Regioisomerically controlled self-aggregation of zinc 3-hydroxymethyl-13- formyl-chlorin/porphyrin and their 3,13-inverted pigments

Journal of Organic Chemistry

Volumn 72, Issue 7, 2007, Pages 2443-2451

  Kunieda, Michio ^a   Tamiaki, Hitoshi ^a  

^a RITSUMEIKAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIOCHLOROPHYLLS; PHOTOSYNTHETIC BACTERIA; REGIOISOMERS; SOLID FILMS;

ABSORPTION SPECTRA; BACTERIA; CHLOROPHYLL; DEHYDROGENATION; ISOMERS; MOLECULAR MODELING; PIGMENTS; PORPHYRINS;

ZINC COMPOUNDS;

PIGMENT; PORPHYRIN; TRITON X 100; UNCLASSIFIED DRUG; ZINC 3 HYDROXYMETHYL 13 FORMYLCHLORIN;

ARTICLE; INFRARED SPECTROSCOPY; LIGHT HARVESTING SYSTEM; MOLECULAR INTERACTION; OLIGOMERIZATION; REACTION ANALYSIS; SYNTHESIS;

METALLOPORPHYRINS; MICELLES; MOLECULAR STRUCTURE; OCTOXYNOL; PORPHYRINS; SOLUTIONS; SPECTRUM ANALYSIS; STEREOISOMERISM;

EID: 34047238691     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0623282     Document Type: Article

References (46)

