Androgynous porphyrins. Silver(II) quinoxalinoporphyrins act as both good electron donors and acceptors

Journal of the American Chemical Society

Volumn 130, Issue 29, 2008, Pages 9451-9458

  Fukuzumi, Shunichi ^a   Ohkubo, Kei ^a   Zhu, Weihua ^b   Sintic, Maxine ^c   Khoury, Tony ^c   Sintic, Paul J ^c   Wenbo, E ^b   Ou, Zhongping ^b   Crossley, Maxwell J ^c   Kadish, Karl M ^b  

^a OSAKA UNIVERSITY   (Japan)

^b University of Houston   (United States)

^c UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ARSENIC COMPOUNDS; CHEMICAL OXYGEN DEMAND; ELECTROCHEMICAL OXIDATION; ELECTROLYSIS; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRONS; METALLIZING; METALS; NEGATIVE IONS; OXIDATION; PARAMAGNETIC RESONANCE; PORPHYRINS; POSITIVE IONS; REDUCTION; SILVER COMPOUNDS; SPECTROELECTROCHEMISTRY; SULFUR COMPOUNDS;

AMERICAN CHEMICAL SOCIETY (ACS); DFT CALCULATIONS; ELECTRODE REACTIONS; ELECTRON ACCEPTORS; ELECTRON DONORS; ELECTRON PARAMAGNETIC RESONANCE (EPR) SPECTROSCOPY; ELECTRON TRANSFER (ET); HOMO-LUMO GAP (HLG); MACROCYCLE; METAL CENTERS; METAL OXIDATION; METALLOPORPHYRIN COMPLEXES; NON AQUEOUS MEDIUM; ONE ELECTRON OXIDATIONS; ONE ELECTRON REDUCTIONS; OXIDATION POTENTIALS; PORPHYRIN MACROCYCLE; POTENTIAL SHIFTS; QUINOXALINE (QX); RADICAL ANIONS; RADICAL CATION (RC); REDUCTION POTENTIALS; TETRAKIS; UV VIS SPECTROELECTROCHEMISTRY;

SILVER;

ANION; MACROCYCLIC COMPOUND; METALLOPORPHYRIN; PORPHYRIN DERIVATIVE; QUINOXALINOPORPHYRIN; RADICAL; SILVER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; MOLECULAR STABILITY; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROELECTROCHEMISTRY;

EID: 47749126233     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja801318b     Document Type: Article

References (53)

