Gating the mechanistic pathway to the elusive 4-membered ring azeteoporphyrin

Journal of the American Chemical Society

Volumn 133, Issue 33, 2011, Pages 13110-13120

  Dye, David F ^a   Köpke, Tillmann ^a   Ramabhadran, Raghunath O ^a   Raghavachari, Krishnan ^a   Zaleski, Jeffrey M ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BOND INSERTION; CARBENES; COMPUTATIONAL MODELING; ELECTRONIC ABSORPTION SPECTRA; ELECTRONIC CONFIGURATION; ELECTRONIC TRANSITION; FREE BASE; GEOMETRIC CONSTRAINT; INTRAMOLECULAR REACTIVITY; LASER PHOTOLYSIS; LOW TEMPERATURES; MATRIX; MECHANISTIC PATHWAYS; ORBITAL SYMMETRIES; OUT-OF-PLANE; PHENYL GROUP; PHOTOINTERMEDIATES; PHOTOPRODUCTS; REACTION PROFILE; ROOM TEMPERATURE; SHARP CONTRAST; WOLFF REARRANGEMENT;

ABSORPTION; ABSORPTION SPECTROSCOPY; PHOTOLYSIS; RAMAN SPECTROSCOPY; REACTION INTERMEDIATES; TOLUENE;

ORGANIC COMPOUNDS;

AZETEOPORPHYRIN; BUTANOL; CARBENE; COPPER; KETENE DERIVATIVE; NICKEL; PORPHYRIN DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; BIOTRANSFORMATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; GEOMETRY; MASS SPECTROMETRY; MOLECULAR ELECTRONICS; MOLECULAR MECHANICS; MOLECULAR MODEL; OPTICAL DENSITY; PHOTOCHEMISTRY; PHOTOLYSIS; RAMAN SPECTROMETRY; ROOM TEMPERATURE; SIMULATION; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY; WOLFF REARRANGEMENT;

EID: 80051775089     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja203451k     Document Type: Article

References (66)

