Thuy ^a   Oussadi, Karima ^a,b   Montembault, Véronique ^a   Fontaine, Laurent ^a  

^a UNIVERSITÉ DU MAINE   (France)

^b UNIVERSITÉ DES SCIENCES ET DE LA TECHNOLOGIE D ORAN MOHAMED BOUDIAF   (Algeria)

Author keywords

"click" chemistry; aminophosphonates; Atherton Todd reaction; functionalization of polymers; Kabachnik Fields reaction; MALDI; modification; poly(ethylene oxide); synthesis; water soluble polymers

Indexed keywords

AMINOPHOSPHONATES; ATHERTON-TODD; CLICK CHEMISTRY; FUNCTIONALIZATION OF POLYMERS; KABACHNIK-FIELDS REACTION; MALDI; MODIFICATION; WATERSOLUBLE POLYMERS;

ACETYLENE; ANIONIC POLYMERIZATION; CYCLOADDITION; ETHERS; ORGANIC ACIDS; POLYETHYLENE OXIDES; POLYMERS;

SYNTHESIS (CHEMICAL);

EID: 84870981434     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26399     Document Type: Article

References (62)

1. David, G.; Negrell-Guirao, C.; Iftene, F.; Boutevin, B.; Chougrani, K., Polym. Chem. 2012, 3, 265-274.
2. Maiti, S.; Banerjee, S.; Palit, S. K., Prog. Polym. Sci. 1993, 18, 227-261.
3. Penczek, S.; Pretula, J.; Kaluzynski, K., Biomacromolecules 2005, 6, 547-551.
4. Oussadi, K.; Montembault, V.; Belbachir, M.; Fontaine, L., J. Appl. Polym. Sci. 2011, 122, 891-897.
5. Lu, S. Y.; Hamerton, I., Prog. Polym. Sci. 2002, 27, 1661-1672.
6. Fontaine, L.; Derouet, D.; Chairatanathavorn, S.; Brosse, J. C., React. Polym. 1993, 19, 47-54.
7. Ménard, L.; Fontaine, L.; Brosse, J. C., React. Polym. 1994, 23, 201-212.
8. Fontaine, L.; Derouet, D.; Chairatanathavorn, S.; Brosse, J. C., Eur. Polym. J. 1995, 31, 109-120.
9. Monge, S.; Canniccioni, B.; Graillot, A.; Robin, J., J. Biomacromolecules 2011, 12, 1973-1982.
10. Wang, Y. C.; Yuan, Y. Y.; Du, J. Z.; Yang, X. Z.; Wang, J., Macromol. Biosci. 2009, 9, 1154-1164.
11. Zhao, Z.; Wang, J.; Mao, H. Q.; Leong, K. W., Adv. Drug Deliv. Rev. 2003, 55, 483-499.
12. Brosse, J. C.; Derouet, D.; Fontaine, L.; Chairatanathavorn, S., Makromol. Chem. 1989, 190, 2339-2345.
13. Brosse, J. C.; Fontaine, L.; Derouet, D.; Chairatanathavorn, S., Makromol. Chem. 1989, 190, 2329-2338.
14. Fontaine, L.; Derouet, D.; Brosse, J. C., Eur. Polym. J. 1990, 26, 857-863.
15. Fontaine, L.; Derouet, D.; Brosse, J. C., Eur. Polym. J. 1990, 26, 865-870.
16. Fontaine, L.; Marbœuf, C.; Brosse, J. C.; Maingault, M.; Dehaut, F., Macromol. Chem. Phys. 1996, 197, 3613-3621.
17. Suzuki, S.; Whittaker, M. R.; Grondahl, L.; Monteiro, M. J.; Wentrup-Byrne, E., Biomacromolecules 2006, 7, 3178-3187.
18. Moszner, N.; Salz, U.; Zimmermann, J., Dent. Mater. 2005, 21, 895-910.
19. Catel, Y.; Degrange, M.; Le Pluart, L.; Madec, P. J.; Pham, T. N.; Chen, F.; Cook, W. D., J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 5258-5271.
20. Catel, Y.; Besse, V.; Zulauf, A.; Marchat, D.; Pfund, E.; Pham, T. N.; Bernache-Assolant, D.; Degrange, M.; Lequeux, T.; Madec, P. J.; Le Pluart, L., Eur. Polym. J. 2012, 48, 318-330.
21. Harris, J. M., Poly(Ethylene Glycol): Chemistry and Biotechnical and Biomedical Applications; Plenum Press: New York, 1972.
22. Oussadi, K.; Montembault, V.; Fontaine, L., J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 5124-5128.
23. Le, D.; Montembault, V.; Soutif, J. C.; Rutnakornpituk, M.; Fontaine, L., Macromolecules 2010, 43, 5611-5617.
24. Zhang, S.; Li, A.; Zou, J.; Lin, L. Y.; Wooley, K. L., ACS Macro. Lett. 2012, 1, 328-333.
25. Thompson, M. S.; Vadala, T. P.; Vadala, M. L.; Lin, Y.; Riffle, J. S., Polymer 2008, 49, 345-373.
26. Li, J.; Kao, W. J., Biomacromolecules 2003, 4, 1055-1067.
