Fine tuning of photophysical properties of meso-meso-linked ZnII-diporphyrins by dihedral angle control

Chemistry - A European Journal

Volumn 9, Issue 1, 2003, Pages 58-75

  Yoshida, Naoya ^a   Ishizuka, Tomoya ^a   Osuka, Atsuhiro ^a   Jeong, Dae Hong ^b   Cho, Hyun Sun ^b   Kim, Dongho ^b   Matsuzaki, Yoichi ^c   Nogami, Atsushi ^c   Tanaka, Kazuyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Yonsei University   (South Korea)

^c NIPPON STEEL CORPORATION   (Japan)

Author keywords

Copper; Fluorescence spectroscopy; Porphyrinoids; Structure elucidation; Zinc

Indexed keywords

ABSORPTION; CHARGE TRANSFER; FLUORESCENCE; RAMAN SCATTERING; SILVER COMPOUNDS; SULFUR; X RAY CRYSTALLOGRAPHY; ZINC;

ANGLE CONTROL;

PHOTOCHEMICAL REACTIONS;

COPPER; PORPHYRIN DERIVATIVE; ZINC COMPLEX;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; FLUORESCENCE SPECTROSCOPY; PHOTOPHYSICS; PHYSICS; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0037415105     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390004     Document Type: Article

References (64)

