On the mechanism of photochromism of 4′-N, N-dimethylamino-7- hydroxyflavylium in Pluronic F127

Journal of Physical Chemistry B

Volumn 113, Issue 32, 2009, Pages 11134-11146

  Gomes, Raquel ^a   Laia, César A T ^a   Pina, Fernando ^a  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; CHARGE TRANSFER; CRITICAL MICELLE CONCENTRATION; ETHANOL; FLUORESCENCE; GELATION; GELS; GLYCEROL; ION EXCHANGE; PH EFFECTS; PHOTOCHROMISM; PHOTOISOMERIZATION; PHOTOLYSIS; SENSORS; SOLVENTS;

ABSORPTION WAVELENGTHS; ACIDIC PH VALUES; ACIDITY CONSTANTS; AQUEOUS PHASE; CHALCONES; CRITICAL MICELLE CONCENTRATION (CMC); CRITICAL MICELLE TEMPERATURE; CRITICAL TEMPERATURES; DIPOLAR MOMENT; DOMINANT PROCESS; FLASH PHOTOLYSIS; FLAVYLIUM; FLUORESCENCE MEASUREMENTS; FLUORESCENCE QUANTUM YIELD; HIGHLY POLAR SOLVENT; INTERNAL CHARGE TRANSFER; ISOMERIZATION YIELDS; LOCALLY EXCITED STATE; NEUTRAL PH; NONRADIATIVE PROCESS; PH-JUMP; PHOTOPHYSICS; PLURONIC F-127; PLURONIC MICELLES; PLURONICS; POLAR ENVIRONMENTS; PURE SOLVENTS; SOLVATOCHROMIC EFFECTS; SOLVENT POLARITY; STOKES SHIFT; TIME-RESOLVED; WATER PHASE;

MICELLES;

EID: 68549128684     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp902972q     Document Type: Article

References (64)

