meso-aryl-substituted subporphyrins: Synthesis, structures, and large substituent effects on their electronic properties

Journal of the American Chemical Society

Volumn 129, Issue 15, 2007, Pages 4747-4761

  Inokuma, Yasuhide ^a   Zin, Seok Yoon ^b   Kim, Dongho ^b   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; ACETIC ACID; CHROMOPHORES; CONDENSATION; ELECTRONIC PROPERTIES; OXIDATION; SOLVENTS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

CHLOROACETIC ACID; SUBPORPHYRINS; TRIPYRROLIC MACROCYCLES;

PORPHYRINS;

1,2 DICHLOROBENZENE; ALDEHYDE; CHLOROACETIC ACID; PORPHYRIN DERIVATIVE; PYRIDINE;

ABSORPTION SPECTROSCOPY; ARTICLE; ELECTROCHEMICAL ANALYSIS; FLUORESCENCE SPECTROSCOPY; OXIDATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 34247542507     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja069324z     Document Type: Article

References (73)

1. (a) Franck, B.; Nonn, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1795-1811.
2. (b) Jasat, A.; Dolphin, D. Chem. Rev. 1997, 97, 2267-2340.
3. (c) Sessler, J. L.; Gebauer, A.; S. J. Weghorn, S. J. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M., Guilard, R., Eds; Academic Press: San Diego, 1999; Vol. 2, pp 55-124.
4. (d) Lash, T. D. Angew. Chem., Int. Ed. 2000, 39, 1763-1767.
5. (e) Furuta, H.; Maeda, H.; Osuka, A. Chem. Commun. 2002, 1795-1804.
6. (f) Sessler, J. L. D. Seidel, D. Angew. Chem., Int. Ed. 2003, 42, 5134-5175.
7. (g) Ghosh, A. Angew. Chem., Int. Ed. 2004, 43, 1918-1931.
8. (h) Chadrashekar, T. K.; Venkatraman, S. Acc. Chem. Res. 2003, 36, 676-691.
9. (a) Sessler, J. L.; Cyr, M. J.; Lynch, V.; McGhee, E.; Ibers, J. A. J. Am. Chem. Soc. 1990, 112, 2810-2813.
10. (b) Sessler, J. L.; Weghorn, S. J.; Lynch, V.; Johnson, M. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1509-1512.
11. (c) Vogel, E.; Bring, M.; Fink, J.; Rosen, D.; Schmickler, H.; Lex, J.; Chan, K. W. K.; Wu, Y. D.; Platter, D. A.; Nendel, M.; Houk, K. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2511-2514.
12. (d) Bring, M.; Dietrich, H.-J.; Dörr, J.; Hohlneicher, G.; Lex, J.; Jux, N.; Pütz, C.; Roeb, M.; Schmickler, H.; Vogel, E. Angew. Chem., Int. Ed. 2000, 39, 1105-1108.
13. (e) Vogel, E.; Michels, M.; Zander, L.; Lex, J.; Tuzun, N. S. Houk, K. N. Angew. Chem., Int. Ed. 2003, 42, 2857-2862.
14. (f) Sestune, J.; Maeda, S. J. Am. Chem. Soc. 2000, 122, 12405-12406.
15. (g) Sprutta, N.; Latos-Grażyński, L. Chem. Eur. J. 2001, 7, 5099-5112.
16. (h) Hung, C. H.; Jong, J. P.; Ho, M. Y.; Lee, G. H.; Peng, S. M. Chem. Eur. J. 2002, 8, 4542-4548.
17. (i) Anand, V. G.; Pushpan, S. K.; Venkatraman, S.; Dey, A.; Chandrashekar, T. K.; Joshi, B. S.; Roy, R.; Teng, W.; Senge, K. R. J. Am. Chem. Soc. 2001, 123, 8620-8621.
18. (j) Krivokapic, A.; Cowley, A. R.; Anderson, H. L. J. Org. Chem. 2003, 68, 1089-1096.
19. (k) Xu, L.; Ferrence, G. M.; Lash, T. D. Org. Lett. 2006, 8, 5113-5116.
