Greatly enhanced intermolecular π-dimer formation of a porphyrin trimer radical trications through multiple πbonds

Chemistry - A European Journal

Volumn 17, Issue 12, 2011, Pages 3420-3428

  Takai, Atsuro ^a   Gros, Claude P ^b   Barbe, Jean Michel ^b   Fukuzumi, Shunichi ^a,c  

^a OSAKA UNIVERSITY   (Japan)

^b UNIVERSITÉ DE BOURGOGNE   (France)

^c Ewha Womans University   (South Korea)

Author keywords

dimerization; electron transfer; electronic structure; multiple bonds; pi interactions

Indexed keywords

BOND FORMATION; CHARGE DELOCALIZATION; CHARGE-RESONANCE BAND; DIMER FORMATION; ELECTRON OXIDATION; ELECTRON TRANSFER; FORMATION CONSTANTS; INITIAL OXIDATION; MULTIPLE BONDS; NIR REGIONS; ONE-ELECTRON OXIDATION; OXIDIZED STATE; PI INTERACTIONS; PORPHYRIN RINGS; RADICAL CATIONS; THERMODYNAMIC PARAMETER; TRIPHENYL AMINES;

DENSITY FUNCTIONAL THEORY; DIMERIZATION; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRON TRANSITIONS; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; FREE RADICAL REACTIONS; MONOMERS; OXIDATION; PORPHYRINS; POSITIVE IONS; SPECTROSCOPIC ANALYSIS;

DIMERS;

CATION; PORPHYRIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; ELECTRON; ELECTRON SPIN RESONANCE; OXIDATION REDUCTION REACTION; TEMPERATURE;

CATIONS; DIMERIZATION; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRONS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PORPHYRINS; TEMPERATURE;

EID: 79952426325     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002822     Document Type: Article

References (64)

