One-pot synthesis of a novel water-soluble fullerene-core starlike macromolecule via successive Michael and nucleophilic addition reaction

Chemistry of Materials

Volumn 16, Issue 12, 2004, Pages 2442-2448

  Goswami, Thako Hari ^a   Singh, Rachana ^a   Alam, Sarfaraz ^a   Mathur, Gyanesh N ^a  

^a DEFENCE MATERIALS AND STORES RESEARCH AND DEVELOPMENT ESTABLISHMENT   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MACROMOLECULES; OPTICAL PROPERTIES; REACTION KINETICS; THERMOGRAVIMETRIC ANALYSIS; ULTRAVIOLET RADIATION; UNSATURATED COMPOUNDS;

ACID-CATALYZED REACTION; NUCLEOPHILIC ADDITION REACTION; THERMAL BEHAVIOR;

SYNTHESIS (CHEMICAL);

FULLERENE;

ADDITION REACTION; ARTICLE; CATALYST; CHEMICAL REACTION; FOURIER TRANSFORMATION; INFRARED SPECTROSCOPY; MACROMOLECULE; MICHAEL ADDITION; SYNTHESIS; THERMAL ANALYSIS; THERMOGRAVIMETRY;

EID: 2942525765     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm0350232     Document Type: Article

References (52)

