Synthesis, spectroscopic, and electrochemical studies of 1,2-naphthalene-ring-fused tetraazachlorins, -bacteriochlorins, and -isobacteriochlorins: The separation and characterization of structural isomers

Chemistry - A European Journal

Volumn 11, Issue 4, 2005, Pages 1235-1250

  Makarova, Elena A ^a   Fukuda, Takamitsu ^b   Luk'yanets, Evgeny A ^a   Kobayashi, Nagao ^b  

^a Organic Intermediates and Dyes Institute   (Russian Federation)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

Density functional calculations; IR spectroscopy; Phthalocyanines; Porphyrinoids; UV Vis spectroscopy

Indexed keywords

CARBOXYLIC ACIDS; ELECTROCHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); THIN LAYER CHROMATOGRAPHY;

ELECTRONIC ABSORPTION; MAGNETIC CIRCULAR DICHROISM (MCD) SPECTROSCOPY; TETRAAZABACTERIOCHLORINS (TABC); TETRAAZAISOBACTERIOCHLORINS (TAIBC);

NAPHTHALENE;

1,2 NAPHTHALENE DERIVATIVE; 2,3 NAPHTHALENE DERIVATIVE; BACTERIOCHLORIN; CHLORINE DERIVATIVE; ISOBACTERIOCHLORIN DERIVATIVE; NAPHTHALENE; NAPHTHALENE DERIVATIVE; TETRAAZACHLORIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; ELECTROCHEMICAL ANALYSIS; GEOMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; MAGNETISM; MATHEMATICAL ANALYSIS; MOLECULAR INTERACTION; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; SEPARATION TECHNIQUE; SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; ZINDO METHOD;

AZA COMPOUNDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; CIRCULAR DICHROISM; ELECTROCHEMISTRY; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHALENES; PORPHYRINS; QUANTUM THEORY; REFERENCE STANDARDS; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 14544271865     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400845     Document Type: Article

References (47)