1. Dougherty, T. J.; Gomer, C. J.; Henderson, B. W.; Jori, G.; Kessel, D.; Korbelik, M.; Moan, J.; Peng, Q. J. Natl. Cancer Inst. 1998, 90, 889
2. Hagiya, Y.; Adachi, T.; Ogura, S.-I.; An, R.; Tamura, A.; Nakagawa, H.; Okura, I.; Mochizuki, T.; Ishikawa, T. J. Exp. Ther. Oncol. 2008, 7, 153
3. Josefsen, L. B.; Boyle, R. W. Met.-Based Drugs 2008, 2008, 276109
4. Juarranz, A.; Jaen, P.; Sanz-Rodriguez, F.; Cuevas, J.; Gonzalez, S. Clin. Transl. Oncol. 2008, 10, 148
5. Karotki, A.; Khurana, M.; Lepock, J. R.; Wilson, B. C. Photochem. Photobiol. 2006, 82, 443
6. Silva, J. N.; Filipe, P.; Morliere, P.; Maziere, J.-C.; Freitas, J. P.; Cirne De Castro, J. L.; Santus, R. Bio-Med. Mater. Eng. 2006, 16, S147
7. Szurko, A.; Kraemer-Marek, G.; Widel, M.; Ratuszna, A.; Habdas, J.; Kus, P. Acta Biochim. Pol. 2003, 50, 1165
8. Wu, L.; Yang, L.; Huang, J.; Zhang, L.; Weng, X.; Zhang, X.; Shen, C.; Zhou, X.; Zheng, C. Chem. Biodiversity 2009, 6, 1066
9. Ambroise, A.; Wagner, R. W.; Rao, P. D.; Riggs, J. A.; Hascoat, P.; Diers, J. R.; Seth, J.; Lammi, R. K.; Bocian, D. F.; Holten, D.; Lindsey, J. S. Chem. Mater. 2001, 13, 1023
10. Bernini, R.; Tonezzer, M.; Mottola, F.; Zeni, L.; Quaranta, A.; Maggioni, G.; Carturan, S.; Mea, G. Sens. Actuators, B 2007, 127, 231
11. Cho, Y.-J.; Ahn, T. K.; Song, H.; Kim, K. S.; Lee, C. Y.; Seo, W. S.; Lee, K.; Kim, S. K.; Kim, D.; Park, J. T. J. Am. Chem. Soc. 2005, 127, 2380
12. Di Natale, C.; Salimbeni, D.; Paolesse, R.; Macagnano, A.; D'Amico, A. Sens. Actuators, B 2000, 65, 220
13. He, X.; Liu, H.; Li, Y.; Liu, Y.; Lu, F.; Li, Y.; Zhu, D. Macromol. Chem. Phys. 2005, 206, 2199
14. Jang, J. H.; Jeon, K.-S.; Oh, S.; Kim, H.-J.; Asahi, T.; Masuhara, H.; Yoon, M. Chem. Mater. 2007, 19, 1984
15. Liu, C.-y.; Bard, A. J. Acc. Chem. Res. 1999, 32, 235
16. Liu, C.-y.; Tang, H.; Bard, A. J. J. Phys. Chem. 1996, 100, 3587
17. Sgobba, V.; Giancane, G.; Conoci, S.; Casilli, S.; Ricciardi, G.; Guldi, D. M.; Prato, M.; Valli, L. J. Am. Chem. Soc. 2007, 129, 3148
18. Amao, Y.; Komori, T. Langmuir 2003, 19, 8872
19. Campbell, W. M.; Jolley, K. W.; Wagner, P.; Wagner, K.; Walsh, P. J.; Gordon, K. C.; Schmidt-Mende, L.; Nazeeruddin, M. K.; Wang, Q.; Gratzel, M.; Officer, D. L. J. Phys. Chem. C 2007, 111, 11760
20. Cheng, Y.-J.; Yang, S.-H.; Hsu, C.-S. Chem. Rev. 2009, 109, 5868
21. Cherian, S.; Wamser, C. C. J. Phys. Chem. B 2000, 104, 3624
22. Hasselman, G. M.; Watson, D. F.; Stromberg, J. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S.; Meyer, G. J. J. Phys. Chem. B 2006, 110, 25430
23. Jasieniak, J.; Johnston, M.; Waclawik, E. R. J. Phys. Chem. B 2004, 108, 12962
24. Kay, A.; Graetzel, M. J. Phys. Chem. 1993, 97, 6272
25. Kim, H.-S.; Kim, C.-H.; Ha, C.-S.; Lee, J.-K. Synth. Met. 2001, 117, 289
26. Nocera, D. G. Inorg. Chem. 2009, 48, 10001
27. Takahashi, K.; Takano, Y.; Yamaguchi, T.; Nakamura, J.-i.; Yokoe, C.; Murata, K. Synth. Met. 2005, 155, 51
28. Hasobe, T.; Fukuzumi, S.; Kamat, P. V. J. Phys. Chem. B 2006, 110, 25477
29. Huang, X.; Zhu, C.; Zhang, S.; Li, W.; Guo, Y.; Zhan, X.; Liu, Y.; Bo, Z. Macromolecules 2008, 41, 6895
30. Imahori, H.; Kang, S.; Hayashi, H.; Haruta, M.; Kurata, H.; Isoda, S.; Canton, S. E.; Infahsaeng, Y.; Kathiravan, A.; Pascher, T. R.; Chábera, P.; Yartsev, A. P.; Sundström, V. J. Phys. Chem. A 2011, 115, 3679.
