Absorption, magnetic circular dichroism, IR spectra, electrochemistry, and molecular orbital calculations of monoaza- and opposite diazaporphyrins

European Journal of Inorganic Chemistry

Volumn , Issue 8, 2004, Pages 1621-1629

  Ogata, Hiroshi ^a   Fukuda, Takamitsu ^a   Nakai, Katsunori ^a   Fujimura, Yuiehi ^a   Neya, Saburo ^b   Stuzhin, Pavel A ^c   Kobayashi, Nagao ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

^c IVANOVO STATE UNIVERSITY OF CHEMISTRY AND TECHNOLOGY   (Russian Federation)

Author keywords

Cyclic voltammetry; Density functional calculations; Magnetic circular dichroism; Porphyrinoids; UV; Vis spectroscopy

Indexed keywords

CIRCULAR DICHROISM SPECTROSCOPY; COPPER COMPOUNDS; CYCLIC VOLTAMMETRY; DICHROISM; MOLECULAR ORBITALS; ULTRAVIOLET VISIBLE SPECTROSCOPY;

DENSITY-FUNCTIONAL CALCULATIONS; IR SPECTRUM; MAGNETIC CIRCULAR DICHROISMS; METAL FREE; MOLECULAR ORBITAL CALCULATIONS; PORPHYRINOIDS; Q-BANDS; SPLITTINGS; UV; VIS SPECTROSCOPY;

DENSITY FUNCTIONAL THEORY;

HETEROCYCLIC COMPOUND; NITROGEN; PORPHYRIN DERIVATIVE;

ABSORPTION; ARTICLE; CALCULATION; CIRCULAR DICHROISM; CYCLIC POTENTIOMETRY; DENSITY FUNCTIONAL THEORY; DIFFERENTIAL PULSE VOLTAMMETRY; ELECTROCHEMISTRY; INFRARED SPECTROSCOPY; MOLECULAR DYNAMICS;

EID: 4544247515     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200300825     Document Type: Article

References (64)