1. a) J. P. Collman, F. C. Anson, C. E. Barnes, C. S. Bencosme, T. Geiger, E. R. Evitt, R. P. Kreh, K. Meier, R. B. Pettman, J. Am. Chem. Soc. 1983, 105, 2694;
2. b) C. K. Chang, I. Abdalmuhdi, J. Org. Chem. 1983, 48, 5388.
3. a) F. P. Schwarz, M. Gouterman, Z. Muljiani, D. H. Dolphin, Bioinorg. Chem. 1972, 2, 1;
4. b) J. A. Anton, P. A. Loach, Govindjee, Photochem. Photobiol. 1978, 28, 235;
5. c) I. Tabushi, T. Sasaki, Tetrahedron Lett. 1982, 23, 1913.
6. a) M. R. Wasielewski, Chem. Rev. 1992, 92, 435;
7. b) A. Osuka, N. Mataga, T. Okada, Pure Appl. Chem. 1997, 69, 797;
8. J.-H. Chou, H. S. Nalwa, M. E. Kosal, N. A. Rakow, K. S. Suslick, in The Porphyrin Handbook, Vol. 6 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard) Academic Press, San Diego, 2000, Chapter 41.
9. a) J. L. Sesslar, M. R. Johnson, T.-Y. Ling, S. E. Creager, J. Am. Chem. Soc. 1988, 110, 3659;
10. b) K. Maruyama, A. Osuka, Pure Appl. Chem. 1990, 62, 1511;
11. c) J. M. Zaleski, C. K. Chang, G. E. Leroi, R. I. Cukier, D. G. Nocera, J. Am. Chem. Soc. 1992, 114, 3564;
12. d) T. L. Netzel, M. A. Bergkamp, C. K. Chang, J. Am. Chem. Soc. 1982, 104, 1952.
13. M. R. Wasielewski, in Photoinduced Electron Transfer (Eds.: M. A. Fox, M. Chanon), Elsevier, Amsterdam, 1988, Chapter 1.4.
14. A. Helms, D. Heiler, G. McLendon, J. Am. Chem. Soc. 1991, 113, 4325.
15. A. Osuka, J. Shin, R. Yoneshima, H. Shiratori, T. Ohno, K. Nozaki, Y. Nishimura, I. Yamazaki, S. Taniguchi, T. Shimizu, T. Okada, J. Porphyrins Phthalocyanines 1999, 3, 729.
16. a) A. Osuka, K. Maruyama, J. Am. Chem. Soc. 1988, 110, 4454. The exciton coupling of other covalently linked diporphyrins; see Refs. [2b,c] and b) B. von Maltzan, Z. Naturforsch. Teil A 1985, 40, 389; c) J. L. Sessler, J. Hugdahl, M. R. Johnson, J. Org. Chem. 1986, 51, 2838; d) H. Meier, Y. Kobuke, S. Kugimiya, J. Chem. Soc. Chem. Commun. 1989, 923.
17. a) A. Osuka, K. Maruyama, J. Am. Chem. Soc. 1988, 110, 4454. The exciton coupling of other covalently linked diporphyrins; see Refs. [2b,c] and b) B. von Maltzan, Z. Naturforsch. Teil A 1985, 40, 389; c) J. L. Sessler, J. Hugdahl, M. R. Johnson, J. Org. Chem. 1986, 51, 2838; d) H. Meier, Y. Kobuke, S. Kugimiya, J. Chem. Soc. Chem. Commun. 1989, 923.
18. a) A. Osuka, K. Maruyama, J. Am. Chem. Soc. 1988, 110, 4454. The exciton coupling of other covalently linked diporphyrins; see Refs. [2b,c] and b) B. von Maltzan, Z. Naturforsch. Teil A 1985, 40, 389; c) J. L. Sessler, J. Hugdahl, M. R. Johnson, J. Org. Chem. 1986, 51, 2838; d) H. Meier, Y. Kobuke, S. Kugimiya, J. Chem. Soc. Chem. Commun. 1989, 923.
19. a) A. Osuka, K. Maruyama, J. Am. Chem. Soc. 1988, 110, 4454. The exciton coupling of other covalently linked diporphyrins; see Refs. [2b,c] and b) B. von Maltzan, Z. Naturforsch. Teil A 1985, 40, 389; c) J. L. Sessler, J. Hugdahl, M. R. Johnson, J. Org. Chem. 1986, 51, 2838; d) H. Meier, Y. Kobuke, S. Kugimiya, J. Chem. Soc. Chem. Commun. 1989, 923.
20. a) A. Osuka, K. Maruyama, I. Yamazaki, N. Tamai, Chem. Phys. Lett. 1990, 165, 392;
21. b) A. Osuka, K. Marumaya, N. Mataga, T. Asahi, I. Yamazaki, N. Tamai, J. Am. Chem. Soc. 1990, 112, 4958.
22. a) S. Matile, N. Berova, K. Nakanishi, S. Novkova, I. Philipova, B. Blagoev, J. Am. Chem. Soc. 1995, 117, 7021;
23. b) X. Huang, B. H. Rickman, B. Borhan, N. Berova, K. Nakanishi, J. Am. Chem. Soc. 1998, 120, 6185;
24. c) V. V. Borovkov, J. M. Lintuluoto, M. Fujiki, Y. Inoue, J. Am. Chem. Soc. 2000, 122, 4403.
25. a) A. Osuka, H. Shimidzu, Angew. Chem. 1997, 109, 93; Angew. Chem. Int. Ed. Engl. 1997, 36, 135;
26. a) A. Osuka, H. Shimidzu, Angew. Chem. 1997, 109, 93; Angew. Chem. Int. Ed. Engl. 1997, 36, 135;
27. b) T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono, A. Osuka, Chem. Commun. 1998, 337;
28. c) T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono, A. Osuka, Angew. Chem. 1999, 111, 140; Angew. Chem. Int. Ed. 1999, 38, 176;
29. c) T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono, A. Osuka, Angew. Chem. 1999, 111, 140; Angew. Chem. Int. Ed. 1999, 38, 176;
30. d) N. Aratani, A. Osuka, Y. H. Kim, D. H. Jeong, D. Kim, Angew. Chem. 2000, 112, 1517; Angew. Chem. Int. Ed. 2000, 39, 1458;
31. d) N. Aratani, A. Osuka, Y. H. Kim, D. H. Jeong, D. Kim, Angew. Chem. 2000, 112, 1517; Angew. Chem. Int. Ed. 2000, 39, 1458;
