Synthesis, spectroscopy, and semiempirical study of a novel porphyrin- flavin dyad

Chemistry - A European Journal

Volumn 5, Issue 11, 1999, Pages 3208-3220

  Hermann, Dominik T ^b   Schindler, Anne Christina ^b   Polborn, Kurt ^b   Gompper, Rudolf ^b   Stark, Susanne ^a,c   Parusel, Andreas B J ^a,c,d   Grabner, Gottfried ^a   Köhler, Gottfried ^a,c  

^a UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSITY OF MUNICH   (Germany)

^c Institute for Space Dosimetry   (Austria)

^d NASA AMES RESEARCH CENTER   (United States)

Author keywords

Electron transfer; Flavins; Fluorescence spectroscopy; Photosynthesis; Porphyrinoids

Indexed keywords

AROMATIC COMPOUND; PORPHYRIN;

ARTICLE; CHEMICAL ANALYSIS; ELECTRON TRANSPORT; ENERGY TRANSFER; PHOTOSYNTHESIS; POTENTIOMETRY; SPECTROSCOPY; SYNTHESIS;

EID: 0032704970     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19991105)5:11<3208::AID-CHEM3208>3.0.CO;2-O     Document Type: Article

References (92)

1. a) V. Balzani, F. Scandola, Supramolecular Photochemistry; Ellis Horwood, Chichester, 1991, p. 161-196, 355-394;
2. b) D. Gust, Nature 1997, 386, 21;
3. c) S. Speiser, Chem. Rev. 1996, 96, 1953.
4. a) J. Deisenhofer, H. Michel, Angew. Chem. 1989, 101, 872; Angew. Chem. Int. Ed. Engl. 1989, 28, 829;
5. a) J. Deisenhofer, H. Michel, Angew. Chem. 1989, 101, 872; Angew. Chem. Int. Ed. Engl. 1989, 28, 829;
6. b) R. Huber, Angew. Chem. 1989, 101, 849; Angew. Chem. Int. Ed. Engl. 1989, 28, 848.
7. b) R. Huber, Angew. Chem. 1989, 101, 849; Angew. Chem. Int. Ed. Engl. 1989, 28, 848.
8. a) M. R. Wasielewski, Chem. Rev. 1992, 34, 435;
9. b) H. Kurreck, M. Huber, Angew. Chem. 1995, 107, 929; Angew. Chem. Int. Ed. Engl. 1995, 34, 849;
10. b) H. Kurreck, M. Huber, Angew. Chem. 1995, 107, 929; Angew. Chem. Int. Ed. Engl. 1995, 34, 849;
11. c) D. Gust, T. A. Moore, Top. Curr. Chem. 1991, 159, 103-151;
12. d) D. Gust, T. A. Moore, A. L. Moore, Acc. Chem. Res. 1993, 26, 198;
13. e) M. Bixon, J. Fajer, G. Feher, J. H. Freed, D. A. Gamliel, A. J. Hoff, H. Levanon, K. Möbius, R. Nechushtai, J. R. Norris, A. Scherz, J. L. Sessler, D. Stehlik, Isr. J. Chem. 1992, 32, 469.
14. a) D. Gust, T. A. Moore, Science 1989, 244, 35;
15. b) V. Balzani, F. Scandola, Supramolecular Photochemistry, Ellis Horwood, Chichester, 1991, p. 110-122.
16. a) R. W. Wagner, J. S. Lindsey, J. Am. Chem. Soc. 1994, 116, 9759;
17. b) R. W. Wagner, T. E. Johnson, J. S. Lindsey, J. Am. Chem. Soc. 1996, 118, 11166;
18. c) J. S. Hsiao, B. P. Krueger, R. W. Wagner, T. E. Johnson, J. K. Delaney, D. C. Mauzerall, G. R. Fleming, J. S. Lindsey, D. F. Bocian, R. J. Donohoe, J. Am. Chem. Soc. 1996, 118, 11 181;
19. d) F. Li, S. I. Yang, Y. Ciringh, J. Seth, C. H. Martin, D. L. Singh, D. Kim, R. R. Birge, D. F. Bocian, D. Holten, J. S. Lindsey, J. Am. Chem. Soc. 1998, 120, 10001;
20. e) A. Osuka, K. Maruyama, I. Yamazaki, N. Tamai, Chem. Phys. Lett. 1990, 165, 392;
21. f) A. L. Moore, G. Dirks, D. Gust, T. A. Moore, Photochem. Photobiol. 1980, 32, 691.
22. a) H. Dieks, J. Sobek, P. Tian, H. Kurreck, Tetrahedron Lett. 1992, 33, 5951;
23. b) J. von Gersdorff, B. Kirste, H. Kurreck, Liebigs Ann. Chem. 1993, 897;
24. c) L. Sun, J. von Gersdorff, J. Sobek, H. Kurreck, Tetrahedron 1995, 51, 3535;
25. d) M. Fuchs, J. von Gersdorff, H. Dieks, H. Kurreck, K. Möbius, T. Prisner, J. Chem. Soc. Faraday Trans. 1996, 92, 949;
