The remarkable ability of B3LYP/3-21G(*) calculations to describe geometry, spectral and electrochemical properties of molecular and supramolecular porphyrin-fullerene conjugates

Comptes Rendus Chimie

Volumn 9, Issue 7-8, 2006, Pages 960-981

  Zandler, Melvin E ^a   D'Souza, Francis ^a  

^a WICHITA STATE UNIVERSITY   (United States)

Author keywords

Axial coordination; B3LYP 3 21G(*); Base pairing; DFT calculations; Dyad; Fullerene; HOMO LUMO; Porphyrin; Self assembly; Supramolecule; Triad

Indexed keywords

EID: 33646498101     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2005.12.008     Document Type: Short Survey

References (66)

1. Imahori H., and Sakata Y. Adv. Mater. 9 (1997) 537
2. Boyd P.D.W., and Reed C.A. Acc. Chem. Res. 38 (2005) 235
3. Imahori H., and Sakata Y. Eur. J. Org. Chem. (1999) 2445
4. Guldi D.M. Pure Appl. Chem. 75 (2003) 1069
5. Guldi D.M. Chem. Commun. (2000) 321
6. Prato M., and Maggini M. Acc. Chem. Res. 31 (1998) 519
7. Martin N., Sanchez L., Illescas B.M., and Perez I. Chem. Rev. 98 (1998) 2527
8. Sanchez L., Martin N., and Guldi D.M. Angew. Chem., Int. Ed. Engl. 44 (2005) 5374
9. El-Khouly M.E., Ito O., Smith P.M., and D'Souza F. J. Photochem. Photobiol. C: Photochem. Rev. 5 (2004) 79
10. D'Souza F., and Ito O. Coord. Chem. Rev. 249 (2005) 1410
11. Gust D., Moore T.A., and Moore A.L. Acc. Chem. Res. 34 (2001) 40
12. Meijer M.D., van Klink G.P.M., and van Koten G. Coord. Chem. Rev. 230 (2002) 141
13. Gaussian 03 (Revision B-04), M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian, Inc., Pittsburgh, PA, 2003.
14. Kim K.S., Tarakeshwar P., and Lee J.Y. Chem. Rev. 100 (2000) 4145
15. Jensen K.P., and Ryde U. J. Phys. Chem. A 107 (2003) 7539
16. Xu X., Zhang Q., Muller R.P., and Goddard III W.A. J. Chem. Phys. 122 (2005) 14105
17. Cerny J., and Hobza P. See, however, failure for stacked complexes. Phys. Chem. Chem. Phys. 7 (2005) 1626
18. D'Souza F., Zandler M.E., Deviprasad G.R., and Kutner W. J. Phys. Chem. A 104 (2000) 6887
19. P.A. Karr, M.E. Zandler, F. D'Souza, to be published.
20. D'Souza F., Zandler M.E., Smith P.M., Deviprasad G.R., Arkady K., Fujitsuka M., and Ito O. J. Phys. Chem. A 106 (2002) 649
21. Zandler M.E., Smith P.M., Fujitsuka M., Ito O., and D'Souza F. J. Org. Chem. 67 (2002) 9122
22. G.R. Deviprasad, P.M. Smith, M.E. Zandler, L.M. Rogers, F. D'Souza, Photosynth. Res. (2005) (in press).
23. Marczak R., Hoang V.T., Noworyta K., Zandler M.E., Kutner W., and D'Souza F. J. Mater. Chem. 12 (2002) 2123
24. D'Souza F., Zandler M.E., Gadde S., Hoang V.T., Marczak R., Noworyta K., and Kutner W. Proc. Electrochem. Soc. 12 (2002) 1
25. Sponer J., and Hobza P. J. Phys. Chem. A 104 (2000) 4592
26. D'Souza F., Deviprasad G.R., Zandler M.E., Hoang V.T., Arkady K., VanStipdonk M., Perera A., El-Khouly M.E., Fujitsuka M., and Ito O. J. Phys. Chem. A 106 (2002) 3243
27. D'Souza F., Deviprasad G.R., Rahman M.S., and Choi J.-P. Inorg. Chem. 38 (1999) 2157
28. El-Khouly M.E., Rogers L.M., Zandler M.E., Gadde S., Fujitsuka S.M., Ito O., and D'Souza F. Chem. Phys. Chem. 4 (2003) 474
29. D'Souza F., El-Khouly M.E., Gadde S., McCarty A.L., Karr P.A., Zandler M.E., Araki Y., and Ito O. J. Phys. Chem. 109 (2005) 10107
30. D'Souza F., Rath N.P., Deviprasad G.R., and Zandler M.E. Chem. Commun. (2001) 267
31. S. Gadde, D.R. Powell, M.E. Zandler, F. D'Souza, J. Porphyrins Phthalocyanines (in press).
