Role of hydrogen bonding in the photophysical properties of isomeric tetrapyridylporphyrins in aprotic solvent

Journal of Physical Chemistry A

Volumn 115, Issue 5, 2011, Pages 631-642

  Kumar, Pippara Hemant ^a   Prashanthi, Suthari ^a   Bangal, Prakriti Ranjan ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

4-METHYLPHENOL; APROTIC SOLVENTS; DEUTERIUM ISOTOPE EFFECT; DICHLOROMETHANE SOLUTIONS; ELECTRON TRANSFER; ELECTRON WITHDRAWING GROUP; ELECTRON-DONATING GROUP; FLUORESCENCE BEHAVIORS; HYDROGEN BONDING POWER; HYDROGEN BONDINGS; HYDROGEN-BONDED COMPLEXES; ISOMERIC TETRAPYRIDYLPORPHYRINS; NON-RADIATIVE CHANNELS; ON DYNAMICS; PHENOL CONCENTRATION; PHOTO-INDUCED; PHOTOPHYSICAL PROPERTIES; PICOSECONDS; PORPHYRIN MACROCYCLE; PROTON COUPLED ELECTRON TRANSFERS; PYRIDYL; RADICAL ANIONS; RADICAL CATIONS; SPECTROSCOPIC TECHNIQUE; STATIC AND DYNAMIC; TEMPERATURE EFFECTS; TIME-RESOLVED FLUORESCENCE SPECTROSCOPY; TRANSIENT ABSORPTION; UV/ VIS SPECTROSCOPY;

ABSORPTION; ABSORPTION SPECTROSCOPY; BEHAVIORAL RESEARCH; DEUTERIUM; DICHLOROMETHANE; ELECTRON TRANSITIONS; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; FREE RADICAL REACTIONS; HYDROGEN; HYDROGEN BONDS; PORPHYRINS; QUENCHING;

PHENOLS;

EID: 79851493635     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp1045782     Document Type: Article

References (91)