1. (a) Blankenship, R. E.; Matsuura, K. In Light Harvesting Antennas in Photosynthesis; Green, B. R., Parson, W. W., Eds.; Kluwer Academic Publisher: Dordrecht, The Netherlands, 2003; pp 195-217.
2. (b) Tamiaki, H. Photochem. Photobiol. Sci. 2005, 4, 675-680.
3. (c) Miyatake. T.; Tamiaki, H. J. Photochem. Photobiol., C 2005, 6, 89-107.
4. (a) Smith, K. M.; Kehres, L. A.; Fajer, J. J. Am. Chem. Soc. 1983, 105, 1387-1389.
5. (b) Brune, D. C.; Nozawa, T.; Blankenship, R. E. Biochemistry 1987, 26, 8644-8652.
6. (c) Holzwarth, A. R.; Griebenow, K.; Schaffner, K. J. Photochem. Photobiol., A 1992, 65, 61-71.
7. (d) Uehara, K.; Oison, J. M. Photosynth. Res. 1992, 33, 251-257.
8. (e) Hirota, M.; Moriyama, T.; Shimada, K.; Miller, M.; Olson, J. M.; Matsuura, K. Biochim. Biophys. Acta 1992, 1099, 271-274.
9. (f) Tamiaki, H. Coord. Chem. Rev. 1996, 148, 183-197.
10. (g) Saga, Y.; Matsuura, K.; Tamiaki, H. Photochem. Photobiol. 2001, 74, 72-80.
11. (h) Mizoguchi, T.; Saga, Y.; Tamiaki, H. Photochem. Photobiol. Sci 2002, 1, 780-787.
12. (i) Saga. Y.; Akai, S.; Miyatake, T.; Tamiaki, H. Bioconjugate Chem. 2006, 17, 988-994.
13. (a) Tamiaki, H.; Amakawa, M.; Shimono, Y.: Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92-99.
14. (b) Yagai, S.; Miyatake, T.; Shimono, Y.; Tamiaki, H. Photochem. Photobiol. 2001, 73, 153-163.
15. (c) Yagai, S.; Tamiaki, H. J. Chem. Soc., Perkin Trans. 1 2001, 3135-3144.
16. (d) Tamiaki, H.; Amakawa, M.; Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 2002, 71, 59-67.
17. (e) Tamiaki, H.; Omoda, M.; Saga, Y.; Morishita, H. Tetrahedron 2003, 59, 4337-4350.
18. (f) Tamiaki, H.; Kimura, S.; Kimura, T. Tetrahedron 2003, 59, 7423-7435.
19. (g) Balaban, T. S.; Bhise, A. D.; Fischer, M.; Linke-Schaetzel, M.; Roussel, C.; Vanthuyne, N. Angew. Chem., Int. Ed. 2003, 42, 2140-2144.
20. (h) Sasaki, S.; Tamiaki, H. Bull. Chem. Soc. Jpn. 2004, 77, 797-800.
21. (i) Balaban, T. S.; Tamiaki, H.; Holzwarth, A. R. In Supramolecular Dye Chemistry; WUrthner, F., Ed.; Topics in Current Chemistry, Vol. 258; Springer: Heidelberg. Germany, 2005; pp 1-38.
22. (j) Tamiaki, H.; Kitamoto, H.; Watanabe, T.; Shibata, R. Photochem. Photobiol. 2005. 81, 170-176.
23. (k) Balaban, T. S. Acc. Chem. Res. 2005, 38, 612-623.
24. (l) Mizoguchi, T.; Shoji, A.; Kunieda, M.; Miyashita, H.; Tsuchiya, T.; Mimuro, M.; Tamiaki, H. Photochem. Photobiol. Sci. 2006, 5, 291-299.
25. Balaban, T. S.; Linke-Schaetzel, M.; Bhise, A. D.; Vanthuyne. N.; Roussel, C. Eur. J. Org. Chem. 2004, 3919-3930.
26. (a) Sasaki, S.; Omoda, M.; Tamiaki, H. J. Photochem. Photobiol., A 2004, 162, 307-315.
27. (b) Huber, V.; Katterle, M.; Lysetska, M.; Würthner, F. Angew. Chem., Int. Ed. 2005, 44, 3147-3151.
28. (a) Kunieda, M.; Mizoguchi, T.; Tamiaki, H. Photochem. Photobiol. 2004, 79, 55-61.
29. (b) Kunieda, M.; Tamiaki. H. J. Org. Chem. 2005, 70, 820-828.
30. (a) Jesorka, A.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. Angew. Chem., Int. Ed. 1996, 35, 2861-2863.
31. (b) Yagai, S.; Miyatake, T.; Tamiaki, H. J. Photochem. Photobiol., B 1999, 52, 74-85.
32. (c) Yagai, S.; Miyatake, T.; Tamiaki, H. J. Org. Chem. 2002, 67, 49-58.
33. Scheer, H. In Light Harvesting Antennas in Photosynthesis; Green, B. R., Parson, W. W., Eds.; Kluwer Academic Publisher: Dordrecht, The Netherlands, 2003; pp 29-81.
34. Tamiaki, H.; Shibata, R.; Mizoguchi, T. Photochem. Photobiol. 2007, 83, 152-162.
35. (a) Tamiaki, H.; Shimamura, Y.; Yoshimura, H.; Pandey, S. K.; Pandey, R. K. Chem. Lett. 2005, 34, 1344-1345.
36. (b) Kunieda, M.; Tamiaki, H. Eur. J. Org. Chem. 2006, 2352-2361.
37. Smith, K. M.; Lewis, W. M. Tetrahedron, Suppl. 1981, 399-403.
38. Tamiaki, H.; Watanabe, T.; Miyatake, T. J. Porphyrins Phthalocyanines 1999, 3, 45-52.
39. (a) Tamiaki, H.; Kouraba, M. Tetrahedron 1997, 53, 10677-10688.
40. (b) Laha, J. K.; Muthiah, C.; Taniguchi, M.; McDowell, B. E.; Ptaszek, M.; Lindsey, J. S. J. Org. Chem. 2006, 71, 4092-4102.
41. Oba, T.; Tamiaki, H. Bioorg. Med. Chem. 2005, 13, 5733-5739.
42. (a) Abraham, R. J.; Rowan, A. E.; Smith, N. W.; Smith, K. M. J. Chem. Soc., Perkin Trans. 2 1993, 1047-1059.
43. (b) Sato, H.; Uehara, K.; Ishii, T.; Ozaki, Y. Biochemistry 1995, 34, 7854-7860.
44. 2-C=O group unconjugated to macrocyclic π-system gave no signal in the RR spectroscopy (see Figure S2 in Supporting Information). The RR spectrum of 2 having less absorbance at the Ar-laser excited wavelength (457.9 nm) was covered by background.
45. Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 1994, 41, 225-233.
46. Wang, Z.-Y.; Umetsu, M.; Kobayashi, M.; Nozawa, T. J. Am. Chem. Soc. 1999, 121, 9363-9369.