1. a) Phthalocyanines-Properties and Applications, Vols. I-IV (Eds.: C. C. Leznoff, A. B. P. Lever), VCH, New York, 1989, 1993, 1993, 1996;
2. b) Phthalocyanines-Chemistry and Functions (Eds.: H. Shirai, N. Kobayashi), IPC, Tokyo, 1997 (in Japanese).
3. a) Porphyrins and Metalloporphyrins (Ed.: K. M. Smith), Elsevier, Amsterdam, 1975;
4. b) The Porphyrins, Vols. 1-7 (Ed.: D. Dolphin), Academic Press, New York, 1978;
5. c) The Porphyrin Handbook, Vols. 1-20 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 1999, 2003.
6. a) H. Miwa, E. A. Makarova, K. Ishii, E. A. Luk'yanets, N. Kobayashi, Chem. Eur. J. 2002, 8, 1082;
7. b) E. A. Makarova, G. V. Korolyova, E. A. Luk'yanets, Zh. Obshch. Khim. 2001, 71, 874;
8. c) E. A. Makarova, G. V. Korolyova, E. A. Luk'yanets, Russian Patent, 2188200, 2000.
9. a) E. A. Makarova, G. V. Korolyova, E. A. Luk'yanets, Abstr. 1st Int. Conf. on Porphyrins and Phthalocyanines 2000, Dijon, France, P482;
10. b) T. Fukuda, E. A. Makarova, E. A. Luk'yanets, N. Kobayashi, Abstr. 2nd Int. Conf. on Porphyrins and Phthalocyanines 2002, Kyoto, Japan, P292.
11. T. Fukuda, E. A. Makarova, E. A. Luk'yanets, N. Kobayashi, Chem. Eur. J. 2004, 10, 117.
12. E. A. Makarova, N. Kobayashi, E. A. Luk'yanets, Abtsr. 2nd Int. Conf. on Porphyrins and Phthalocyanines 2002, Kyoto, Japan, P496.
13. E. F. Bradbook, R. P. Linstead, J. Chem. Soc. 1936, 1744.
14. M. Hanack, G. Renz, J. Strähle, S. Schmid, Chem. Ber. 1988, 121, 1479.
15. M. Hanack, G. Renz, J. Strähle, S. Schmid, J. Org. Chem. 1991, 56, 3501.
16. V. M. Negrimovskii, M. Bouvet, E. A. Luk'yanets, J. Simon, J. Porphyrins Phthalocyanines 2000, 4, 248.
17. E. H. Gacho, Ph.D. Thesis, Hokkaido University, 2001.
18. E. H. Gacho, T. Naito, T. Inabe, T. Fukuda, N. Kobayashi, Chem. Lett. 2001, 260.
19. M. S. Newman, B. Dhawan, M. M. Hashem, V. K. Khanna, J. M. Springer, J. Org. Chem. 1976, 41, 3925.
20. F. Bergmann, J. Szmuszkowicz, G. Fawaz, J. Am. Chem. Soc. 1947, 69, 1773.
21. To correct the dispersion of the molar absorption coefficient (ε) at 720 nm for each isomer, evaluated areas in Figure 4 divided by ε were employed as the formation ratio.
22. G. Schmid, M. Sommerauer, M. Geyer, M. Hanack in Phthalocyanines- Properties and Applications, Vol. 4 (Eds.: C. C. Leznoff, A. B. P. Lever), VCH, New York, 1996, Chapter 1.
23. N. Kobayashi, H. Konami in Phthalocyanine-Properties and Applications, Vol. 4 (Eds.: C. C. Leznoff, A. B. P. Lever), VCH, New York, 1996, Chapter 9.
24. For examples of metalloPcs showing split Q bands, see: a) N. Kobayashi, T. Ashida, T. Osa, Chem. Lett. 1992, 1567;
25. b) N. Kobayashi, T. Fukuda, J. Am. Chem. Soc. 2002, 124, 8021;
26. c) N. Kobayashi, H. Miwa, V. N. Nemykin, J. Am. Chem. Soc. 2002, 124, 8007;
27. d) R. W. Begland, D. R. Hartter, F. N. Jones, D. J. Sam, W. A. Sheppard, O. W. Webster, F. J. Weigert, J. Org. Chem. 1974, 39, 2341;
28. e) A. G. Montalban, W. Jarrel, E. Riguet, Q. J. McCubbin, M. E. Anderson, A. J. P. White, A. G. M. Barrett, B. M. Hoffman, J. Org. Chem. 2000, 65, 2472;
29. f) T. P. Forsyth, D. B. G. Williams, A. G. Montalban, C. L. Stern, A. G. M. Barrett, B. M. Hoffman, J. Org. Chem. 1998, 63, 331;
30. g) J. W. Sibert, T. F. Baumann, D. J. Williams, A. J. P. White, A. G. M. Barrett, B. M. Hoffman, J. Am. Chem. Soc. 1996, 118, 10487;
31. h) J. A. Elvidge, J. H. Golden, R. P. Linstead, J. Chem. Soc. 1957, 2466;
32. i) Y. Ikeda, H. Konami, M. Hatano, K. Mochizuki, Chem. Lett. 1992, 763;
33. j) M. Aoudia, G. Cheng, V. O. Kennedy, M. E. Kenney, M. A. J. Rodgers, J. Am. Chem. Soc. 1997, 119, 6029;
34. k) P. Margaron, R. Langlois, J. E. van Lier, S. Gaspard, J. Photochem. Photobiol. B 1992, 14, 187;
35. l) S. V. Kudrevich, H. Ali, J. E. van Lier, J. Chem. Soc., Perkin Trans. 1 1994, 2767;
36. m) U. Michelsen, H. Kliesch, G. Schnurpfeil, A. K. Sobbi, D. Wöhrle, Photochem. Photobiol. 1996, 64, 694;
37. n) A. Weitemeyer, H. Kliesch, D. Wöhrle, J. Org. Chem. 1995, 60, 4900.
38. A. Tajiri, J. Z. Winkler, Naturforsch. A 1983, 38, 1263.
39. A. Kaito, T. Nozawa, T. Yamamoto, M. Hatano, Y. Orii, Chem. Phys. Lett. 1977, 52, 154.
40. N. Kobayashi, T. Fukuda, D. Lelièvre, Inorg. Chem. 2000, 39, 3632.
41. N. Kobayashi, T. Ishizaki, K. Ishii, H. Konami, J. Am. Chem. Soc. 1999, 121, 9096.
42. N. Kobayashi, Y. Higashi, T. Osa, Chem. Lett. 1994, 1813.
43. N. Kobayashi, R. Kondo, S. Nakajima, T. Osa, J. Am. Chem. Soc. 1990, 112, 9640.
44. For example, see: M. Gouterman, H. Wagnière, L. C. Snyder, J. Mol. Spectrosc. 1963, 11, 108.
45. Gaussian 98, Revision A.11.3, 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, Inc., Pittsburgh, PA, 2002.
46. W. Barbe, H.-D. Beckhaus, H.-J. Lindner, C. Rüchardt, Chem. Ber. 1983, 116, 1017.
47. E. F. Bradbook, R. P. Linstead, J. Chem. Soc. 1936, 1739.