1. R. V. Bensasson, E. J. Land, A. L. Moore, R. L. Crouch, G. Dirks, T. A. Moore, D. Gust, Nature 1981, 290, 329.
2. A. A. Pascal, Z. F. Liu, K. Broess, B. vanOort, H. vanAmerongen, C. Wang, P. Horton, B. Robert, W. R. Chang, A. Ruban, Nature 2005, 436, 134.
3. D. T. McQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 2000, 100, 2537
4. V. Coropceanu, J. Cornil, D. A. daSilva, Y. Olivier, R. Silbey, J.-L. Bredas, Chem. Rev. 2007, 107, 926.
5. C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525.
6. J. S. Park, E. Karnas, K. Ohkubo, P. Chen, K. M. Kadish, S. Fukuzumi, C. W. Bielawski, T. W. Hudnall, V. M. Lynch, J. L. Sessler, Science 2010, 329, 1324
7. N. Ise, Phys. Chem. Chem. Phys. 2010, 12, 10279.
8. A. Takai, C. P. Gros, J.-M. Barbe, R. Guilard, S. Fukuzumi, Chem. Eur. J. 2009, 15, 3110
9. A. Takai, M. Chkounda, A. Eggenspiller, C. P. Gros, M. Lachkar, J.-M. Barbe, S. Fukuzumi, J. Am. Chem. Soc. 2010, 132, 4477.
10. O. W. Howarth, G. K. Fraenkel, J. Am. Chem. Soc. 1966, 88, 4514
11. J. K. Kochi, R. Rathore, P. L. Magueres, J. Org. Chem. 2000, 65, 6826
12. S. Fukuzumi, Y. Endo, H. Imahori, J. Am. Chem. Soc. 2002, 124, 10974
13. J.-M. Lü, S. V. Rosokha, J. K. Kochi, J. Am. Chem. Soc. 2003, 125, 12161
14. S. Fukuzumi, H. Kotani, K. Ohkubo, Phys. Chem. Chem. Phys. 2008, 10, 5159
15. S. Fukuzumi, R. Hanazaki, H. Kotani, K. Ohkubo, J. Am. Chem. Soc. 2010, 132, 11002.
16. J. J. Novoa, P. Lafuente, R. E. DelSesto, J. S. Miller, Angew. Chem. 2001, 113, 2608
17. Angew. Chem. Int. Ed. 2001, 40, 2540
18. R. E. DelSesto, J. S. Miller, P. Lafuente, J. J. Novoa, Chem. Eur. J. 2002, 8, 4894
19. J. Yuasa, T. Suenobu, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 12090
20. J. Yuasa, S. Fukuzumi, J. Am. Chem. Soc. 2007, 129, 12912.
21. T. P. Treynor, S. S. Andrews, S. G. Boxer, J. Phys. Chem. B 2003, 107, 11230
22. P. Kanchanawong, M. G. Dahlbom, T. P. Treynor, J. R. Reimers, N. S. Hush, S. G. Boxer, J. Phys. Chem. B 2006, 110, 18688.
23. M. R. Wasielewski, W. A. Svec, B. T. Cope, J. Am. Chem. Soc. 1978, 100, 1961.
24. H. S. Song, R. D. Orosz, C. A. Reed, W. R. Scheidt, Inorg. Chem. 1990, 29, 4274
25. W. R. Scheidt, B. S. Cheng, K. J. Haller, A. Mislankar, A. D. Rae, K. V. Reddy, H. S. Song, R. D. Orosz, C. A. Reed, F. Cukiernik, J. C. Marchon, J. Am. Chem. Soc. 1993, 115, 1181
26. K. E. Brancato-Buentello, S. J. Kang, W. R. Scheidt, J. Am. Chem. Soc. 1997, 119, 2839.
27. K. M. Barkigia, M. W. Renner, J. Fajer, J. Phys. Chem. B 1997, 101, 8398.
28. D. A. Shultz, H. Lee, R. K. Kumar, K. P. Gwaltney, J. Org. Chem. 1999, 64, 9124
29. S. Fukuzumi, T. Hasobe, K. Ohkubo, M. J. Crossley, P. V. Kamat, H. Imahori, J. Porphyrins Phthalocyanines 2004, 8, 191
30. M. J. Crossley, P. J. Sintic, J. A. Hutchison, K. P. Ghiggino, Org. Biomol. Chem. 2005, 3, 852
31. G. Pognon, C. Boudon, K. J. Schenk, M. Bonin, B. Bach, J. Weiss, J. Am. Chem. Soc. 2006, 128, 3488
32. F. D′Souza, R. Chitta, S. Gadde, L. M. Rogers, P. A. Karr, M. E. Zandler, A. S. Sandanayaka, Y. Araki, O. Ito, Chem. Eur. J. 2007, 13, 916
33. F. D′Souza, E. Maligaspe, K. Ohkubo, M. E. Zandler, N. K. Subbaiyan, S. Fukuzumi, J. Am. Chem. Soc. 2009, 131, 8787.
34. T. M. Wilson, T. Hori, M. C. Yooo, N. Aratani, A. Osuka, D. Kim, M. R. Wasielewski, J. Am. Chem. Soc. 2010, 132, 1383.
35. A. Takai, C. P. Gros, J.-M. Barbe, S. Fukuzumi, Phys. Chem. Chem. Phys. 2010, 12, 12160.
36. M. J. Ahrens, R. F. Kelley, Z. E. X. Dance, M. R. Wasielewski, Phys. Chem. Chem. Phys. 2007, 9, 1469
37. A. deLaEscosura, M. V. Martinez-Diaz, D. M. Guldi, T. Torres, J. Am. Chem. Soc. 2006, 128, 4112
38. A. I. Oliva, B. Ventura, F. Würthner, A. Camara-Campos, C. A. Hunter, P. Ballester, L. Flamigni, Dalton Trans. 2009, 4023.
39. S. V. Rosokha, I. S. Neretin, D. Sun, J. K. Kochi, J. Am. Chem. Soc. 2006, 128, 9394.
40. F. D′Souza, S. Gadde, D. M. S. Islam, C. A. Wijesinghe, A. L. Schumacher, M. E. Zandler, Y. Araki, O. Ito, J. Phys. Chem. A 2007, 111, 8552
41. N. K. Subbaiyan, L. Obraztsov, C. A. Wijesinghe, K. Tran, W. Kutner, F. D′Souza, J. Phys. Chem. C 2009, 113, 8982.
42. K. M. Kadish, N. Guo, E. VanCaemelbecke, A. Froiio, R. Paolesse, D. Monti, P. Tagliatesta, T. Boschi, L. Prodi, F. Bolletta, N. Zaccheroni, Inorg. Chem. 1998, 37, 2358
43. D. Bellows, S. M. Aly, C. P. Gros, M. E. Ojaimi, J.-M. Barbe, R. Guilard, P. D. Harvey, Inorg. Chem. 2009, 48, 7613.
44. B. Franck, G. Krautstrunk, Liebigs Ann. Chem. 1993, 1069
45. S. Kawabata, I. Yamazaki, Y. Nishimura, Bull. Chem. Soc. Jpn. 1997, 70, 1125.
46. H. L. Anderson, Inorg. Chem. 1994, 33, 972
47. A. Satake, Y. Kobuke, Org. Biomol. Chem. 2007, 5, 1679
48. Z. J. Chen, A. Lohr, C. R. Saha-Moller, F. Würthner, Chem. Soc. Rev. 2009, 38, 564.
49. Other one-electron oxidants, such as tris(4-bromophenyl)ammoniumyl hexachloroantimonate, are also available.
50. J. H. Fuhrhop, P. Wasser, D. Riesner, D. Mauzerall, J. Am. Chem. Soc. 1972, 94, 7996.
51. C. Lambert, G. Noll, J. Am. Chem. Soc. 1999, 121, 8434.
52. It is difficult to detect the dimeric species by using either MALDI TOF or ESI mass spectrometry because they may easily decompose into the monomeric species in the gas phase.
53. E. T. Seo, R. F. Nelson, J. M. Fritsch, L. S. Marcoux, D. W. Leedy, R. N. Adams, J. Am. Chem. Soc. 1966, 88, 3498
54. K. Sreenath, C. V. Suneesh, V. K. Kumar, K. R. Gopidas, J. Org. Chem. 2008, 73, 3245.
55. 3 are three-electron processes (see FigureS6 in the Supporting Information for CV and DPV analysis).
56. 3 is strongly associated with the dimerization equilibrium under the present conditions.
57. Because porphyrin planes are not strictly flat nor parallel to each other, the plane distance exhibits distribution from 3.2 to 3.7Å.
58. C. R. Newman, C. D. Frisbie, D. A. da Silva, J. L. Bredas, P. C. Ewbank, K. R. Mann, Chem. Mater. 2004, 16, 4436
59. M. J. Tauber, R. F. Kelley, J. M. Giaimo, B. Rybtchinski, M. R. Wasielewski, J. Am. Chem. Soc. 2006, 128, 1782.
60. H. Segawa, Y. Senshu, J. Nakazaki, K. Susumu, J. Am. Chem. Soc. 2004, 126, 1354.
61. 1HNMR spectrum at low temperature, which exhibits only the signals in the diamagnetic region (FigureS9 in the Supporting Information).
62. R. E. Desimone, R. S. Drago, J. Am. Chem. Soc. 1970, 92, 2343.
63. C. K. Mann, K. K. Barnes, Electrochemical Reactions in Nonaqueous Systems, Marcel Dekker, New York, 1970.
64. Gaussian09, Revision A.02, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery,Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford CT, 2009.