32. Tsuzuki S., and Luthi H.P. J. Chem. Phys. 114 (2001) 3949
33. Wang Y., and Lin Z. J. Am. Chem. Soc. 125 (2003) 6072
34. Tran F., Weber J., and Wesolowski T.A. Helv. Chim. Acta 84 (2001) 1489
35. Reyes A., Tlenkopatchev M.A., Fomina L., Guadarrama P., and Fomine S. J. Phys. Chem. 107 (2003) 7027
36. D'Souza F., Gadde S., Zandler M.E., Itou M., Araki Y., and Ito O. Chem. Comm. (2004) 2276
37. El-Khouly M.E., Gadde S., Deviprasad G.R., Fujitsuka M., and Ito O. J. Porphyrins Phthalocyanines 7 (2003) 1
38. F. D'Souza, S. Gadde, M.E. Zandler, M.E. El-Khouly, Y. Araki, O. Ito, J. Porphyrins Phthalocyanines (in press).
39. D'Souza F., Smith P.M., Gadde S., McCarty A.L., Kullman M., Zandler M.E., Itou M., Yasuyaki A., and Ito O. J. Phys. Chem. B 108 (2004) 11333
40. D'Souza F., Smith P.M., Zandler M.E., McCarty A.L., Itou M., Araki Y., and Ito O. J. Am. Chem. Soc. 126 (2004) 7898
41. D'Souza F., Deviprasad G.R., Zandler M.E., El-Khouly M.E., Fujitsuka M., and Ito O. J. Phys. Chem. A 107 (2003) 4801
42. D'Souza F., El-Khouly M.E., Gadde S., Zandler M.E., McCarty A.L., Araki Y., and Ito O. Tetrahedron 62 (2006) 1967
43. D'Souza F., Chitta R., Gadde S., Zandler M.E., Sandanayaka A.S.D., Araki Y., and Ito O. Chem. Commun. 10 (2005) 1279
44. D'Souza F., Chitta R., Gadde S., Zandler M.E., McCarty A.L., Atula A.S.D., Araki Y., and Ito O. Chem. Eur. J. 11 (2005) 4416
45. Shephard M.J., and Paddon-Row M.N. J. Porphyrins and Phthalocyanines 6 (2002) 783
46. D'Souza F., Gadde S., Zandler M.E., Arkady K., El-Khouly M.E., Fujitsuka M., and Ito O. J. Phys. Chem. A 106 (2002) 12393
47. El-Khouly M.E., Araki Y., Ito O., Gadde S., McCarty A.L., Karr P.A., Zandler M.E., and D'Souza F. Phys. Chem. Chem. Phys. 7 (2005) 3163
48. Basiuk V.A. J. Phys. Chem. A 109 (2005) 3704
49. Yamaguchi Y. J. Chem. Phys. 120 (2004) 7963
50. Tappura K., Cramariuc O., Hukka T.I., and Rantala T.T. Phys. Chem. Chem. Phys. 7 (2005) 3126
51. Schuster D.I., Jarowski P.D., Kirschner A.N., and Wilson S.R. J. Mater. Chem. 12 (2002) 2041
52. Jarowski P.D., Schuster D.I., and Wilson S.R. Proc. Electrochem. Soc. 12 (2002) 106
53. Wilson S.R., MacMahon S., Tat F.T., Jarowski P.D., and Schuster D.I. Chem. Commun. 2 (2003) 226
54. Parusel A.B.J. J. Photochem. Photobiol. B: Biology 55 (2000) 188
55. Armaroli N., Diederich F., Echegoyen L., Habicher T., Flamigni L., Marconi G., and Nierengarten J.-F. New J. Chem. 23 (1999) 77
56. Sun Y., Drovetskaya T., Bolskar R.D., Bau R., Boyd P.E., and Reed C.A. J. Org. Chem. 62 (1997) 3642
57. Liu X.-J., Feng J.-K., Ren A.-M., and Zhou X. THEOCHEM 635 (2003) 191
58. Guldi D.M. Chem. Soc. Rev. 31 (2002) 22
59. Sun D., Tham F.S., Reed C.A., Chaker L., and Boyd P.D.W. J. Am. Chem. Soc. 124 (2002) 6604
60. Fukuzumi S., Ohkubo K., Imahori H., Shao J., Ou Z., Zheng G., Chem Y., Pandey R.K., Fujitsuka M., Ito O., and Kadish K.M. J. Am. Chem. Soc. 123 (2001) 10676
61. Chukharev V., Tkachenko N.V., Efimov A., Guldi D.M., Hirsch A., Scheloske M., and Lemmetyinen H. J. Phys. Chem. B 108 (2004) 16377
62. Loutfy R.O., and Loutfy R.O. Can. J. Chem. 54 (1976) 1454
63. Stowasser R., and Hoffmann R. J. Am. Chem. Soc. 121 (1999) 3414
64. Cramer C.J. Essentials of Computational Chemistry (2002), Wiley, Chichester, UK 252-255
65. Chang D.P., Gritsenko O.V., and Baerends E.J. J. Chem. Phys. 116 (2002) 1760
66. Zhan C.-G., Nichols J.A., and Dixon D.A. J. Phys. Chem. A 107 (2003) 4184