1. Debus, R. J.; Barry, B. A.; Sithole, I.; Babcock, G. T.; McIntosh, L. Biochemistry 1988, 27, 9071-9074.
2. Hu, Y. Z.; Tsukiji, S.; Shinkai, S.; Oishi, S.; Hamachi, I. J. Am. Chem. Soc. 2000, 122, 241-253.
3. Kurreck, H.; Huber, M. Angew. Chem, Int. Ed 1995, 34, 849-866.
4. (a) Sundstrom, V.; Pullerits, T.; Grondelle, R. Van. J. Phys. Chem. B 1999, 103, 2327-2346.
5. (b) Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1995, 117, 704-714.
6. (a) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578-10592.
7. (b) Harriman, A.; Magda, D. J.; Sessler, J. L. J. Phys. Chem. 1991, 95, 1530-1532.
8. (a) Lukas, A. S.; Miller, S. E.; Wasielewski, M. R. J. Phys. Chem. B 2000, 104, 931-940.
9. (b) Balaban, T. S. Acc. Chem. Res. 2005, 38, 612-623.
10. (c) Balaban, M. C.; Eichhöfer, A.; Buth, G.; Hauschild, R.; Szmytkowski, J.; Kalt, H.; Balaban, T. S. J. Phys. Chem. B 2008, 112, 5512-5521.
11. Meat-Ner, M.; Adler, A. D. J. Am. Chem. Soc. 1975, 97, 5107-5111.
12. Dalton, J. L.; Milgrom, R.; Pemberton, S. M. J. Chem. Soc., Perkin Trans. 2 1980, 370-372.
13. De Luca, G.; Romeo, A.; Scolaro, L. M. J. Phys. Chem. B 2005, 109, 7149-7158.
14. Hu, J.-S.; Guo, Y.-G; Liang, H. P.; Wan, L.-J.; Jiang, L. J. Am. Chem. Soc. 2005, 127, 17090-17095.
15. Scolaro, L. M.; Romeo, A.; Castriciano, M. A.; De Luca, G.; Patane, S.; Micali, N. J. Am. Chem. Soc. 2003, 125, 2040-2041.
16. He, Y.; Borguet, E. Angew. Chem., Int. Ed. 2007, 46, 6098-6101.
17. Festschrift, M. K. J. Phys. Chem. 1991, 95, 10215-10220.
18. Herbich, J.; Hung, C. Y.; Thummel, R. P.; Waluk, J. J. Am. Chem. Soc. 1996, 118, 3508-3518.
19. Herek, J. L.; Pedersen, S.; Banares, L.; Zewail, A. H. J. Chem. Phys. 1992, 97, 9046-9061.
20. Flom, S. R.; Barbara, P. F. J. Phys. Chem. 1985, 89, 4489-4494.
21. Inoue, H.; Hida, M.; Nakashima, N.; Yoshihara, K. J. Phys. Chem. 1982, 86, 3184-3188.
22. Lin, S.; Struve, W. Photochem. Photobiol. 1991, 54, 61.
23. Schulman, S. G.; Liedke, P. J. Phys. Chem. 1973, 84, 317.
24. (a) Zaitsev, N. K.; Demyashkevich, A. B.; Kuzmin, M. G Khim. Vysok. Energ. 1978, 12, 430-433.
25. (b) Zaitsev, N. K.; Demyashkevich, A. B.; Kuzmin, M. G Khim. Vysok. Energ. 1979, 13, 331-334.
26. Miyasaka, H.; Tabata, A.; Kamada, K.; Mataga, N. J. Am. Chem. Soc. 1993, 115, 7335-7342, and references cited therein.
27. Diner, B. A.; Babcock, G. T. In Oxygenic Photosyntesis: The Light Reactions; Ort, D. R, Yocum, C. F., Eds.; Kluwer Academic: Dordrecht, The Netherlands, 1996; pp 213-247.
28. Hays, A. M. A.; Vassiliev, I. R.; Goldbeck, J. H.; Debus, R. J. Biochemistry 1998, 37, 11352-11365.
29. Cukier, R. I.; Nocera, D. G Annu. Rev. Phys. Chem. 1998, 49, 337-369.
30. Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363-390.
31. (a) Huynh, M. H. V.; Meyer, T. J. Chem. Rev. 2007, 107, 5004-5064.
32. (b) Meyer, T. J.; Huynh, M. H. V.; Thorp, H. H. Angew. Chem., Int. Ed. 2007, 46, 5284-5304.
33. (a) Marcus, R. A J. Chem. Phys. 1956, 24, 966-978.
34. (b) Marcus, RA. J. Chem. Phys. 1957, 26, 867-871.
35. (c) Marcus, R. A Discuss. Faraday Soc. 1960, 29, 21-31.
36. Rehn, D.; Weller, A. Isr. J. Chem. 1970, 8, 258-271.
37. Muller, A.; Ratajcak, H.; Junge, W.; Diemann, E. Electron and ProtonTransfer in Chemistry and Biology; Studies in Physical and Theoretical Chemistry; Elsevier: Amsterdam, 1992; Vol. 78.
38. Weller, A. Z. Electrochemistry 1956, 60, 1144.
39. (a) Cukier, R. I. J. Phys. Chem. 1994, 98, 2377-2381.
40. (b) Zhao, X. G.; Cukier, R. I. J. Phys. Chem. 1995, 99, 945-954.
41. (c) Cukier, R. I. J. Phys. Chem. 1996, 100, 15428-15443.
42. (a) Roth, J. P.; Yoder, J. C.; Won, T. J.; Mayer, J. M. Science 2001, 294, 2524-2526.
43. (b) Rhile, J. I.; Mayer, J. M. J. Am. Chem. Soc. 2004, 126, 12718-12719.
44. (c) Markle, F. T.; Mayer, J. M. Angew. Chem., Int. Ed. 2008, 47, 738-740.
45. (d) Rhile, I. J.; Markle, T. F.; Nagao, H.; Di Pasquale, A. G.; Lam, O. P.; Lockwood, M. A.; Rotter, K.; Mayer, J. M. J. Am. Chem. Soc. 2006, 128, 6075-6088.
46. (e) Mayer, J. M.; Rhile, I. J.; Larsen, F. B.; Mader, E. A.; Markle, T. F.; Di Pasquale, A. G Photosynth. Res. 2006, 87, 3-20.
47. (a) Soudackov, A. V.; Hammes-Schiffer, S. J. Chem. Phys. 1999, 111, 4672-4687.
48. (b) Soudackov, A. V.; Hammes-Schiffer, S. J. Chem. Phys. 2000, 113, 2385-2396.
49. (c) Hammes-Schiffer, S. Acc. Chem. Res. 2001, 34, 273-281.
