A theoretical investigation on the spectroscopic properties and photosensitizing capability of 5, 10, 15, 20-tetraphenylsapphyrin and 5, 10, 15, 20-tetraphenyl-26,28-diheterosapphyrins with two O, S, or Se Atoms

Theoretical Chemistry Accounts

Volumn 127, Issue 5, 2010, Pages 475-484

  López, Ramón ^a   Menéndez, M Isabel ^a   Santander Nelli, Mireya ^b   Cárdenas Jirón, Gloria I ^b  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

Author keywords

Excited states; Heterosapphyrins; Photosensitizers; Sapphyrin; TD DFT; V UV spectra

Indexed keywords

EID: 78149412642     PISSN: 1432881X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00214-010-0735-5     Document Type: Article

References (78)

1. Dolphin D (1994) Can J Chem 72: 1005.
2. Wang Z, Lecane PS, Thiemann P, Fan Q, Cortez C, Ma X, Tonev D, Miles D, Naumovski L, Miller RA, Magda D, Cho DG, Sessler JL, Pike BL, Yeligar SM, Karaman MW, Hacia GJ (2007) Mol Cancer 6: 9.
3. Sessler JL, Davis JM (2001) Acc Chem Res 34: 989.
4. Sessler JL, Seidel D (2003) Angew Chem Int Ed 42: 5134.
5. Sessler JL, Tvemoes NA, Davis J, Anzenbacher P, Jursikova K Jr, Sato W, Seidel D, Lynch V, Black CB, Try A, Andrioletti B, Hemmi G, Mody TD, Magda DJ, Kral V (1999) Pure Appl Chem 71: 2009.
6. Boul PJ, Cho DG, Rahman GMA, Marquez M, Ou Z, Kadish KM, Guldi DM, Sessler JL (2007) J Am Chem Soc 129: 5683.
7. Steiner E, Fowler PW (2004) Org Biomol Chem 2: 34.
8. Sessler JL, Cho DG, Stepiens M, Lynch V, Waluk J, Yoon ZS, Kim D (2006) J Am Chem Soc 128: 12640.
9. Rezler EM, Seenisamy J, Bashyam S, Kim MY, White E, Wilson WD, Hurley LH (2005) J Am Chem Soc 127: 9439.
10. Panda PK, Kang YJ, Lee CH (2005) Angew Chem Int Ed 44: 4053.
11. Misra R, Chandrashekar TK (2008) Acc Chem Res 41: 265.
12. Pushpan SK, Chandrashekar TK (2002) Pure Appl Chem 74: 2045.
13. Chmielewski PJ, Latos-Grazynski L, Rachlewicz K (1995) Chem Eur J 1: 68.
14. Narayanan SJ, Sridevi B, Chandrashekar TK, Vij A, Roy R (1998) Angew Chem Int Ed 37: 3394.
15. Pushpan SK, Narayanan SJ, Srinivasan A, Mahajan S, Chandrashekar TK, Roy R (1998) Tetrahedron Lett 39: 9249.
16. Rachlewicz K, Sprutta N, Chmielewski PJ, Latos-Grazynski L (1998) J Chem Soc Perkin Trans 2: 969.
17. Brückner C, Sternberg ED, Boyle RW, Dolphin D (1997) Chem Commun 1689.
18. Szterenberg L, Latos-Grazynski L (1999) J Phys Chem A 103: 3302.
19. Szterenberg L, Latos-Grazynski L (1999) J Mol Struct (Theochem) 490: 33.
20. Cárdenas-Jirón GI, Venegas C, López R, Menéndez MI (2008) J Phys Chem A 112: 8100.
21. Rachlewicz K, Sprutta N, Latos-Grazynski L, Chmielewski PJ, Szterenberg L (1998) J Chem Soc Perkin Trans 2: 959.
22. Petit L, Quartarolo AD, Adamo C, Russo N (2006) J Phys Chem B 110: 2398.
23. Quartarolo AD, Russo N, Sicilia E, Lelj F (2007) J Chem Theory Comput 3: 860.
24. Sundholm D (2000) Phys Chem Chem Phys 2: 2275.
25. Shimizu Y, Shen Z, Okujima T, Uno H, Ono N (2004) Chem Commun 374.
26. Baker JD, Zerner MC (1990) Chem Phys Lett 175: 192.
27. Baraldi I, Carnevali A, Ponterini G, Vanossi D (1995) J Mol Struct (Theochem) 333: 121.
28. Bauernschmitt R, Ahlrichs R (1996) Chem Phys Lett 256: 454.
29. Foresman JB, Head-Gordon M, Pople JA, Frisch MJ (1992) J Phys Chem 96: 135.
30. Nagashima U, Takada T, Ohno K (1986) J Chem Phys 85: 4524.
31. Nooijen M, Barlett RJ (1997) J Chem Phys 106: 6449.
32. Parusel ABJ, Ghosh A (2000) J Phys Chem A 104: 2504.
