Photocapture of dynamic hydrogen-bonded assemblies

International Journal of Photoenergy

Volumn 6, Issue 4, 2004, Pages 185-192

  McClenaghan, Nathan D ^a   Bassani, Dario M ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; SUPRAMOLECULAR CHEMISTRY;

COVALENT SYSTEMS; DYNAMIC ASSEMBLY; HYDROGEN BONDING INTERACTIONS; HYDROGEN BONDING MOTIFS; HYDROGEN-BONDED ASSEMBLIES; NONCOVALENT; PHOTODIMERIZATION; SUPRAMOLECULAR ASSEMBLIES; SUPRAMOLECULAR TEMPLATES; WEAK HYDROGEN BONDING;

STYRENE;

EID: 24044451218     PISSN: 1110662X     EISSN: 1110662X     Source Type: Journal    
DOI: 10.1155/S1110662X04000236     Document Type: Conference Paper

References (56)

1. G. M. J. Schmidt, Pure Appl. Chem. 27 (1971), 647;
2. Y. Ito, Molecular and Supramolecular Photochemistry, Vol. 3, (V. Ramamurthy and K. S. Schanze, Eds.), Marcel Dekker, New York, 1999.
3. J.-M. Lehn, Chem. Eur. J. 6 (2000), 2097;
4. J.-M. Lehn, Supramolecular Chemistry-Concepts and Perspectives,VCH, Weinheim, 1995.
5. M. Yoshizawa, Y. Takeyama, T. Kusukawa, and M. Fujita, Angew. Chem., Int. Ed. 41 (2002), 1347.
6. For a discussion of the mechanism of cinnamate photodimerization see: D. M. Bassani, CRC Handbook of Organic Photochemistry and Photobiology, 2nd Ed., (W. Horspool and F. Lenci, Eds.), 2003, Chapter 20;
7. F. D. Lewis, S. L. Quillen, J. E. Elbert, S. Schneider, and P. Geiselhart, J. Photochem. Photobiol. A 47 (1989), 173.
8. P. Beak and J. M. Ziegler, J. Org. Chem. 46 (1981), 619.
9. T. Bach, H. Bergmann, and K. Harms, Org. Lett. 3 (2001), 601.
10. K. S. Feldman, R. F. Campbell, J. C. Saunders, C. Ahn, and K. M. Masters, J. Org. Chem. 62 (1997), 8814.
11. T. Nakamura, K. Takagi, and Y. Sawaki, Bull. Chem. Soc. Jpn. 71 (1998), 909;
12. K. Takagi, H. Fukaya, N. Miyake, and Y. Sawaki, Chem. Lett. (1988), 1053;
13. Y. Nakamura, J. Chem. Soc., Chem. Commun. (1988), 477;
14. O. Ohtani, R. Sasai, T. Adachi, I. Hatta, and K. Takagi, Langmuir 18 (2002), 1165.
15. J. Zhao, H. R. Hafiz, H. Akiyama, K. Tamada, and F. Nakanishi, Mol. Cryst. Liq. Cryst. A 322 (1998), 233;
16. J. Zhao, H. Akiyama, K. Abe, Z. Liu, and F. Nakanishi, Langmuir 16 (2000), 2275;
17. J. Zhao, K. Abe, H. Akiyama, Z. Liu, and F. Nakanishi, Langmuir 15 (1999), 2543;
18. M. Yamamoto, N. Furuyama, and K. Itoh, J. Phys. Chem. 100 (1996), 18483.
19. J. N. Moorthy, K. Venkatesan, and R. G. Weiss, J. Org. Chem. 57 (1992), 3292;
20. T. J. Brett, J. M. Alexander, and J. J. Stezowski, J. Chem. Soc., Perkin Trans. 2 (2000), 1095;
21. T. J. Brett, J. M. Alexander, and J. J. Stezowski, J. Chem. Soc., Perkin Trans. 2 (2000), 1105.
22. E. E. Simanek, X. Li, I. S. Choi, and G. M. Whitesides, Comprehensive Supramolecular Chemistry, (J.-M. Lehn, Ed.), Pergamon, New York, Vol. 9, 1996, Chapter 17.
23. D. M. Bassani, V. Darcos, S. Mahony, and J.-P. Desvergne, J. Am. Chem. Soc. 122 (2000), 8795.
24. H. Greiving, H. Hopf, P. G. Jones, P. Bubenitschek, J.-P. Desvergne, and H. Bouas-Laurent, Liebigs Ann. (1995), 1949.
25. V. Darcos, K. Griffith, X. Sallenave, J.-P. Desvergne, C. Guyard-Duhaon, B. Hasenknopf, and D. M. Bassani, Photochem. Photobiol. Sci. (2003), 1152.
