A spectroscopic and computational study of the singlet and triplet excited states of synthetic β-functionalized chlorins

Chemical Physics

Volumn 294, Issue 3, 2003, Pages 285-303

  Brückner, Christian ^a   McCarthy, Jason R ^a   Daniell, Heather W ^a   Pendon, Zeus D ^a   Ilagan, Robielyn P ^a   Francis, Tasha M ^a   Ren, Lei ^a   Birge, Robert R ^a   Frank, Harry A ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

EPR, electron paramagnetic resonance; HOMO, highest occupied molecular orbital; LUMO, lowest unoccupied molecular orbital; MO, molecular orbital; TPP, meso tetraphenylporphyrin (5,10,15,20 tetrakisphenylporhyrin)

Indexed keywords

2 HYDROXY 3 OXA 5,10,15,20 TETRAKISPHENYLCHLORIN; 2,3 DIOXO 5,10,15,20 TETRAKISPHENYLCHLORIN; 5,10,15,20 TETRAKISPHENYLCHLORIN; 5,10,15,20 TETRAKISPHENYLPORPHYRIN; CHLORINE DERIVATIVE; DIKETONE; PORPHYRIN; UNCLASSIFIED DRUG;

ABSORPTION; ABSORPTION SPECTROSCOPY; ARTICLE; CALCULATION; CHEMICAL BOND; CHROMATOPHORE; COMPARATIVE STUDY; ELECTRON SPIN RESONANCE; ELECTRONICS; FLUORESCENCE; MOLECULAR DYNAMICS; QUANTITATIVE ANALYSIS; SYNTHESIS;

EID: 17044452031     PISSN: 03010104     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0301-0104(03)00282-9     Document Type: Article

References (71)