1. Haddon, R. C. Acc. Chem. Res. 1992, 25, 127.
2. Allemand, P. M.; Khemani, K. C.; Koch, A.; Wuld, F.; Holczer, K.; Donovan, S.; Gruner, G.; Thompson, J. D. Science 1991, 253, 301.
3. Jensen, A. W.; Wilson, S. R.; Schuster, D. I. Bioorg. Med. Chem. 1996, 4, 767.
4. Withers, J. C.; Loutfy, R. O.; Lowe, T. P. Fullerene Sci. Technol. 1997, 5, 1.
5. Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537,
6. Prato, M. J. Mater. Chem. 1997, 7, 1097.
7. Smalley, R. E.; Yakobson, B. I. Solid State Commun. 1998, 107, 597.
8. Coq, B.; Planeix, J. M.; Brotons, V. Appl. Catal. A 1998, 173, 175.
9. Diederich, F.; Gomez-Lopez, M. Chem. Soc. Rev. 1999, 28, 263.
10. Da Ros, T.; Prato, M. Chem. Commun. 1999, 663.
11. Hawker, C. J. Macromolecules 1994, 27, 4836.
12. Dai, L. J. Macromol. Sci., Rev. Macromol. Chem. Phys. 1999, 39, 273.
13. Li, F. Y.; Li, Y. L.; Guo, Z. X.; Mo, Y. M.; Fan, L. Z.; Bai, F. L.; Zhu, D. B. Solid State Commun. 1998, 107, 189.
14. Pasimeni, L.; Franco, L.; Ruzzi, M.; Mucci, A.; Schenetti, L.; Luo, C.; Guldi, D. M.; Kordatos, K.; Prato, M. J. Mater. Chem. 2001, 11, 981.
15. Hirsch, A. Adv. Mater. 1993, 5, 859.
16. Chen, Y.; Huang, W. S.; Huang, Z. E.; Cai, R. F.; Chen, S. M.; Yan, X. M. Eur. Polym. J. 1997, 33, 823.
17. Yu, B. C.; Chen, Y.; Cai, R. F.; Huang, Z. E.; Xiao, Y. W. Eur. Polym. J. 1997, 33, 1049.
18. Samulski, E. T.; DeSimone, J. M.; Hunt, M. O., Jr.; Menceloglu, Y. Z.; Jarnagin, R. C.; York, G. A.; Labat, K. B.; Wang, H. Chem. Mater. 1992, 4, 1152.
19. Wignall, G. D.; Affholter, K. A.; Bunick, G. J.; Hunt, M. O., Jr.; Menceloglu, Y. Z.; DeSimone, J. M.; Samulski, E. T. Macromolecules 1995, 28, 6000.
20. Stewart, D.; Imrei C. T. Chem. Commun. 1996, 1383.
21. Cao, T.; Webber, S. E. Macromolecules 1995, 28, 3741.
22. Bunker, C. E.; Lawson, G. E.; Sun, Y. P. Macromolecules 1995, 28, 3744.
23. Camp, A. G.; Lary, A.; Ford, W. T. Macromolecules 1995, 28, 7959.
24. Wang, L. Y.; Ananthraj, V.; Ashok, K.; Chiang, L. Y. Synth. Met. 1999, 103, 2350.
25. He, J. D.; Hang, J.; Li, S. D.; Cheung, M. K. J. Appl. Polym. Sci. 2001, 81, 1286.
26. Hawker, C. J.; Wooley, K. L.; Frechet, J. M. J. Chem. Commun. 1994, 925.
27. Wooley, K. L.; Hawker, C. J.; Frechet, J. M. J.; Wudl, F.; Srdanov, G.; Shi, S.; Li, C.; Kao, M. J. Am. Chem. Soc. 1993, 115, 9836.
28. KawaguchiIkeda, A. M.; Shinkai, S. J. Chem. Soc., Perkin. Trans. 1998, 1, 179.
29. Prato, M.; Maggini, M. Acc. Chem. Res. 1998, 31, 519.
30. Hirsch, A.; Nuber, B. Acc. Chem. Res. 1999, 32, 795.
31. Diederich, F.; Kessinger, R. Acc. Chem. Res. 1999, 32, 537.
32. Echegoyen, L.; Echegoyen, L. E. Acc. Chem. Res. 1998, 31, 593.
33. Martin, N.; Sanchez, L.; Illescas, B.; Perez, I. Chem. Rev. 1998, 98, 2527.
34. Hirsch, A., Ed. Fullerene and Related Structures; Springer: Berlin, 1999.
35. Al-Matar, H.; Abdul-Sada, A. K.; Avent, A. G.; Fowler, P. W.; Hitchcock, P. B.; Rogers, K. M.; Taylor, R. J. Chem. Soc., Perkin Trans. 2002, 2, 53.
36. Signorini, R.; Zerbetto, M.; Meneghetti, M.; Bozio, R.; Maggini, M.; De Faveri, C.; Prato, M.; Scorrano, G. Chem. Commun. 1996, 1891.
37. Maggini, M.; Faveri, C. D.; Scorrano, G.; Prato, M.; Brusatin, G.; Guglielmi, M.; Meneghetti, M.; Signorini, R.; Bozio R. Chem. Eur. 1999, 5, 2501.
38. Imahori, H.; Sakata, Y. Eur. J. Org. Chem. 1999, 2445, 5.
39. Guldi, D. M. Chem. Commun. 2000, 321.
40. Guldi, D. M.; Prato, M. Acc. Chem. Res. 2000, 33, 695.
41. Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40.
42. Kasermann, F.; Kempf, C. Antiviral. Res. 1997, 34, 65.
43. Ueng, T. H.; Kang, J. J.; Wang, H. W.; Cheng, Y. W.; Chiang, L. Y. Toxicol. Lett. 1997, 93, 29.
44. Friedman, S. H.; De Camp, D. L.; Sijbesma, R. P.; Srdanov, G.; Wudl, F.; Kenyon, G. I. J. Am. Chem. Soc. 1993, 115, 6506.
45. Chiang, L. Y.; Wang, L. Y.; Tseng, S. M.; Wu, J. S.; Hseih, K. H. Chem. Commun. 1994, 2675.
46. Chiang, L. Y.; Wang, L. Y.; Kuo, C. S. Macromolecules 1995, 28, 7574.
47. Ouyang, J.; Goh, S. H.; Elim, H. I.; Meng, G. C.; Ji, W. Chem. Phys. Lett. 2002, 366, 224.
48. Goswami, T. H.; Nandan, B.; Alam, S.; Mathur, G. N. Polymer 2003, 44, 3209.
49. Li, J.; Takeuchi, A.; Ozawa, M.; Li, X.; Saigo, K.; Kitazawa, K. J. Chem. Soc. Chem. Commun. 1993, 1784.
50. Estimation of the number of hydroxy groups per fullerene in fullerenol by thermal methods. Percentage weight loss due to dehydroxylation of polyols (150-570 °C) = 21; percentage weight loss due to structural degradation of fullerene plus char residue = 57; then number of hydroxy groups per fullerene = (720/57) × (21/17) = 15.6-16; similarly the number of acrylate groups attached to fullerene has been calculated.
51. Sun, Y. P.; Bin, M. Chem. Phys. Lett. 1995, 233, 57.
52. Zhang, T.; Xi, K.; Yu, X.; Gu, M.; Guo, S.; Gu, B.; Wang, H. Polymer 2003, 44, 2647.