50. (d) Carra, C.; Iordanova, N.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2003, 125, 10429-10436.
51. Hammes-Schiffer, S. Proton-Coupled Electron Transfer. In Electron Transfer in Chemistry Vol. I. Principles, Theories, Methods, and Techniques; Balzani, V., Ed.: Wiley-VCH: Weinheim, Germany, 2001; pp 189-214.
52. (a) Magnuson, A.; Frapart, Y.; Abrahamsson, M.; Horner, O.; Åkermark, B.; Sun, L.; Girerd, J. J.; Hammarström, L.; Styring, S. J. Am. Chem. Soc. 1999, 121, 89-96.
53. (b) Sjödin, M.; Styring, S.; Åkermark, B.; Sun, L.; Hammarström, L. J. Am. Chem. Soc. 2000, 122, 3932-3936.
54. (c) Sjödin, M.; Irebo, T.; Utas, J. E.; Lind, J.; Gabor Merényi, G.; Åkermark, B.; Hammarström, L. J. Am. Chem. Soc. 2006, 128, 13076-13083.
55. (a) Fecenko, C. J.; Thorp, H. H.; Meyer, T. J. J. Am. Chem. Soc. 2007, 129, 15098-15099.
56. (b) Concepcion, J. J.; Brennaman, M. K.; Deyton, J. R.; Lebedeva, N. V.; Forbes, M. D. E.; Papanikolas, J. M.; Meyer, T. J. J. Am. Chem. Soc. 2007, 129, 6968-6969.
57. (c) V. Hang Huyn, M.; Meyer, T. J.; White, D. P. S. J. Am. Chem. Soc. 1999, 121, 4530-4531.
58. (d) Lebeau, E. L.; Binstead, R. A.; Meyer, T. J. J. Am. Chem. Soc. 2001, 123, 10535-10544.
59. (a) Biczók, L.; Gupta, N.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 12601-12609.
60. (b) Biczók, L.; Bérces, T.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 11071-11077.
61. Su-Chun, H.; Macpherson, A. N.; Su, L.; Liddell, P. A.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D. J. Am. Chem. Soc. 1995, 117, 1657-1658.
62. Gentemann, S.; Medforth, C. J.; Forsyth, T. P.; Nurco, D. J.; Smith, KM.; Fajer, J.; Holten, D. J. Am. Chem. Soc 1994, 116, 7363-7368.
63. Gouterman, M. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. III, pp 1-165.
64. Mataga, N.; Tsuno, S. Bull. Chem. Soc. Jpn. 1957, 30, 368-374.
65. Ojadi, E. C. A.; Linschitz, H.; Gouterman, M.; Walter, R. I.; Lindsey, J. S.; Wagner, R. W.; Droupadi, P. R.; Wang, W. J. Phys. Chem. 1993, 97, 13192-13197.
66. Luca, G. D.; Romeo, A.; Scolaro, L. M. J. Phys. Chem. B 2005, 109, 7149-7158.
67. (a) Quimby, D. J.; Longo, F. R. J. Am. Chem. Soc. 1975, 97, 5111-5117.
68. (b) Zang, Y.; Wang, H.; Yang, R. H Sensor 2007, 7, 410-449.
69. Heitele, H.; Pöllinger, F.; Häberle, T.; Michel-Beyerle, M. E.; Staab, H. A. J. Phys. Chem. 1994, 98, 7402-7410.
70. Loutfy, R. O.; Loutfy, R. O. Can. J. Chem. 1973, 51, 1169-1171.
71. Prashanthi, S.; Hemant, P. K.; Wang, L.; Perepogu, A. K.; Bangal, P. R. J. Fluoresc. 2010, 20, 571-580.
72. Prashanthi, S.; Bangal, P. R. Chem. Commun. (Cambridge, U. K.) 2009, 1757-1759.
73. Costentin, C.; Robert, M.; Savnant, J. M. J. Am. Chem. Soc. 2006, 128, 8726-8727.
74. Gupta, N.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 6384-6391.
75. Sjödin, M.; Styring, S.; Wolpher, H.; Xu, Y.; Sun, L.; Hammarström, L. J. Am. Chem. Soc. 2005, 127, 3855-3863.
76. Reece, S. Y.; Nocera, D. F. J. Am. Chem. Soc. 2005, 127, 9448-9458.
77. Schenck, C. C.; Parson, W. W.; Holten, D.; Windsor, M. W.; Sarai, A. Biophys. J. 1981, 36, 479-489.
78. Smit, K. J.; Warman, J. M.; De Hass, M. P.; Paddon-row, M. N.; Oliver, A. M. Chem. Phys. Lett. 1988, 152, 177-182.
79. Heitel, H.; Finckh, P.; Ween, S.; Poellinger, F.; Michel-Beyerle, M. E. J. Phys. Chem. 1989, 93, 5173-5179.
80. Gunner, M. R.; Robertso, D. E.; Dutton, P. L. J. Phys. Chem. 1986, 90, 3783-3795.
81. Liang, N.; Miller, J. R.; Closs, G. L. J. Am. Chem. Soc. 1989, 111, 8740-8741.
82. Delaney, J. K.; Mauzerall, D. C.; Lindsay, J. S. J. Am. Chem. Soc. 1990, 112, 957-963.
83. Liang, N.; Miller, J. R.; Closs, G. L. J. Am. Chem. Soc. 1990, 112, 5353-5354.
84. O'Driscoll, E.; Simona, J. D.; Peters, K. S. J. Am. Chem. Soc. 1990, 112, 7091-7098.
85. Bixon, M.; Jortner, J. J. J. Phys. Chem. 1991, 95, 1941-1944.
86. Liu, J. Y.; Bolton, J. R. J. Phys. Chem. 1992, 96, 1718-1725.
87. Kroon, J.; Oevering, H.; Verhoeven, J. W.; Warmen, J. M.; Oliver, A. M.; Paddon-Row, M. W. J. Phys. Chem. 1993, 97, 5065-5069.
88. Liu, J.; Bolton, J. R. J. Phys. Chem. 1992, 96, 1718-1725.
89. Gadosy, T. A.; Shukla, D.; Johnston, L. J. J. Phys. Chem. A 1999, 103, 8834-8839.
90. (a) Chrystiuk, E.; Jusoh, A.; Santafianos, D.; Williams, A. J. Chem. Soc., Perkin Trans. 2 1986, 163-168.
91. (b) Tehan, B. J.; Lloyd, E. J.; Wong, M. G.; Pitt, W. R.; Montana, J. G.; Manallack, T. D.; Gancia, E Quant. Struct.-Act. Relat. 2002, 21, 457-472.