31. Kira, A.; Umeyama, T.; Matano, Y.; Yoshida, K.; Isoda, S.; Park, J. K.; Kim, D.; Imahori, H. J. Am. Chem. Soc. 2009, 131, 3198
32. Kongkanand, A.; Domínguez, R. M.; Kamat, P. V. Nano Lett. 2007, 7, 676
33. Lin, Y.-Y.; Chu, T.-H.; Li, S.-S.; Chuang, C.-H.; Chang, C.-H.; Su, W.-F.; Chang, C.-P.; Chu, M.-W.; Chen, C.-W. J. Am. Chem. Soc. 2009, 131, 3644
34. Loi, M. A.; Denk, P.; Hoppe, H.; Neugebauer, H.; Winder, C.; Meissner, D.; Brabec, C.; Sariciftci, N. S.; Gouloumis, A.; Vázquez, P.; Torres, T. J. Mater. Chem. 2003, 13, 700
35. Said, A. J.; Poize, G.; Martini, C.; Ferry, D.; Marine, W.; Giorgio, S.; Fages, F.; Hocq, J.; Bouclé, J.; Nelson, J.; Durrant, J. R.; Ackermann, J. J. Phys. Chem. C 2010, 114, 11273
36. Takahashi, K.; Iwanaga, T.; Yamaguchi, T.; Tomura, T.; Murata, K. Synth. Met. 2001, 123, 91
37. Takechi, K.; Shiga, T.; Akiyama, T.; Yamada, S. Appl. Phys. Express 2010, 3, 122301
38. Chandra, T.; Kraft, B. J.; Huffman, J. C.; Zaleski, J. M. Inorg. Chem. 2003, 42, 5158
39. Nath, M.; Huffman, J. C.; Zaleski, J. M. J. Am. Chem. Soc. 2003, 125, 11484
40. Nath, M.; Huffman, J. C.; Zaleski, J. M. J. Chem. Soc., Chem. Commun. 2003, 858
41. Nath, M.; Pink, M.; Zaleski, J. M. J. Am. Chem. Soc. 2005, 127, 478
42. Spence, J. D.; Cline, E. D.; LLagostera, D. M.; O'Toole, P. S. J. Chem. Soc., Chem. Commun. 2004, 180
43. Spence, J. D.; Hargrove, A. E.; Crampton, H. L.; Thomas, D. W. Tetrahedron Lett. 2007, 48, 725
44. Fouad, F. S.; Crasto, C. F.; Lin, Y.; Jones, G. B. Tetrahedron Lett. 2004, 45, 7753
45. Aihara, H.; Jaquinod, L.; Nurco, D. J.; Smith, K. M. Angew. Chem., Int. Ed. 2001, 40, 3439
46. Köpke, T.; Pink, M.; Zaleski, J. Synlett 2006, 2006, 2183
47. Köpke, T.; Pink, M.; Zaleski, J. Synlett 2008, 2008, 1882
48. Köpke, T.; Pink, M.; Zaleski, J. M. J. Chem. Soc., Chem. Commun. 2006, 1, 4940
49. Köpke, T.; Pink, M.; Zaleski, J. M. Org. Biomol. Chem. 2006, 4, 4059
50. Köpke, T.; Pink, M.; Zaleski, J. M. J. Am. Chem. Soc. 2008, 130, 15864
51. Kirmse, W. Eur. J. Org. Chem. 2002, 2002, 2193
52. McMahon, R. J.; Chapman, O. L.; Hayes, R. A.; Hess, T. C.; Krimmer, H. P. J. Am. Chem. Soc. 1985, 107, 7597
53. Wang, J.-L.; Toscano, J. P.; Platz, M. S.; Nikolaev, V.; Popik, V. J. Am. Chem. Soc. 1995, 117, 5477
54. Toscano, J. P.; Platz, M. S.; Nikolaev, V.; Popic, V. J. Am. Chem. Soc. 1994, 116, 8146
55. Burdzinski, G. T.; Wang, J.; Gustafson, T. L.; Platz, M. S. J. Am. Chem. Soc. 2008, 130, 3746
56. Burdzinski, G.; Réhault, J.; Wang, J.; Platz, M. S. J. Phys. Chem. A 2008, 112, 10108
57. Wang, J.; Burdzinski, G.; Kubicki, J.; Gustafson, T. L.; Platz, M. S. J. Am. Chem. Soc. 2008, 130, 5418
58. Burdzinski, G.; Platz, M. S. J. Phys. Org. Chem. 2010, 23, 308
59. Popik, V. V. Can. J. Chem. 2005, 83, 1382
60. Foresman, J. B.; Frisch, E. Exploring Chemistry With Electronic Structure Methods; Gaussian, Inc.: Pittsburgh, PA, 1996.
61. Gouterman, M. J. Mol. Spectrosc. 1961, 6, 138
62. Gouterman, M.; Wagniere, G.; Snyder, L. J. Mol. Spectrosc. 1963, 11, 108
63. Baerends, E. Coord. Chem. Rev. 2002, 230, 5
64. Chen, D.-M.; Liu, X.; He, T.-J.; Liu, F.-C. Chem. Phys. 2003, 289, 397
65. Venkataramanan, N. S.; Suvitha, A.; Nejo, H.; Mizuseki, H.; Kawazoe, Y. Int. J. Quantum Chem. 2011, 111, 2340.
66. Burdzinski, G. T.; Middleton, C. T.; Gustafson, T. L.; Platz, M. S. J. Am. Chem. Soc. 2006, 128, 14804