20. (a) Neves, M. G. P. M. S.; Martins, R. M.; Tomé, A. C.; Silvestre, A. J. D.; Silva, A. M. S.; Félix, V.; Drew, M. G. B.; Cavaleiro, J. A. S. Chem. Commun. 1999, 385-386.
21. (b) Shin, J. Y.; Furuta, H.; Yoza, K.; Igarashi, S.; Osuka, A. J. Am. Chem. Soc. 2001, 123, 7190-7191.
22. (c) Suzuki, M.; Osuka, A. Org. Lett. 2003, 5, 3943-3946.
23. (d) Shimizu, S.; Shin, J. Y.; Furuta, H.; Ismael, R.; Osuka, A. Angew. Chem., Int. Ed. 2003, 42, 78-82.
24. (e) Shimizu, S.; Aratani, N.; Osuka, A. Chem. Eur. J. 2006, 12, 4909-4918.
25. (a) Paolesse, R. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 1999; Vol. 2, pp 201-232.
26. (b) Erbem, C.; Will, S.; Kadish, K. M. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 1999; Vol. 2, pp 233-300.
27. (a) Bloor, J. E.; Schlabitz, J.; Walden, C. C.; Demerdac, A. Can. J. Chem. 1964, 42, 2201.
28. (b) Marks, T. J.; Stojakovic, D. R. J. Am. Chem. Soc. 1978, 100, 1695-1705.
29. (c) Day, V. W.; Marks, T. J.; Wachter, W. A. J. Am. Chem. Soc. 1975, 97, 4519-4527.
30. Meller, A.; Ossko, A. Monatsh. Chem. 1972, 103, 150-155.
31. Claessens, C. G.; Gonzalez-Rodriguez, D.; Torres, T. Chem. Rev. 2002, 102, 835-853.
32. (a) González-Rodríguez, D.; Torres, T.; Guldi, D. M.; Rivera, J.; Echegoyen, L. Org. Lett. 2002, 4, 335-338.
33. (b) González-Rodríguez, D.; Torres, T.; Guldi, D. M.; Rivera, J.; Herranz, M. A.; Echegoyen, L. J. Am. Chem. Soc. 2004, 126, 6301-6313.
34. (a) Ros-Lis, J. V.; Martínez-Máñez, R.; Soto, J. Chem. Commun. 2005, 5260-5262.
35. (b) Xu, S.; Chen, K.; Tian, H. J. Mater. Chem. 2005, 15, 2676-2680.
36. (a) Sastre, A.; Torres, T.; Díaz-García, M. A.; Agulló-López, F.; Dhenaut, C.; Brasselet, S.; Ledoux, I.; Zyss, J. J. Am. Chem. Soc. 1996, 118, 2746-2747.
37. (b) Rojo, G.; Hierro, A.; Díaz-Garcia, M. A.; Agulló-Lopez, F.; del Ray, B.; Sastre, A.; Torres, T. Appl. Phys. Lett. 1997, 70, 1802-1804.
38. Claessens, C. G.; Torres, T. J. Am. Chem. Soc. 2002, 124, 14522-14523.
39. (a) Rodríguez-Morgade, M. S.; Esperanza, S.; Torres, T.; Barberá, J. Chem. Eur. J. 2005, 11, 354-360.
40. (b) Rauschnabel, J.; Hanack, M. Tetrahedron Lett. 1995, 36, 1629-1632.
41. (a) Kobayashi, N.; Kondo, R.; Nakajima, S.; Osa, T. J. Am. Chem. Soc. 1990, 112, 9640-9641.
42. (b) Sastre, A.; Torres, T.; Hanack, M. Tetrahedron Lett. 1995, 36, 8501-8504.
43. Kobayashi, N.; Takeuchi, Y.; Matsuda, A. Angew. Chem., Int. Ed. 2007, 46, 758-760.
44. Inokuma, Y.; Osuka, A. The 10th International KYOTO Conference on New Aspects of Organic Chemistry; The Kinki Chemical Society: Kyoto, Japan, 2006; Poster A-129.
45. (a) Scott, L. T. Angew. Chem., Int. Ed. 2004, 43, 4994-5007.
46. (b) Sakurai, H.; Daiko, T.; Hirao, T. Science 2003, 301, 1878.
47. (c) Sakurai, H.; Daiko, T.; Sakane, H.; Amaya, T.; Hirao, T. J. Am. Chem. Soc. 2005, 127, 11580-11581.
48. Myśliborski, R.; Latos-Grażyński, L.; Szterenberg, L.; Lis, T. Angew. Chem., Int. Ed. 2006, 45, 3670-3674.
49. Pacholska, E.; Latos-Grażyński, L.; Ciunik, Z. Chem. Eur. J. 2002, 8, 5403-5406.