1. (a) Photochromism: Molecules and Systems; Bouas-Laurent, H., Dürr, H., Eds.; Elsevier: Amsterdam, The Netherlands, 1990.
2. (b) Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R., Eds.; Plenum: New York, 1999.
3. (c) Irie, M. Chem. Rev. 2000, 100, 1683-1684.
4. (d) Pina, F.; Maestri, M.; Balzani, V. Handbook of Photochemistry and Photobiology; American Scientific Publishers: Stevenson Ranch, CA, 2003; Chapter 9, Vol. 3, pp 411-449.
5. (a) Okada, H.; Nakajima, N.; Tanaka, T.; Iwamoto, M. Angew. Chem., Int. Ed. 2005, 44, 7233-7236.
6. (b) Bossi, M.; Belov, V.; Polyakova, S.; Hell, S. W. Angew. Chem., Int. Ed. 2006, 45, 7426-7465.
7. (c) Raymo, F. M.; Tomasulo, M. Chem. - Eur. J. 2006, 12, 3186-3193.
8. Raymo, F. M.; Tomasulo, M. Chem. - Eur. J. 2006, 12, 3186-3193.
9. Pina, F.; Melo, M. J.; Maestri, M.; Passaniti, P.; Balzani, V. J. Am. Chem. Soc. 2000, 122, 4496-4498.
10. (a) Pina, F.; Melo, M. J.; Maestri, M.; Ballardini, R.; Balzani, V. J. Am. Chem. Soc. 1997, 119, 5556-5561.
11. (b) Pina, F.; Roque, A.; Melo, M. J.; Maestri, M.; Belladelli, L.; Balzani, V. Chem. - Eur. J. 1998, 4, 1184-1191.
12. (c) Roque, A.; Lodeiro, C.; Pina, F.; Maestri, M.; Dumas, S.; Passaniti, P.; Balzani, V. J. Am. Chem. Soc. 2003, 125, 987-994.
13. (a) Brouillard, R. In The FlaVonoids: AdVances in Research; Harborne, J. B., Ed.; Chapman and Hall: London, 1988; p 525.
14. (b) Brouillard, R. In Anthocyanins as Food Colors; Markakis, P., Ed.; Academic Press: New York, 1982; Chapter 1.
15. Gomes, R.; Diniz, A. M.; Jesus, A.; Parola, A. J.; Pina, F. Dyes Pigm. 2009, 81, 69-79.
16. (a) Brouillard, R.; Dubois, J. E. J. Am. Chem. Soc. 1977, 99, 1359-1364.
17. (b) McClelland, R. A.; Gedge, S. J. Am. Chem. Soc. 1980, 102, 5838-5848.
18. (c) McClelland, R. A.; McGall, G. H. J. Org. Chem. 1982, 47, 3730-3736.
19. (a) Moncada, M. C.; Fernandez, D.; Lima, J. C.; Parola, A. J.; Lodeiro, C.; Folgosa, F.; Melo, M. J.; Pina, F. Org. Biomol. Chem. 2004, 2, 2802-2808.
20. (b) Giestas, L.; Folgosa, F.; Lima, J. C.; Parola, A. J.; Pina, F. Eur. J. Org. Chem. 2005, 418, 7-4200.
21. Figueiredo, P.; Lima, J. C.; Santos, H.; Wigand, M. C.; Brouillard, R.; Maçanita, A. L.; Pina, F. J. Am. Chem. Soc. 1994, 116, 1249-1254.
22. Wünscher, H.; Haucke, G.; Czerney, P.; Kurzer, U. J. Photochem. Photobiol., A: Chem. 2002, 151, 75-82.
23. (a) Matsushima, R.; Mizuno, H.; Itoh, H. J. Photochem. Photobiol., A: Chem. 1995, 89, 251-256.
24. (b) Matsushima, R.; Fujimoto, S.; Tokumura, K. Bull. Chem. Soc. Jpn. 2001, 74, 827-832.
25. Pina, F.; Parola, A. J.; Melo, M. J.; Laia, C. A. T.; Afonso, C. A. M. Chem. Commun. 2007, 1608-1610.
26. Gomes, R.; Parola, A. J.; Laia, C. A. T.; Pina, F. J. Phys. Chem. B 2007, 111, 12059-12065.
27. Pina, F.; Hatton, T. A. Langmuir 2008, 24, 2356-2364.
28. Alexandridis, P.; Hatton, T. A. Colloids Surf., A 1995, 96, 1-46.
29. Previous reference to this compound in the paper (a) Moncada, M. C.; Pina, F.; Roque, A.; Parola, A. J.; Maestri, M.; Balzani, V. Eur. J. Org. Chem. 2004, 2, 304-312.
30. Corrected in (b) Eur. J. Org. Chem. 2006, 4761. The present compound was synthesized for the first time in this work.
31. (a) Robinson, R.; Pratt, D. D. J. Chem. Soc. Trans. 1922, 121, 1577-1585.
32. (b) Robertson, A.; Robinson, R. J. Chem. Soc. 1926, 1713-1720.
33. Roque, A.; Lima, J. C.; Parola, A. J.; Pina, F. Photochem. Photobiol. Sci. 2007, 6, 381-385.
34. Küster, F. W.; Thiel, A. Tabelle per le Analisi Chimiche e Chimico-Fisiche, 12th ed.; Hoepli, Milano: Italy, 1982; Vol. 157, p 160.
35. Hatchard, C. G.; Parker, C. A. Proc. R. Soc. London, Ser. A 1956, 235, 518-36.
36. Pina, F.; Melo, M. J.; Ballardini, R.; Flamigni, L.; Maestri, M. New J. Chem. 1997, 21, 969-976.
37. Olmsted, J. J. Phys. Chem. 1979, 83, 2581-2584.
38. Montali, M.; Credi, A.; Prodi, L.; Gandolfi, M. T. Handbook of Photochemistry, 3rd ed.; Taylor & Francis, CRC Press: Boca Raton, FL, 2006.
39. Langhals, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 724.
40. Mataga, N.; Kubota, T. Molecular Interactions and Electronic Spectra; Marcel Dekker, Inc.: New York, 1970.
41. Diniz, A. M.; Gomes, R.; Laia, C. A. T.; Parola, A. J.; Pina, F. J. Phys. Chem. B 2009, 113, 719-727.
42. Fayed, T. A.; Awad, M. K. Chem. Phys. 2004, 317-326.
43. Rurack, K.; Dekhtyar, M. L.; Bricks, J. L.; Resch-Genger, U.; Rettig, W. J. Phys. Chem. A 1999, 103, 9626-9635.
44. Rurack, K.; Bricks, J. L.; Reck, G.; Radeglia, R.; Resch-Genger, U. J. Phys. Chem. A 2000, 104, 3087-3109.
45. Espagne, A.; Paik, D. H.; Changenet-Barret, P.; Martin, M. M.; Zewail, A. H. ChemPhysChem 2006, 7, 1717-1726.
46. Cazeau-Dubroca, C.; Lyazidi, S. A.; Cambou, P.; Peirigua, A.; Cazeau, P.; Pesquer, M. J. Chem. Phys. 1989, 93, 2347-2358.
47. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; Wiley VCH: New York, 1998; Chapter 7, pp 339-405.
48. Kamlet, M. J.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887.
49. Hicks, J.; Vandersall, M.; Babarogic, Z.; Eisenthal, K. B. Chem. Phys. Lett. 1985, 116, 18-24.
50. (a) Kwok, W.-M.; George, M. W.; Grills, D. C.; Ma, C.; Matousek, P.; Parker, A. W.; Phillips, D.; Toner, W. T.; Towrie, M. Angew. Chem, Int. Ed. 2003, 42, 1826-1830.
51. (b) Kwok, W.-M.; Ma, C.; George, M. W.; Grills, D. C.; Matousek, P.; Parker, A. W.; Phillips, D.; Toner, W. T.; Towrie, M. Photochem. Photobiol. Sci. 2007, 6, 987-994.
52. iso.
53. Haucke, G.; Czerney, P.; Steen, D.; Rettig, W.; Hartmann, H. Ber. Bunsen-Ges. Phys. Chem. 1993, 97, 561-570.
54. It was obtained through the fitting of a Lorentzian to the points near the maximum of the band.
55. Demchenko, A. P. Luminescence 2002, 17, 19-42.
56. Lacowicz, J. R.; Nakamoto, S. K. Biochemistry 1984, 23, 3013-3021.
57. Bagchi, B.; Fleming, G. R.; Oxtoby, D. W. J. Chem. Phys. 1983, 78, 7375-7385.
58. Prud'homme, R.; Wu, G.; Schneider, D. Langmuir 1996, 12, 4651.
59. Ghosh, S.; Adhikari, A.; Mandal, U.; Dey, S.; Bhattacharyya, K. J. Phys. Chem. C 2007, 111, 8775-8780.
60. Nikowa, L.; Schwarzer, D.; Troe, J.; Schroeder, J. J. Chem. Phys. 1992, 97, 4827-4835.
61. It is rather cumbersome to obtain a lifetime before irradiation since the measurement requires irradiation of the sample. In gels, the irradiation area is small, and stirring is not possible. Therefore, such measurement can only be performed in micelles.
62. Jeon, S.; Granick, S.; Kwon, K.; Char, K. Microviscosity 2002, 2883-2888.
63. (a) Linse, P.; Malmsten, M. Macromolecules 1992, 25, 5434-5439.
64. (b) Malmsten, M.; Lindman, B. Macromolecules 1992, 25, 5440-5445.