1. Flitsch W. Adv. Heterocycl. Chem. 43:1988;73.
2. Fayer J. Chem. Ind. 1991;869.
3. Gouterman M. J. Mol. Spectrosc. 6:1961;138.
4. Kusch D., Töllner E., Lincke A., Montforts F.-P. Angew. Chem. Int. Ed. Engl. 34:1995;784.
5. Tomé A.C., Lacerda P.S.S., Neves M.G.P.M.S., Cavaleiro J.A.S. Chem. Commun. 1997;1199.
6. Shea K.M., Jaquinod L., Smith K.M. J. Org. Chem. 63:1998;7013.
7. Silva A.M.G., Tome A.C., Neves M.G.P.M.S., Silva A.M.S., Cavaleiro J.A.S. Chem. Commun. 1999;1767.
8. Desjardins A., Flemming J., Sternberg E.D., Dolphin D. Chem. Commun. 2002;2622.
9. McCarthy J.R., Jenkens H.A., Brückner C. Org. Lett. 5:2003;19.
10. Whitlock J. Jr., Hanamer R., Oester M.Y., Bower B.K. J. Am. Chem. Soc. 91:1969;7485.
11. Bonnett R., White R.D., Winfield U.-J., Berenbaum M.C. Biochem. J. 261:1989;277.
12. Bonnett R. Chem. Soc. Rev. 1995;19.
13. Sternberg E.D., Dolphin D., Brückner C. Tetrahedron. 54:1998;4151.
14. Pandey R.K., Zheng G. Guilard R. The Porphyrin Handbook. 2000;Academic Press, San Diego. p. 157.
15. Martin C.H., Birge R.R. J. Phys. Chem. A. 102:1998;852.
16. Ren L., Martin C.H., Wise K.J., Gillespie N.B., Luecke H., Lanyi J.K., Spudich J.L., Birge R.R. Biochemistry. 40:2001;13906.
17. Dolan P.M., Miller D., Cogdell R.J., Birge R.R., Frank H.A. J. Phys. Chem. B. 105:2001;12134.
18. Birge R.R., Gillespie N.B., Izaguirre E.W., Kusnetzow A., Lawrence A.F., Singh D., Song Q.W., Schmidt E., Stuart J.A., Seetharaman S., Wise K.J. J. Phys. Chem. B. 103:1999;10746.
19. Adler A.D., Longo F.R., Finarelli J.D., Goldmacher J., Assour J., Korsakoff L. J. Org. Chem. 32:1967;476.
20. Brückner C., Dolphin D. Tetrahedron Lett. 36:1995;3295.
21. Brückner C., Rettig S.J., Dolphin D. J. Org. Chem. 63:1998;2094.
22. Becke A.D. J. Chem. Phys. 98:1993;5648.
23. Lee C., Yang W., Parr R.G. Phys. Rev. B. 37:1988;785.
24. Parr R.G., Yang W. Density-Functional Theory of Atoms and Molecules. 1989.
25. Sham L.J., Kohn W. Phys. Rev. 145:1966;561.
26. Kohn W., Sham L.J. Phys. Rev. 137:1965;1697.
27. Kohn W., Sham L.J. Self-Consistent Equations Including Exchange and Correlation Effects. 1965;University of California, San Diego. p. 21.
28. Frisch M.J.et al. Gaussian 98. 1998;Gaussian Inc, Pittsburgh, PA.
29. Zerner M.C., Loew G.H., Kirchner R.F., Mueller-Westerhoff U.T. J. Am. Chem. Soc. 102:1980;589.
30. Zerner M.C. Rev. Comput. Chem. 2:1991;313.
31. Thompson M.A., Zerner M.C. J. Am. Chem. Soc. 113:1991;8210.
32. Crossley M.J., King L.G. J. Chem. Soc., Chem. Commun. 1984;920.
33. Crossley M.J., Hambley T.W., King L.G. Bull. Soc. Chim. Fr. 133:1996;735.
34. Gouterman M., Hall R.J., Khalil G.-E., Martin P.C., Shankland E.G., Cerny R.L. J. Am. Chem. Soc. 111:1989;3702.
35. Jayaraj K., Gold A., Austin R.N., Ball L.M., Terner J., Mandon D., Weiss R., Fischer J., DeCian A., Bill E., Müther M., Schünemann V., Trautwein A.X. Inorg. Chem. 36:1997;4555.
36. Khalil G., Gouterman M., Ching S., Costin C., Coyle L., Gouin S., Green E., Sadilek M., Wan R., Yearyean J., Zelelow B., Porphyrins J. Phtalocyanines. 6:2002;135.
37. Daniell H.D., Williams S.C., Jenkins H.A., Brückner C. Tetrahedron Lett. 44:2003;4045.
38. Crossley M.J., Burn P.L., Langford S.J., Pyke S.M., Stark A.G. J. Chem. Soc. Chem. Commun. 1991;1567.
39. Vannelli T.A., Karpishin T.B. Inorg. Chem. 38:1999;2246.
40. Crossley M.J., Johnston L.A. Chem. Commun. 2002;1122.
41. Belair J.P., Ziegler C.J., Rajesh C.S., Modarelli D.A. J. Phys. Chem. A. 106:2002;6445.
42. Gassman P.G., Ghosh A., Almlof J. J. Am. Chem. Soc. 114:1992;9990.
43. Ghosh A. J. Porphyrins Phthalocyanines. 5:2001;187.
44. Ma S.Y., Li Z.H., Liu R.Z. Theochemistry. 528:2000;121.
45. Parusel A.B.J., Grimme S. J. Porphyrins Phthalocyanines. 5:2001;225.
46. Vitasovic M., Gouterman M., Linschitz H. J. Porphyrins Phthalocyanines. 5:2001;191.
47. Van der Bent S.J., Schaafsma T.J. Chem. Phys. Lett. 35:1975;45.
48. Clarke R.H., Frank H.A. J. Chem. Phys. 65:1976;39.
49. Connors R.E., Leenstra W.R. Clarke R.H. Triplet State ODMR Spectroscopy. 1982;Wiley, New York.
50. Budil D.E., Thurnauer M.C. Biochim. Biophys. Acta. 1057:1991;1.
51. Van Dorp W.G., Schaafsma T.J., Soma M., Van der Waals J.H. Chem. Phys. Lett. 21:1973;221.
52. Kleibeuker J.F., Platenkamp R.J., Schaafsma T.J. Chem. Phys. Lett. 41:1976;557.
53. Connors R.E., Durand R.R., Borowski K.J. Chem. Phys. Lett. 69:1980;559.
54. Clarke R.H., Connors R.E. J. Chem. Phys. 62:1975;1600.
55. Clarke R.H., Connors R.E., Schaafsma T.J., Kleibeuker J.F., Platenkamp R.J. J. Am. Chem. Soc. 98:1976;3674.
56. Clarke R.H., Frank H.A. Chem. Phys. Lett. 51:1977;13.
57. Antheunis D.A., Schmidt J., Van der Waals J.H. Mol. Phys. 27:1974;1521.
58. Metz F., Friedrich S., Hohlneicher G. Chem. Phys. Lett. 16:1972;353.
59. Moore T.A., Benin D., Roderick T. J. Am. Chem. Soc. 104:1982;7356.
60. Harriman A., Porter G., Searle N. J. Chem. Soc., Faraday Trans. 2:1979;1515.
61. Gouterman M., Khalil G. J. Mol. Spectrosc. 53:1974;88.
62. Dolphin D. The Porphyrins. 1978;Academic Press, New York.
63. Thurnauer M.C., Katz J.J., Norris J.R. Proc. Natl. Acad. Sci. USA. 72:1975;3270.
64. Kleibeuker J.F. The Molecular Photophysics of Chlorophyll. A Study of its Triplet State. 1977;Agricultural University, Wageningen.
65. Ake R.L., Gouterman M. Theor. Chim. Acta. 15:1969;20.
66. Langhoff S.R., Davidson E.R., Gouterman M., Leenstra W.R., Kwiram A.L. J. Chem. Phys. 62:1975;169.
67. Shediac R., Gray M.H.B., Uyeda H.T., Johnson R.C., Hupp J.T., Angiolillo P.J., Therien M.J. J. Am. Chem. Soc. 122:2000;7017.
68. Levanon H., Wolberg A. Chem. Phys. Lett. 24:1974;96.
69. Pekkarinen L., Linschitz H. J. Am. Chem. Soc. 82:1960;2407.
70. Nissani E., Scherz A., Levanon H. Photochem. Photobiol. 25:1977;93.
71. Keegan J.D., Stolzenberg A.M., Lu Y.-C., Linder R.E., Barth G., Moscowitz A., Bunnenberg E., Djerassi C. J. Am. Chem. Soc. 104:1982;4305.