Memory effects based on intermolecular photoinduced proton transfer

Journal of the American Chemical Society

Volumn 125, Issue 8, 2003, Pages 2361-2364

  Raymo, Françisco M ^a   Alvarado, Robert J ^a   Giordani, Silvia ^a   Cejas, Mabel A ^a  

^a University of Miami   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOINDUCED PROTON TRANSFER;

IRRADIATION; LIGHT; ORGANIC COMPOUNDS; REDUCTION;

MOLECULAR PHYSICS;

MEROCYANINE; PYRAN DERIVATIVE; SPIROPYRAN; UNCLASSIFIED DRUG;

ARTICLE; ELECTRIC CURRENT; EQUILIBRIUM CONSTANT; IRRADIATION; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; PROTON TRANSPORT; THERMAL ANALYSIS; TRANSPORT KINETICS;

BENZOPYRANS; BIOMIMETIC MATERIALS; INDOLES; NITRO COMPOUNDS; PHOTOCHEMISTRY; PROTONS; PYRIDINIUM COMPOUNDS; PYRIMIDINONES;

EID: 0037466993     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027977j     Document Type: Article

References (66)

1. Guyton, A. C.; Hall, J. E. Human Physiology and Mechanisms of Disease; W. B. Saunders Company: Philadelphia, PA, 1997.
2. Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
3. (a) Fabbrizzi, L.; Licchelli, M.; Pallavicini, P. Acc. Chem. Res. 1999, 32, 846-853.
4. (b) Willner, I.; Katz, E. Angew. Chem., Int. Ed. 2000, 39, 1180-1218.
5. (c) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348-3391.
6. (d) Irie, M. Chem. Rev. 2000, 100, 1685-1716.
7. (e) Yokoyama, Y. Chem. Rev. 2000, 100, 1717-1740.
8. (f) Berkovic, G.; Krongauz, V.; Weiss, V. Chem. Rev. 2000, 100, 1741-1754.
9. (g) Feringa, B. L.; van Delden, R. A.; Koumura, N.; Geertsema, E. M. Chem. Rev. 2000, 100, 1789-1816.
10. (h) Feringa, B. L. Acc. Chem. Res. 2001, 34, 504-513.
11. (i) Diederich, F. Chem. Commun. 2001, 219-227.
12. (a) Ward, M. D. J. Chem. Educ. 2001, 78, 321-328.
13. (b) de Silva, A. P.; McClenaghan, N. D.; McCoy, C. P. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; pp 156-185.
14. (c) de Silva, A. P.; McClean, G. D.; McClenaghan, N. D.; Moody, T. S.; Weir, S. M. Nachr. Chem. 2001, 49, 602-606.
15. (d) de Silva, A. P.; Fox, D. B.; Moody, T. S.; Weir, S. Pure Appl. Chem. 2001, 73, 503-511.
16. (e) Raymo, F. M. Adv. Mater. 2002, 14, 401-414.
17. Mitchell, R. J. Microprocessor Systems: An Introduction; Macmillan: London, 1995.
18. (a) de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. Nature 1993, 364, 42-44.
19. (b) de Silva, A. P.; Gunaratne, H. Q. N.; Maguire, G. E. M. J. Chem. Soc., Chem. Commun. 1994, 1213-1214.
20. (c) de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. J. Am. Chem. Soc. 1997, 119, 7891-7892.
21. (d) de Silva, A. P.; Dixon, I. M.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Maxwell, P. R. S.; Rice, T. E. J. Am. Chem. Soc. 1999, 121, 1393-1394.
22. (e) de Silva, A. P.; McClenaghan, N. D. J. Am. Chem. Soc. 2000, 122, 3965-3966.
23. (f) Brown, G. J.; de Silva, A. P.; Pagliari, S. Chem. Commun. 2002, 2461-2464.
24. Iwata, I.; Tanaka, K. J. Chem. Soc., Chem. Commun. 1995, 1491-1492.
25. (a) Ghosh, P.; Bharadwaj, P. K.; Mandal, S.; Ghosh, S. J. Am. Chem. Soc. 1996, 118, 1553-1554.
26. (b) Ghosh, P.; Bharadwaj, P. K.; Roy, J.; Ghosh, S. J. Am. Chem. Soc. 1997, 119, 11903-11909.
27. Cooper, C. R.; James, T. D. Chem. Commun. 1997, 1419-1420.
28. (a) Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Mattersteig, G.; Matthews, O. A.; Montalti, M.; Spencer, N.; Stoddart, J. F.; Venturi, M. Chem. Eur. J. 1997, 3, 1992-1996.
29. (b) Credi, A.; Balzani, V.; Langford, S. J.; Stoddart, J. F. J. Am. Chem. Soc. 1997, 119, 2679-2681.
30. (a) Pina, F.; Roque, A.; Melo, M. J.; Maestri, I.; Belladelli, L.; Balzani, V. Chem. Eur. J. 1998, 4, 1184-1191.