1. H. Fischer, W. Friedrich, Justus Liebigs Ann. Chem. 1936, 523, 154-164.
2. F. Endermann, H. Fischer, Justus Liebigs Ann. Chem. 1939, 538, 172-194.
3. H. Fischer, H. Orth, Die Chemie des Pyrroles, Akad. Verlag, Leipzig, 1940, Vol. II-ii, pp. 408-11.
4. H. Fischer, H. Harberland, A. Muller, Justus Liebigs Ann. Chem. 1935, 521, 122-128.
5. R. L. N. Harris, A. W. Johnson, I. T. Kay, J. Chem. Soc., C 1966, 22-29.
6. J. Engel, A. Gossauer, A. W. Johnson, J. Chem. Soc., Perkin Trans. 1 1978, 871-875.
7. A. M. Abeysekera, R. Grigg, J. F. Malone, J. T. King, J. O. Morley, J. Chem. Soc., Perkin Trans. 2 1985, 395-402.
8. R. K. Pandey, H. Zhou, K. Gerzevske, K. M. Smith, J. Chem. Soc., Chem. Commun. 1992, 183-185.
9. J. P. Singh, L. Y. Xie, D. Dolphin, Tetrahedron Lett. 1995, 36, 1567-1570.
10. W. Metzger, H. Fischer, Justus Liebigs Ann. Chem. 1937, 527, 1-37.
11. H. Fischer, A. Muller, Justus Liebigs Ann. Chem. 1937, 528, 1-8.
12. O. G. Khelevina, N. V. Chizhova, P. A. Stuzhin, A. S. Semeikin, B. D. Berezin, Russ. J. Coord. Chem. (Engl. Transl) 1996, 22, 811-814.
13. O. G. Khelevina, N. V. Chizhova, P. A. Stuzhin, A. S. Semeikin, B. D. Berezin, Russ. J. Phys. Chem. (Engl. Transl) 1997, 71, 74-78.
14. S. Saito, H. A. Itano, J. Chem. Soc., Perkin Trans. 1 1986, 1-7.
15. A. L. Balch, M. M. Olmstead, N. Safari, Inorg. Chem. 1993, 32, 291-296.
16. J. H. Fuhrhop, P. Kruger, W. S. Sheldrick, Justus Liebigs Ann. Chem. 1977, 339-359.
17. R. Grigg, R. J. Hamilton, M. L. Jozefowicz, C. H. Rochester, R. J. Terrell, H. Wickwar, J. Chem. Soc., Perkin Trans. 2 1973, 407-413.
18. J. A. Clarke, P. J. Dawson, R. Grigg, C. H. Rochester, J. Chem. Soc, Perkin Trans. 2 1973, 414-416.
19. S. S. Dvornikov, V. N. Knyukshto, V. A. Kuzmitsky, A. M. Shluga, K. N. Solovyov, J. Lumin. 1981, 23, 373-392.
20. G. P. Gurinovich, G. N. Sinyakov, A. M. Shulga, Izv. Akad. Nauk. SSSR. Ser. Fiz. 1970, 34, 620-624.
21. V. A. Mashenkov, K. N. Solov'ev, A. E. Turkova, N. A. Yushkevich, Zh. Prikl. Specktrosk. 1974, 21, 73-81.
22. F. P. Monforts, B. Gerlach, Tetrahedron Lett. 1992, 33, 1985-1988.
23. S. Neya, T. Kaku, N. Funasaki, Y. Shiro, T. Iizuka, K. Imai, H. Hori, J. Biol. Chem. 1995, 270, 13118-13123.
24. M. J. Stillman, T. Nyokong, in Phthalocyanines - Properties and Applications (Ed.: C. C. Leznoff, A. B. P. Lever), VCH, New York, 1989, Vol.1, Chapter 3, pp 133-289.
25. [25a] N. Kobayashi, F. Furuya, G.-C. Yug, H. Wakita, M. Yokomizo, N. Ishikawa, Chem. Eur. J. 2002, 8, 1474-1484.
26. [25b] N. Kobayashi, Bull. Chem. Soc. Jpn. 2002, 75, 1-19.
27. [25c] Y.-H. TSE, N. Kobayashi, A. B. P. Lever, Collect. Czech. Chem. Commun. 2001, 66, 338-354.
28. [25d] N. Kobayashi, A. Muranaka, Chem. Commun. 2000, 1855-1856.
29. [25e] N. Kobayashi, A. Muranaka, K. Ishii, Inorg. Chem. 2000, 39, 2256-2257.
30. [25f] N. Kobayashi, T. Fukuda, D. Lelievre, Inorg. Chem. 2000, 39, 3632-3637.
31. [25g] N. Kobayashi, R. Higashi, B. C. Titeca, F. Lamote, A. Ceulemans, J. Am. Chem. Soc. 1999, 121, 12018-12028.
32. [25h] N. Kobayashi, Chem. Commun. 1998, 487-488.
33. [25i] N. Kobayashi, H. Lam, W. A. Nevin, P. Janda, C. C. Leznoff, T. Koyama, A. Monden, H. Shirai, J. Am. Chem. Soc. 1994, 116, 879-890.