26. The program EQNMR was used to fit the experimental data. M. J. Hynes, J. Chem. Soc., Dalton Trans. (1993), 311.
27. K. A. Connors, Binding Constants, Wiley Interscience, New York, 1987.
28. J. A. Zerkowski, J. C. MacDonald, C. T. Seto, D. A. Wierda, and G. M. Whitesides, J. Am. Chem. Soc. 116 (1994), 2382.
29. J. C. Dalton and J. J. Snyder, Mol. Photochem. 6 (1974), 291.
30. See for example:- G. Vlatakis, L. I. Andersson, R. Muller, and K. Mosbach, Nature 361 (1993), 645;
31. J.-D. Marty, M. Mauzac, C. Fournier, I. Rico-Lattes, and A. Lattes, Liq. Cryst. 29 (2002), 529.
32. J. Damen and D. C. Neckers, J. Am. Chem. Soc. 102 (1980), 3265.
33. D. M. Bassani, X. Sallenave, V. Darcos, and J.-P. Desvergne, Chem. Commun. (2001), 1446.
34. S. R. Collinson, T. Gelbrich, M. B. Hursthouse, and J. H. R. Tucker, Chem. Commun. (2001), 555;
35. S. K. Chang, D. Van Engen, E. Fan, and D. A. Hamilton, J. Am. Chem. Soc. 113 (1991), 7640.
36. A. M. Rao, P. Zhou, K. A. Wang, G. T. Hager, J. M. Holden, Y. Wang, W. T. Lee, X.-X. Bi, P. C. Eklund, D. S. Cornett, M. A. Duncan, and I. J. Amster, Science 259 (1993), 955;
37. P. Zhou, Z.-H. Dong, A. M. Rao, and P. C. Eklund, Chem. Phys. Lett. 211 (1993), 337;
38. Y.-P. Sun, B. Ma, C. E. Bunker, and B. Liu, J. Am. Chem. Soc. 117 (1995), 12705.
39. Y. Wang, J. M. Holden, Z.-H. Dong, X. X. Bi, and P. C. Eklund, Chem. Phys. Lett. 211 (1993), 341.
40. J. Knol and J. C. Hummelen, J. Am. Chem. Soc. 122 (2000), 3226.
41. N. D. McClenaghan, C. Absalon, and D. M. Bassani, J. Am. Chem. Soc. 125 (2003), 13004.
42. 2v symmetry.
43. A. P. G. Robinson, R. E. Palmer, T. Tada, T. Kanayama, J. A. Preece, D. Philp, U. Jonas, and F. Diederich, Chem. Phys. Lett. 289 (1998), 586;
44. I. Lamparth, G. Schick, and A. Hirsch, Liebigs. Ann./Recueil (1997), 253.
45. D. M. Bassani, N. D. McClenaghan et al., in preparation.
46. Other hydrogen-bonding fullerenes:- L. Sánchez, M. T. Rispens, and J. C. Hummelen, Angew. Chem., Int. Ed. 41 (2002), 838;
47. M. T. Rispens, L. Sánchez, J. Knol, and J. C. Hummelen, Chem. Commun. (2001), 161;
48. J. J. González, S. González, E. M. Priego, C. Luo, D. M. Guldi, J. de Mendoza, and N. Martín, Chem. Commun. (2001), 163;
49. Z. Shi, Y. Li, H. Gong, M. Liu, S. Xiao, H. Liu, H. Li, S. Xiao, and D. Zhu, Org. Lett. 4 (2002), 1179;
50. S. Xiao, Y. Li, H. Fang, H. Li, H. Liu, Z. Shi, L. Jiang, and D. Zhu, Org. Lett. 4 (2002), 3063;
51. F. Diederich, L. Echegoyen, M. Gómez-López, R. Kessinger, and J. F. Stoddart, J. Chem. Soc., Perkin Trans. 2 (1999), 1577;
52. E. H. A. Beckers, A. P. H. J. Schenning, P. A. van Hal, A. El-ghayoury, L. Sánchez, J. C. Hummelen, E. W. Meijer, and R. A. J. Janssen, Chem. Commun. (2002), 2888;
53. D. M. Guldi, J. Ramey, M. V. Martínez-Díaz, A. de la Escosura, T. Torres, T. Da Ros, and M. Prato, Chem. Commun. (2002), 2774;
54. M. Gutiérrez-Nava, H. Nierengarten, P. Masson, A. Van Dorsselar, and J.-F. Nierengarten, Tet. Lett. 44 (2003), 3043.
55. A. Hirsch, I. Lamparth, and V. Karfunkel, Angew. Chem., Int. Ed. 106 (1994), 453.
56. II-pyridine interactions: M. El Bakkari, N. D. McClenaghan, and J.-M. Vincent, J. Am. Chem. Soc. 124 (2002), 12942.