50. (a)Wrackmeyer, B.; Schwarze, B.; Milius, W. Inorg. Chim. Acta. 1996, 241, 87-93.
51. (b) Douglade, G.; Fabre, B. Synth. Met. 2002, 129, 309-314.
52. (a) Köster, R.; Bellut, H.; Hattori, S. Liebigs Ann. Chem. 1968, 720, 1-22.
53. (b) Szarvas, P.; Györi, B.; Emri, J. Acta. Chim. (Budapest) 1971, 70, 1-8.
54. Inokuma, Y.; Kwon, J. H.; Ahn, T. K.; Yoon, M. C.; Kim, D.; Osuka, A. Angew. Chem., Int. Ed. 2006, 45, 961-964.
55. isoindolic-Zn distances are 2.06 and 2.09 Å, respectively. Inokuma, Y.; Ono, N.; Uno, H.; Kim, D. Y.; Nohm S. B.; Kim, D.; Osuka, A. Chem. Commun. 2005, 3782-3784.
56. Cheng, R. J.; Chen, Y. R.; Wang, S. L.; Cheng, C. Y. Polyhedron 1993, 12, 1353-1360.
57. Gold, K. W.; Hodgson, D. J.; Gold, A.; Savrin, J. E.; Toney, G. E. J. Chem. Soc., Chem. Commun. 1985, 563-564.
58. (a) Frisch, M. J.; et al. Gaussian 03. Revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
59. (b) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
60. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
61. Substituent constants were of reported values by McDaniel and Brown. McDaniel, D. H.; Brown, H. C. J. Org. Chem. 1958, 23, 420-427.
62. (a) Bu, J.; Lilienthal, Woods, J. E.; Nohrden, C. E.; Hoang, K. T.; Truong, D.; Smith, D. K.
63. (b) Bento, M. F.; Medeiros, M. J.; Montenegro, M. I.; Beriot, C.; Pletcher, D. J. Electroanal. Chem. 1993, 345, 273-286.
64. Quimby, D. J.; Longo, F. R. J. Am. Chem. Soc. 1975, 97, 5111-5117.
65. (a) Gust, D.; Moore, T. A.; Luttrull, D. K.; Seely, G. R.; Bittersmann, E.; Bensasson, R. V.; Rougee, M.; Land, E. J.; Schryver, F. C. D.; Auweraer, M. V. Photochem. Photobiol. 1990, 51, 419-426.
66. (b) Chirvony, V. S.; Hoek, A.; Schaafsma, T. J.; Pershukevich, P. P.; Filatov, I. V.; Avilov, I. V.; Shishporenok, S. I.; Terekhov, S. N.; Malinovskii, V. L. J. Phys. Chem. B 1998, 102, 9714-9724.
67. (c) Takahashi, K.; Hase, S.; Komura, T.; Imanaga, H.; Ohno, O. Bull. Chem. Soc. Jpn. 1992, 65, 1475-1481.
68. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Kluwer Academic/Plenum Publishers: New York, 1999.
69. Morandeira, A.; Vauthey, E.; Schuwey, A.; Gossauer, A. J. Phys. Chem. A 2004, 108, 5741-5751.
70. Ann, T. K.; Kim, K. S.; Kim, D. Y.; Noh, S. B.; Aratani, N.; Ikeda, C.; Osuka, A.; Kim, D. J. Am. Chem. Soc. 2006, 128, 1700-1704.
71. Li, F.; Yang, S. I.; Ciringh, Y.; Seth, J.; Martin, C. H., III; Singh, D. L.; Kim, D.; Birge, R. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Am. Chem. Soc. 1998, 120, 10001-10017.
72. Based on Hammett's rule, the electron-withdrawing abilities of 4-cyanophenyl and 4-nitrophenyl substituents are similar (only slightly larger in 4-nitrophenyl), but 14d in acetonitrile or methanol showed no fluorescence-quenching behavior at any detection wavelengths (SI). It seems that the intramolecular charge transfer occurs only in 14e.
73. Klein, E.; Lukes, V. J. Phys. Chem. A 2006, 110, 12312-12320.