27. Mongondry, P.; Bonnans-Plaisance, C.; Jean, M.; Tassin, J. F., Macromol. Rapid Commun. 2003, 24, 681-685.
28. Zeng, F.; Allen, C., Macromolecules 2006, 39, 6391-6398.
29. Parrish, B.; Breitenkamp, B.; Emrik, T., J. Am. Chem. Soc. 2005, 127, 7404-7410.
30. Hiki, S.; Kataoka, K., Bioconjugate Chem. 2010, 21, 248-254.
31. Raynaud, J.; Absalon, C.; Gnanou, Y.; Taton, D., Macromolecules 2010, 43, 2814-2823.
32. Li, Z.; Chau, Y., Bioconjugate Chem. 2011, 22, 518-522.
33. Laurent, S.; Forge, D.; Port, M.; Roch, A.; Robic, C.; Vander Elst, L.; Muller, R. N., Chem. Rev. 2008, 108, 2064-2110.
34. Qi, L.; Seghal, A.; Castaing, J.-C.; Chapel, J.-P.; Fresnais, J.; Berret, J. F.; Cousin, F., ACS Nano 2008, 2, 879-888.
35. Tromsdorf, U. I.; Bruns, O. T.; Salmen, S. C.; Beisiegel, U.; Weller, H., Nano Lett. 2009, 9, 4434-4440.
36. Shephard, J. J.; Dickie, S. A.; McQuillan, A. J., Langmuir 2010, 26, 4048-4056.
37. Liu, X. L.; Fan, H. M.; Yi, J. B.; Yang, Y.; Choo, E. S. G.; Xue, X. M.; Fan, D. D.; Ding, J., J. Mater. Chem. 2012, 22, 8235-8244.
38. Na, H. B.; Lee, I. S.; Seo, H.; Park, Y. I.; Lee, J. H.; Kim, S. W.; Hyeon, T., Chem. Commun. 2007, 5167-5169.
39. Basly, B.; Felder-Flesch, D.; Perriat, P.; Billotey, C.; Taleb, J.; Pourroy, G.; Begin-Colin, S., Chem. Commun. 2010, 46, 985-987.
40. White, M. A.; Johnson, J. A.; Koberstein, J. T.; Turro, N. J., J. Am. Chem. Soc. 2006, 128, 11356-11357.
41. Boyer, C.; Bulmus, V.; Priyanto, P.; Teoh, W. Y.; Amal, R.; Davis, T. P., J. Mater. Chem. 2009, 19, 111-123.
42. Boyer, C.; Priyanto, P.; Davis, T. P.; Pissuwan, D.; Bulmus, V.; Kavallaris, M.; Teoh, W. Y.; Amal, R.; Carol, M.; Woodward, R.; St Pierre, T., J. Mater. Chem. 2010, 20, 255-265.
43. Quéffelec, C.; Petit, M.; Janvier, P.; Knight, D. A.; Bujoli, B., Chem. Rev. 2012, 112, 3777-3807.
44. Essahli, M.; Ganachaud, F.; In, M.; Boutevin, B., J. Appl. Polym. Sci. 2008, 108, 483-490.
45. Traina, C. A.; Schwartz, J., Langmuir 2007, 23, 9158-9161.
46. Goff, J. D.; Huffstetler, P. P.; Miles, W. C.; Pothayee, N.; Reinholz, C. M.; Ball, S.; Davis, R. M.; Riffle, J. S., Chem. Mater. 2009, 21, 4784-4795.
47. Mosquet, M.; Chevalier, Y.; Brunel, S.; Guicquero, J. P.; Le Perchec, P., J. Appl. Polym. Sci. 1997, 65, 2545-2555.
48. Moedritzer, K.; Irani, R. R., J. Org. Chem. 1966, 31, 1603-1607.
49. Atherton, F. R.; Openshaw, H. T.; Todd, A. R., J. Chem. Soc. 1945, 660-663.
50. Kabachnik, M. I.; Medve, T. Y., Dokl. Akad. Nauk. SSSR 1952, 83, 689-692
51. Kabachnik, M. I.; Medve, T. Y., Chem. Abstr. 1953, 47, 2724b.
52. Fields, E. K., J. Am. Chem. Soc. 1952, 74, 1528-1531.
53. Zefirov, N. S.; Matveeva, E. D., Arkivoc 2008, 1-17.
54. Kolb, H. C.; Finn, M. G.; Sharpless, K. B., Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
55. Zwierzak, A., Synthesis 1982, 11, 920-922.
56. McKenna, C. E.; Higa, M. T.; Cheung, N. H.; McKenna, M. C., Tetrahedron Lett. 1977, 18, 155-158.
57. Kishore Kumar, G. D.; Saenz, D.; Lokesh, G. L.; Natarajan, A., Tetrahedron Lett. 2006, 47, 6281-6284.
58. Beers, S. A.; Schwender, C. F.; Loughney, D. A.; Malloy, E.; Demarest, K.; Jordan, J., Bioorg. Med. Chem. 1996, 4, 1693-1701.
59. Metcalf, B.; Casara, P., Tetrahedron Lett. 1975, 16, 3337-3340.
60. Kraicheva, I.; Bogomilova, A.; Tsacheva, I.; Momekov, G.; Troev, K., Eur. J. Med. Chem. 2009, 44, 3363-3367.
61. Maier, L.; Diel, P. J., Phosphorus Sulfur Silicon Relat. Elem. 1991, 57, 57-64.
62. Cottier, L.; Descotes, G.; Lewkowski, J.; Skowronski, R., Phosphorus Sulfur Silicon Relat. Elem. 1996, 116, 93-100.