33. Parusel ABJ, Grimme S (2001) J Phorphyrins Phthalocyanines 5: 225.
34. Yamamoto Y, Noro T, Ohno K (1992) Int J Quantum Chem 42: 1563.
35. Baerends EJ, Ricciardi G, Rosa A, van Gisbergen SJA (2002) Coord Chem Rev 230: 5.
36. Kitao O, Ushiyama H, Miura N (1999) J Chem Phys 110: 2936.
37. Merchán M, Ortí E, Roos BO (1994) Chem Phys Lett 226: 27.
38. Serrano-Andrés L, Merchán M, Rubio M, Roos BO (1998) Chem Phys Lett 295: 195.
39. Roos BO, Fülscher MP, Fülscher MP, Malmqvist PA, Merchán M, Serrano-Andrés L (1995) In: Langhoff SR (ed) Quantum mechanical electronic structure calculations with chemical accuracy. Kluwer, Dordrecht, p 357 357.
40. Grimme S, Waletzke M (1999) J Chem Phys 111: 5645.
41. van Gisbergen SJA, Rosa A, Ricciardi G, Baerends EJ (1999) J Chem Phys 111: 2499.
42. Gwaltney SR, Barlett RJ (1998) J Chem Phys 108: 6790.
43. Furche F, Ahlrich R (2002) J Chem Phys 117: 7433.
44. Stratmann RE, Scuseria GE, Frisch MJ (1998) J Chem Phys 109: 8218.
45. Gaussian 03, Revision E. 01, Frisch, MJ, Trucks GW; Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JAJr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA Gaussian, Inc., Wallingford CT, 2004.
46. Becke AD (1998) Phys Rev A 38: 3098.
47. Becke AD (1993) J Chem Phys 98: 5648.
48. Lee C, Yang W, Parr RG (1988) Phys Rev B 37: 785.
49. Hay PJ, Wadt WR (1985) J Chem Phys 82: 299.
50. Hehre WJ, Radom L, Radom L, Pople JA, Schleyer PvR (1986) Ab initio molecular orbital theory. Wiley, New York.
51. Jaguar 5. 5, Schrodinger Inc.: Portland, OR, 2004.
52. Liu X-J, Pan Q-J, Meng J, Feng J-K (2006) J Mol Struct (Theochem) 765: 61.
53. Petit L, Adamo C, Russo N (2005) J Phys Chem B 109: 12214.
54. Adamo C, Barone V (1999) J Chem Phys 110: 6158.
55. Ernzerhof M, Scuseria GE (1999) J Chem Phys 110: 5029.
56. Zhao Y, Truhlar DG (2004) J Phys Chem A 108: 6908.
57. Zhao Y, Truhlar DG (2005) J Chem Theory Comput 1: 415.
58. Staroverov VN, Scuseria GE, Tao J, Perdew JP (2003) J Chem Phys 119: 12129.
59. Zhao Y, Truhlar DG (2007) J Chem Theory Comput 3: 289.
60. Barone V, Cossi M (1998) J Phys Chem A 102: 1995.
61. Tomasi J, Mennucci B, Cammi R (2005) Chem Rev 105: 2999.
62. Tomasi J, Persico M (1994) Chem Rev 94: 2027.
63. Cossi M, Barone V (2001) J Chem Phys 115: 4708.
64. Improta R, Barone V, Santoro F (2007) Angew Chem Int Ed 46: 405.
65. Santoro F, Barone V, Gustavsson T, Improta R (2006) J Am Chem Soc 128: 16312.
66. Scalmani G, Frisch MJ, Mennucci B, Tomasi J, Cammi R, Barone V (2005) J Chem Phys 124: 94107.
67. Reed AE, Curtiss LA, Weinhold F (1988) Chem Rev 88: 899.
68. Zhao Y, Schultz NE, Truhlar DG (2005) J Chem Phys 123: 161103.
69. Zhao Y, Schultz NE, Truhlar DG (2006) J Chem Theory Comput 2: 364.
70. Zhao Y, Truhlar DG (2008) Acc Chem Res 41: 157.
71. Gouterman M (1959) J Chem Phys 30: 1139.
72. Gouterman M (1961) J Mol Spectrosc 6: 138.
73. Gouterman M (1965) J Mol Spectrosc 16: 415.
74. Gouterman M, Wagniere GH, Snyder LC (1963) J Mol Spectrosc 11: 108.
75. Gensch T, Viappiani C, Braslavsky SE (1999) J Am Chem Soc 121: 10573.
76. Wang Z, Lecane PS, Thiemann P, Fan Q, Cortez C, Ma X, Tonev D, Miles D, Naumovski L, Miller RA, Magda D, Cho DG, Sessler JL, Pike BL, Yeligar SM, Karaman MW, Hacia JG (2007) Mol Cancer 6: 1.
77. Cho DG, Plitt P, Kim SK, Lynch V, Hong SJ, Lee CH, Sessler JL (2008) J Am Chem Soc 130: 10502.
78. Zhang P, Steelant W, Kumar M, Scholfield M (2007) J Am Chem Soc 129: 4526.