32. e) H. S. Cho, N. W. Song, Y. H. Kim, S. C. Jeoung, S. Hahn, D. Kim, S. K. Kim, N. Yoshida, A. Osuka, J. Phys. Chem. B 2000, 104, 3287;
33. f) A. A. Bhuiyan, J. Seth, N. Yoshida, A. Osuka, D. F. Bocian, J. Phys. Chem. A 2000, 104, 10757;
34. g) Y. H. Kim, D. H. Jeong, D. Kim, S. C. Jeoung, H. S. Cho, S. K. Kim, N. Aratani, A. Osuka, J. Am. Chem. Soc. 2001, 123, 76.
35. Several groups reported independently the synthesis of meso-meso-coupled diporphyrins: a) K. Susumu, T. Shimidzu, K. Tanaka, H. Segawa, Tetrahedron Lett. 1996, 37, 8399; b) R. G. Khoury, L. Jaquinod, K. M. Smith, Chem. Commun. 1997, 1057; c) M. O. Senge, X. Feng, Tetrahedron Lett. 1999, 40, 4165; d) X. Shi, L. S. Liebeskind, J. Org. Chem. 2000, 65, 1665.
36. Several groups reported independently the synthesis of meso-meso-coupled diporphyrins: a) K. Susumu, T. Shimidzu, K. Tanaka, H. Segawa, Tetrahedron Lett. 1996, 37, 8399; b) R. G. Khoury, L. Jaquinod, K. M. Smith, Chem. Commun. 1997, 1057; c) M. O. Senge, X. Feng, Tetrahedron Lett. 1999, 40, 4165; d) X. Shi, L. S. Liebeskind, J. Org. Chem. 2000, 65, 1665.
37. Several groups reported independently the synthesis of meso-meso-coupled diporphyrins: a) K. Susumu, T. Shimidzu, K. Tanaka, H. Segawa, Tetrahedron Lett. 1996, 37, 8399; b) R. G. Khoury, L. Jaquinod, K. M. Smith, Chem. Commun. 1997, 1057; c) M. O. Senge, X. Feng, Tetrahedron Lett. 1999, 40, 4165; d) X. Shi, L. S. Liebeskind, J. Org. Chem. 2000, 65, 1665.
38. Several groups reported independently the synthesis of meso-meso-coupled diporphyrins: a) K. Susumu, T. Shimidzu, K. Tanaka, H. Segawa, Tetrahedron Lett. 1996, 37, 8399; b) R. G. Khoury, L. Jaquinod, K. M. Smith, Chem. Commun. 1997, 1057; c) M. O. Senge, X. Feng, Tetrahedron Lett. 1999, 40, 4165; d) X. Shi, L. S. Liebeskind, J. Org. Chem. 2000, 65, 1665.
39. a) M. Goutermann, J. Mol. Spectrosc. 1961, 6, 138;
40. b) M. Kasha, H. R. Rawls, M. A. El-Bayoumi, Pure Appl. Chem. 1965, 11, 371.
41. H. S. Cho, D. H. Jeong, M. C. Yoon, Y. H. Kim, Y. R. Kim, D. Kim, S. C. Jeoung, S. K. Kim, N. Aratani, H. Shinmori, A. Osuka, J. Phys. Chem. A 2001, 105, 4200.
42. A preliminary short report of the present work has been published: N. Yoshida, A. Osuka, Org. Lett. 2000, 2, 2963.
43. N. Yoshida, A. Osuka, Tetrahedron Lett. 2000, 41, 9287.
44. II diporphyrins which have dihedral angles of nearly 90°: N. Aratani, A. Osuka, unpublished results.
45. N. Yoshida, N. Aratani, A. Osuka, Chem. Commun. 2000, 197.
46. P. G. Seybold, M. Goutermann, J. Mol. Spectrosc. 1969, 31, 1.
47. a) X.-Y. Li, R. S. Czernuszewicz, J. R. Kincaid, Y. O. Su, T. G. Spiro, J. Phys. Chem. 1990, 94, 31;
48. b) D. H. Jeong, M.-C. Yoon, S. M. Jang, D. Kim, D. W. Cho, N. Yoshida, N. Aratani, A. Osuka, J. Phys. Chem. A 2002, 106, 2359.
49. N. Ohta, Y. Iwaki, T. Ito, I. Yamazaki, A. Osuka, J. Phys. Chem. B 1999, 103, 11242.
50. a) T. P. Wijesekera, J. B. Paine III, D. Dolphin, F. W. B. Einstein, T. Jones, J. Am. Chem. Soc. 1983, 105, 6747;
51. b) M. Momenteau, J. Mispelter, B. Loock, E. Bisagni, J. Chem. Soc. Perkin Trans. 1 1983, 189;
52. c) U. Simonis, F. A. Walker, P. L. Lee, B. J. Hanquet, D. J. Meyerhoff, W. R. Scheidt, J. Am. Chem. Soc. 1987, 109, 2659.
53. S. F. Mason, R. H. Seal, D. R. Roberts, Tetrahedron 1974, 30, 1671.
54. O. Bilsel, J. Rodriguez, S. N. Milam, P. A. Gorlin, G. S. Girolami, K. S. Suslick, D. Holten, J. Am. Chem. Soc. 1992, 114, 6528.
55. J. D. Petke, G. M. Maggiora, J. Chem. Phys. 1986, 84, 1640.
56. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, 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, 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. AlLaham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, 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.7, Gaussian, Pittsburgh, PA, 1998.
57. J. Almlöf, T. H. Fischer, P. G. Gassman, A. Ghosh, M. Häser, J. Phys. Chem. 1993, 97, 10964.
58. R. Ditchfield, W. J. Hehre, J. A. Pople, J. Chem. Phys. 1971, 54, 724.
59. S. Huzinaga, J. Andzelm, M. Klobukowski, E. Radzio-Andzelm, Y. Sakai, H. Tatewaki, Gaussian Basis Sets for Molecular Calculations, Elsevier, New York, 1984.
60. J. E. Ridley, M. C. Zerner, Theor. Chim. Acta 1973, 32, 111.
61. K. Nishimoto, N. Mataga, Z. Phys. Chem. 1957, 12, 335.
62. B. J. Orr, J. F. Ward, Mol. Phys. 1971, 20, 513.
63. S. Mukamel, S. Tretiak, T. Wagersreiter, V. Chernyak, Science 1997, 277, 781.
64. M. Gouterman, J. Chem. Phys. 1959, 30, 1139.