Thermoreversible polymerization. Formation of fullerene-diene oligomers and copolymers

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1455-1458

  Ilhan, Faysal ^a   Rotello, Vincent M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; COPOLYMER; FULLERENE DERIVATIVE; MONOMER; OLIGOMER;

ARTICLE; DECOMPOSITION; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; POLYMERIZATION; REDUCTION;

EID: 0033525497     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9814849     Document Type: Article

References (45)

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26. For examples of fullerene-containing polymers, see: Hawker, C.; Wooley, K.; Fréchet, J. J. Chem. Soc. Chem. Commun. 1994, 925. Weis, C.; Friederich, C.; Mülhaupt, R.; Frey, H. Macromolecules 1995, 28, 403. Zhang, N.; Schricker, S.; Wudl, F.; Prato, M.; Maggini, M.; Scorrano, G. Chem. Mater. 1995, 7, 441-442. Dai, L.; Mau, A.; Griesser, H.; Spurling, T.; White, J. J. Phys. Chem. 1995, 99, 17302. Wang, J.; Javaher, G.; Petrie, S.; Bohme, D. K. J. Am. Chem. Soc., 1992, 114, 9665. Hawker, C. J.; Wooley, K. L.; Frechet, J. M. J. J. Chem. Soc., Chem. Commun. 1994, 925. Stephens, P. W.; Bortel, G.; Faigel, G.; Tegze, M.; Janossy, A.; Pekker, S.; Oszlanyi, G.; Forro, L. Nature, 1994, 370, 637. Wang, Y.; Holden, J. M.; Bi, X.; Eklund, P. C. Chem. Phys. Lett. 1994, 217, 413. Loy, D.; Assink, R. A. J. Am. Chem. Soc. 1992, 114, 3977. Sun, Y.; Ma, B.; Bunker, C.; Liu, B. J. Am. Chem. Soc. 1996, 117, 12706. Zheng, J.; Goh, S. H.; Lee, S. Y. Macromolecules 1997, 30, 8069. Sun, Y.-P.; Lawson, G. E.; Bunker, C. E.; Johnson, R. A.; Ma, B.; Farmer, C.; Riggs, J. E.; Kitaygorodskiy, A. Macromolecules 1996, 29, 8441.
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29. For examples of irreversible fullerene Diels-Alder reactions, see: Belik, P.; Gügel, A.; Spickerman, J.; Müllen, K. Angew. Chem., Intl. Ed. Engl. 1993, 32, 78. Rubin, Y.; Khan, S.; Freedberg, D.; Yeretzian, C. J. Am. Chem. Soc. 1993, 115, 344. Herrmann, A.; Diederich, F.; Thilgen, C.; ter Meer, H.; Müller, G. Helv. Chim. Acta 1994, 77, 1689. Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1995, 6899.
30. For examples of irreversible fullerene Diels-Alder reactions, see: Belik, P.; Gügel, A.; Spickerman, J.; Müllen, K. Angew. Chem., Intl. Ed. Engl. 1993, 32, 78. Rubin, Y.; Khan, S.; Freedberg, D.; Yeretzian, C. J. Am. Chem. Soc. 1993, 115, 344. Herrmann, A.; Diederich, F.; Thilgen, C.; ter Meer, H.; Müller, G. Helv. Chim. Acta 1994, 77, 1689. Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1995, 6899.
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33. 60 with anthracene at elevated temperatures; this has been shown to be unnecessary (refs 4e, 7).
34. 60 with anthracene at elevated temperatures; this has been shown to be unnecessary (refs 4e, 7).
35. 60 (ref 7). It likely that these reactions did not occur during heating but upon cooling after reaction.
36. -1.
37. 60 in the GPC chromatogram.
38. The completion of depolymerization was verified by HPLC analysis in which all of the oligomeric and polymeric peaks disappeared.
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40. 60 in solution. This arises from the enhanced mobility and accessibility of the monomeric fullerene.
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