1. Fukuzumi, S. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 8, pp 115-152.
2. Kadish, K. M.; Van Caemelbecke, E.; Royal, G. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 8; pp 1-114.
3. (a) Wasielewski, M. R. Chem. Rev. 1992, 92, 435.
4. (b) Wasielewski, M. R.; Wiederrecht, G. P.; Svec, W. A.; Niemczyk, M. P. Sol. Energy Mater. Sol. Cells 1995, 38, 127.
5. (a) Gust, D.; Moore, T. A. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 8, pp 153-190.
6. (b) Gust, D.; Moore T. A.; Moore, A. L. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 3, pp 272-336.
7. Fukuzumi, S.; Imahori, H. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 927-975.
8. Fukuzumi, S.; Guldi, D. M. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 270-337.
9. Kadish, K. M.; E, W.; Ou, Z.; Shao, J.; Sintic, P. J.; Ohkubo, K.; Fukuzumi, S.; Crossley, M. J. Chem. Soc., Chem. Commun. 2002, 356.
10. Ou, Z.; Kadish, K. M.; E, W.; Shao, J.; Sintic, P. J.; Ohkubo, K.; Fukuzumi, S.; Crossley, M. J. Inorg. Chem. 2004, 43, 2078.
11. Harriman, A.; Sauvage, J.-P. Chem. Soc. Rev. 1996, 25, 41.
12. (a) Chambron, J. C.; Chardon-Noblat, S.; Harriman, A.; Heitz, V.; Sauvage, J. P. Pure Appl. Chem. 1993, 65, 2343.
13. (b) Chambron, J.-C.; Collin, J.-P.; Dalbavie, J.-O.; Dietrich-Buchecker, C. O.; Heitz, V.; Odobel, F.; Solladie, N.; Sauvage, J.-P. Coord. Chem. Rev. 1998, 178-180, 1299.
14. Blanco, M.-J.; Consuelo Jiménez, M.; Chambron, J.-C.; Heitz, V.; Linke, M.; Sauvage, J.-P. Chem. Soc. Rev. 1999, 28, 293.
15. Flamigni, L.; Barigelletti, F.; Armaroli, N.; Collin, J.-P.; Dixon, I. M.; Sauvage, J.-P.; Williams, J. A. G. Coord. Chem. Rev. 1999, 190-192, 671.
16. Fukuzumi, S.; Ohkubo, K.; E, W.; Ou, Z.; Shao, J.; Kadish, K. M.; Hutchison, J. A.; Ghiggino, K. P.; Sintic, P. J.; Crossley, M. J. J. Am. Chem. Soc. 2003, 125, 14984.
17. Ohkubo, K.; Sintic, P. J.; Tkachenko, N. V.; Lemmetyinen, H.; E, W.; Ou, Z.; Shao, J.; Kadish, K. M.; Crossley, M. J.; Fukuzumi, S. Chem. Phys. 2006, 326, 3.
18. Godziela, G. M.; Goff, H. M. J. Am. Chem. Soc. 1986, 108, 2237.
19. Kadish, K. M.; Davis, D. G.; Furhop, J.-H. Angew. Chem., Int. Ed. Engl. 1972, 11, 1014.
20. Fuhrhop, J.-H.; Kadish, K. M.; Davis, D. G. J. Am. Chem. Soc. 1973, 95, 5140.
21. Antipas, A.; Dolphin, D.; Gouterman, M.; Johnson, E. C. J. Am. Chem. Soc. 1978, 100, 7705.
22. Karweik, D.; Wigograd, N.; Davis, D. G.; Kadish, K. M. J. Am. Chem. Soc. 1974, 96, 591.
23. Scheidt, W. R.; Mondal, J. U.; Eigenbrot, C. W.; Adler, A.; Radonovich, L. J.; Hoard, J. L. Inorg. Chem. 1986, 25, 795.
24. For Ag(III) complexes of corroles, see: Brückner, C.; Barta, C. A.; Brinas, R. P.; Krause Bauer, J. A. Inorg. Chem. 2003, 42, 1673.
25. For Ag(III) complexes of carbaporphyrins and N-confused porphyrins, see: (a) Furuta, H.; Ogawa, T.; Uwatoko, Y.; Araki, K. Inorg. Chem. 1999, 38, 2676.
26. (b) Muckey, M. A.; Szczepura, L. F.; Ferrence, G. M.; Lash, T. D. Inorg. Chem. 2002, 41, 4840.
27. Wolberg, A.; Manassen, J. J. Am. Chem. Soc. 1970, 92, 2982.
28. Fuhrhop, J.-H. Struct. Bonding 1974, 18, 1.
29. Scholz, W. F.; Reed, C. A.; Lee, J. L.; Scheidt, W. R.; Lang, G. J. Am. Chem. Soc. 1982, 104, 6791.
30. Konishi, S.; Hoshino, M.; Imamura, M. J. Am. Chem. Soc. 1982, 104, 2057.
31. For singly oxidized copper(II) phthalocyanine, see: Gardberg, A. S.; Doan, P. E.; Hoffman, B. M.; Ibers, J. A. Angew. Chem., Int. Ed. 2001, 40, 244.
32. Erler, B. S.; Scholz, W. F.; Lee, Y. J.; Scheidt, W. R.; Reed, C. A. J. Am. Chem. Soc. 1987, 109, 2644.
33. Kadish, K. M.; Lin, X. Q.; Ding, J. Q.; Wu, Y. T.; Araullo, C. Inorg. Chem. 1986, 25, 3236.
34. Kadish, K. M.; E, W.; Sintic, P. J.; Ou, Z.; Shao, J.; Ohkubo, K.; Fukuzumi, S.; Govenlock, L. J.; McDonald, J. A.; Try, A. C.; Cai, Z.-L.; Reimers, J. R.; Crossley, M. J. J. Phys. Chem. B 2007, 111, 8762.
35. E, W.; Kadish, K. M.; Sintic, P. J.; Khoury, T.; Govenlock, L. J.; Ou, Z.; Shao, J.; Ohkubo, K.; Reimers, J. R.; Fukuzumi, S.; Crossley, M. J. J. Phys. Chem. A 2008, 112, 556.
36. Fukuzumi, S.; Nakanishi, I.; Tanaka, K.; Suenobu, T.; Tabard, A.; Guilard, R.; Van Caemelbecke, E.; Kadish, K. M. J. Am. Chem. Soc. 1999, 121, 785.
37. Lin, X. Q.; Kadish, K. M. Anal. Chem. 1985, 1489.
38. Crossley, M. J.; Sintic, P. J.; Walton, R.; Reimers, J. R. Org. Biomol. Chem. 2003, 1, 2777-2787.
39. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
40. Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004. For full list of authors, see Supporting Information S9.
41. Dennington, R., II; Keith, T.; Millam, J.; Eppinnett, K.; Hovell, W. L.; Gilliland, R. Gaussview; Semichem: Shawnee Mission, KS, 2003.
42. Kneubühl, F. K.; Koski, W. S.; Caughey, W. S. J. Am. Chem. Soc. 1961, 83, 1607.
43. MacCragh, A.; Storm, C. B.; Koski, W. S. J. Am. Chem. Soc. 1965, 87, 1470.
44. Brown, T. G.; Hoffman, B. M. Mol. Phys. 1980, 39, 1073.
45. 44 For photoinduced demetalation of (TPP)Ag under reducing conditions, see: Kunkely, H.; Vogler, A. Inorg. Chem. Commun. 2007, 10, 479.
46. Giraudeau, A.; Louati, A.; Callot, H. J.; Gross, M. Inorg. Chem. 1981, 20, 769.
47. (a) Ou, Z.; E, W.; Shao, J.; Burn, P. L.; Sheehan, C. S.; Walton, R.; Kadish, K. M.; Crossley, M. J. J. Porphyrins Phthalocyanines 2005, 9, 142.
48. (b) Sintic, P. J.; E, W.; Ou, Z.; Shao, J.; McDonald, J. A.; Cai, Z.; Kadish, K. M.; Crossley, M. J.; Reimers, J. R. Phys. Chem. Chem. Phys. 2008, 10, 515.
49. (c) Ou, Z.; E, W.; Zhu, W.; Thordarson, P.; Sintic, P. J.; Crossley, M. J.; Kadish, K. M. Inorg, Chem. 2007, 46, 10840.
50. For the formation of a triplet in silver(II) porphyrins in the solid state, see: Marumoto, K.; Takahashi, H.; Tanaka, H.; Kuroda, S.; Ishii, T.; Kanehama, R.; Aizawa, N.; Yamashita, M. J. Phys.: Condens. Matter 2004, 16, 8753.
51. Imahori, H.; Tamaki, K.; Guldi, D. M.; Luo, C.; Fujitsuka, M.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 2607.
52. •+ allows the electron transfer to undergo completion.
53. Fukuzumi, S.; Nishizawa, N.; Tanaka, T. J. Org. Chem. 1984, 49, 3571.