34. [25j] N. Kobayashi, Y. Kobayashi, T. Osa, J. Am. Chem. Soc. 1993, 115, 10994-10995.
35. [26a] N. Kobayashi, J. Mack, K. Ishii, M. J. Stillman, Inorg. Chem. 2002, 41. 5350-5363.
36. [26b] N. Kobayashi, T. Fukuda, J. Am. Chem. Soc. 2002, 124, 8021-8034.
37. [26c] N. Kobayashi, H. Miwa, V. N. Nemykin, J. Am. Chem. Soc. 2002, 124, 8007-8020.
38. [26d] T. Fukuda, J. R. Stork, R. J. Potucek, M. M. Olmstead, B. C. Noll, N. Kobayashi, W. S. Durfee, Angew. Chem. Int. Ed. 2002, 41, 2565-2568.
39. [26e] H. Miwa, E. A. Makarova, K. Ishii, E. A. Luk'yanets, N. Kobayashi, Chem. Eur J. 2002, 8, 1082-1090.
40. [26f] N. Kobayashi, S. Inagaki, V. N. Nemykin, T. Nonomura, Angew. Chem. Int. Ed. 2001, 40, 2710-2712.
41. [26g] N. Kobayashi, T. Nonomura, K. Nakai, Angew Chem. Int. Ed. 2001, 40, 1300-1303.
42. [26h] N. Kobayashi, A. Muranaka, V. N. Nemykin, Tetrahedron Lett. 2001, 42, 913-915.
43. [26i] V. N. Nemykin, N. Kobayashi, Chem. Commun. 2001, 165-166.
44. [26j] T. Nyokong, F. Furuya, N. Kobayashi, D. Du, W. Liu, J. Jiang, Inorg. Chem. 2000, 39, 128-135.
45. [26k] J. Mack, N. Kobayashi, C. C. Lezonoff, M. J. Stillman, Inorg. Chem. 1997, 36, 5624-5634.
46. [26l] N. Kobayashi, M. Togashi, T. Osa, K. Ishii, S. Yamauchi, H. Hino, J. Am. Chem. Soc. 1996, 118, 1073-1085.
47. Y. Mie, K. Sonoda, S. Neya, N. Funasaki, I. Taniguchi, Bioelectrochem. Bionerg. 1998, 46, 175-184.
48. K. M. Smith, Porphyrins and Metalloporphyrins, Elsevier, Holland, 1976.
49. 00 band at 339 and 586 nm, respectively, in the same solvent, and this value becomes about 0.6.[37]
50. [30a] A. Kaito, T. Nozawa, T. Yamamoto, M. Hatano, Y. Orii, Chem. Phys. Lett. 1977, 52, 154-160.
51. [30b] A. Tajiri, J. Z. Winkler, Naturforsch. 1983, 38a, 1263-1269.
52. [31a] J. Michl, J. Am. Chem. Soc. 1978, 100, 6801-6811.
53. [31b] J. Michl, J. Am. Chem. Soc 1978, 100, 6812-6818.
54. [31c] J. D. Keegan, A. M. Stolzenberg, Y. Lu, R. E. Linder, G. Barth, A. Moscowitz, E. Bunnenberg, C. Djerassi, J. Am. Chem. Soc. 1982, 104, 4305-4317.
55. J. H. Fuhrhop, K. M. Kadish, D. G. Davis, J. Am. Chem. Soc. 1973, 95, 5140-5147.
56. A conceptual explanation on how the LUMO energy changes depending on the number and position of the meso-nitrogen atoms has already been reported: K. N. Solovyov, V. A. Mashenkov, T. F. Kachura, Opt. Spect. 1969, 27, 24-29.
57. [34a] A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
58. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
59. T. Fukuda, E. M. Makarova, E. A. Luk'yanets, N. Kobayashi, Chem. Eur. J. 2004, 10, 117-133.
60. E. M. Makarova, T. Fukuda, E. A. Luk'yanets, N. Kobayashi, submitted.
61. N. Kobayashi, H. Miwa, H. Isago, T. Tomura, Inorg. Chem. 1999, 38. 479-485.
62. R. K. Pandey, K. R. Gerzevske, H. Zhou, K. M. Smith, J. Chem. Soc., Perkin. Trans. 1 1994, 971-977.
63. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery. Jr, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, D. D. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.11.3, Gaussian, Inc., Pittsburgh, PA, 2002.
64. M. W. Wong, Chem. Phys. Lett. 1996, 256, 391-399.