31. (b) Pina, F.; Maestri, M.; Balzani, V. Chem. Commun. 1999, 107-114.
32. (c) Roque, A.; Pina, F.; Alves, S.; Ballardini, R.; Maestri, M.; Balzani, V. J. Mater. Chem. 1999, 9, 2265-2269.
33. (d) Pina, F.; Melo, M. J.; Maestri, M.; Passaniti, P.; Balzani, V. J. Am. Chem. Soc. 2000, 122, 4496-4498.
34. (e) Alves, S.; Pina, F.; Albeda, M. T.; García-España, E.; Soriano, C.; Luis, S. V. Eur. J. Inorg. Chem. 2001, 405-412.
35. Inouye, M.; Akamatsu, K.; Nakazumi, H. J. Am. Chem. Soc. 1997, 119, 9160-9165.
36. (a) Parker, D.; Williams, J. A. G. Chem. Commun. 1998, 245-246.
37. (b) Gunnlaugsson, T.; MacDónail, D. A.; Parker, D. Chem. Commun. 2000, 93-94.
38. (c) Gunnlaugsson, T.; MacDónail, D. A.; Parker, D. J. Am. Chem. Soc. 2001, 123, 12866-12876.
39. Patolsky, F.; Filanovsky, B.; Katz, E.; Willner, I. J. Phys. Chem. B 1998, 102, 10359-10367.
40. Kuciauskas, D.; Liddell, P. A.; Moore, A. L.; Moore, T. A.; Gust, D. J. Am. Chem. Soc. 1998, 120, 10880-10886.
41. (a) Gobbi, L.; Seiler, P.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 674-678.
42. (b) Gobbi, L.; Seiler, P.; Diederich, F.; Gramlich, V.; Boudon, C.; Gisselbrecht, J. P.; Gross, M. Helv. Chim. Acta 2001, 84, 743-777.
43. (a) Ji, H. F.; Dabestani, R.; Brown, G. M. J. Am. Chem. Soc. 2000, 122, 9306-9307.
44. (b) Xu, H.; Xu, X.; Dabestani, R.; Brown, G. M.; Fan, L.; Patton, S.; Ji, H.-F. J. Chem. Soc., Perkin Trans. 2 2002, 636-643.
45. Baytekin, H. T.; Akkaya, E. U. Org. Lett. 2000, 2, 1725-1727.
46. Lukas, A. S.; Bushard, P. J.; Wasielewski, M. R. J. Am. Chem. Soc. 2001, 123, 2440-2441.
47. (a) Raymo, F. M.; Giordani, S. J. Am. Chem. Soc. 2001, 123, 4651-4652.
48. (b) Raymo, F. M.; Giordani, S. Org. Lett. 2001, 3, 1833-1836.
49. (c) Raymo, F. M.; Giordani, S. Org. Lett. 2001, 3, 3475-3478.
50. (d) Raymo, F. M.; Giordani, S. J. Am. Chem. Soc. 2002, 124, 2004-2007.
51. (e) Raymo, F. M.; Giordani, S. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4941-4944.
52. (a) Kompa, K. L.; Levine, R. D. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 410-414.
53. (b) Witte, T.; Bucher, C.; Remacle, F.; Proch, D.; Kompa, K. L.; Levine, R. D. Angew. Chem., Int. Ed. 2001, 40, 2512-2514.
54. (c) Remacle, F.; Levine, R. D. J. Chem. Phys. 2001, 114, 10239-10246.
55. (d) Remacle, F.; Speiser, S.; Levine, R. D. J. Phys. Chem. B 2001, 105, 5589-5591.
56. (e) Steintz, D.; Remacle, F.; Levine, R. D. ChemPhysChem 2002, 43-51.
57. de Silva, S. A.; Amorelli, B.; Isidor, D. C.; Loo, K. C.; Crooker, K. E.; Pena, Y. E. Chem. Commun. 2002, 1360-1361.
58. Reed, M. A.; Chen, J.; Rawlett, A. M.; Price, D. W.; Tour, J. M. Appl. Phys. Lett. 2001, 78, 3735-3737.
59. Luo, Y.; Collier, C. P.; Jeppesen, J. O.; Nielsen, K. A.; Delonno, E.; Ho, G.; Perkins, J.; Tseng, H. R.; Yamamoto, T.; Stoddart, J. F.; Heath, J. R. ChemPhysChem 2002, 3, 519-525.
60. (a) Guglielmetti, R. In Photochromism: Molecules and Systems; Dürr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; pp 314-466 and 855-878.
61. (b) Willner, I.; Willner, B. In Bioorganic Photochemistry; Morrison, H., Ed.; Wiley: New York, 1993; pp 1-110.
62. (c) Winkler, J. D.; Deshayes, K.; Shao, B. In Bioorganic Photochemistry; Morrison, H., Ed.; Wiley: New York, 1993; pp 169-196.
63. (d) Bertelson, R. C. In Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R., Eds.; Plenum Press: New York, 1999; pp 11-83.
64. (e) Berkovic, G.; Krongauz, V.; Weiss, V. Chem. Rev. 2000, 100, 1741-1754.
65. (f) Tamai, N.; Miyasaka, H. Chem. Rev. 2000, 100, 1875-1890.
66. Monk, P. M. S. The Viologens: Physicochemical Properties, Synthesis and Applications of the Salts of 4,4′-Bipyridine; Wiley: New York, 1998.