26. e) H. Dieks, M. O. Senge, B. Kirste, H. Kurreck, J. Org. Chem. 1997, 62, 8666;
27. f) H. Szdinski, D. Szelinski, D. Niethammer, P. Tian, H. Kurreck, Tetrahedron 1996, 52, 8497;
28. g) K. A. Jolliffe, T. D. M. Bell, K. P. Ghiggino, S. J. Langford, M. N. Paddon-Row, Angew. Chem. 1998, 110, 960; Angew. Chem. Int. Ed. 1998, 37, 916;
29. g) K. A. Jolliffe, T. D. M. Bell, K. P. Ghiggino, S. J. Langford, M. N. Paddon-Row, Angew. Chem. 1998, 110, 960; Angew. Chem. Int. Ed. 1998, 37, 916;
30. h) H. A. Staab, R. Hauck, B. Popp, Eur. J. Org. Chem. 1998, 631;
31. i) M. S. Vollmer, F. Effenberger, T. Stümpfling, A. Hartschuh, H. Port, H. C. Wolf, J. Org. Chem. 1998, 65, 631.
32. a) F. Effenberger, H. Schlosser, P. Bäuerle, S. Maier, H. Port, H. C. Wolf, Angew. Chem. 1988, 100, 274, Angew. Chem. Int. Ed. Engl. 1988, 27, 281;
33. a) F. Effenberger, H. Schlosser, P. Bäuerle, S. Maier, H. Port, H. C. Wolf, Angew. Chem. 1988, 100, 274, Angew. Chem. Int. Ed. Engl. 1988, 27, 281;
34. b) F. Effenberger, New J. Chem. 1991, 15, 117;
35. c) N. Hell, H. Port, H. C. Wolf, H. Strobel, F. Effenberger, Chem. Phys. 1993, 176, 215;
36. d) B. Heine, E. Sigmund, H. Port, J. Mol. Electronics 1991, 7, 29;
37. e) A. G. Hyslop, M. J. Therien, Inorg. Chim. Acta 1998, 275-276, 427.
38. a) M. S. Vollmer, F. Würthner, F. Effenberger, P. Emele, D. U. Meyer, T. Stümpfig, H. Port, H. C. Wolf, Chem. Eur. J. 1998, 4, 260;
39. b) F. Würthner, M. S. Vollmer, F. Effenberger, P. Emele, D. U. Meyer, H. Port, H. C. Wolf, J. Am. Chem. Soc. 1995, 117, 8090;
40. c) P. Emele, D. U. Meyer, N. Holl, H. Port, H. C. Wolf, F. Würthner, P. Bäuerle, F. Effenberger, Chem. Phys. 1994, 181, 417; G. Hungerford, M. van der Auwerder, J.-C. Chambron, V. Heitz, J.-P. Sauvage, J.-L. Pierre, D. Zurita, Chem. Eur. J. 1999, 5, 2089.
41. c) P. Emele, D. U. Meyer, N. Holl, H. Port, H. C. Wolf, F. Würthner, P. Bäuerle, F. Effenberger, Chem. Phys. 1994, 181, 417; G. Hungerford, M. van der Auwerder, J.-C. Chambron, V. Heitz, J.-P. Sauvage, J.-L. Pierre, D. Zurita, Chem. Eur. J. 1999, 5, 2089.
42. a) R. Gompper, H.-J. Mair, K. Polborn, Synthesis 1997, 696;
43. b) R. Gompper, J. Prakt. Chem. 1994, 336, 390;
44. c) S. Brandi, R. Gompper, K. Polborn, J. Prakt. Chem. 1996, 338, 451;
45. d) R. Gompper, C. Harfmann, K. Polborn, J. Prakt. Chem. 1998, 340, 381.
46. The term is used in different ways. According to F. Müller, Top. Curr. Chem. 1983, 108, 71, the flavin unit carries two methyl groups in positions C-7 and C-8; the unsubstituted compound is named isoalloxazine. According to H. Beyer, W. Walter, Lehrbuch der Organischen Chemie, 21st ed., Thieme, Stuttgart, 1988, p. 802, the name "flavin" is used for both compounds.
47. The term is used in different ways. According to F. Müller, Top. Curr. Chem. 1983, 108, 71, the flavin unit carries two methyl groups in positions C-7 and C-8; the unsubstituted compound is named isoalloxazine. According to H. Beyer, W. Walter, Lehrbuch der Organischen Chemie, 21st ed., Thieme, Stuttgart, 1988, p. 802, the name "flavin" is used for both compounds.
48. C. J. Walker, T. W. Griffiths, FEBS Lett. 1988, 239, 259.
49. a) S. Fukuzumi, T. Tanaka in Photoinduced Electron Transfer (Eds.: M. A. Fox, M. Chanon), Elsevier, Amsterdam, 1988, part C. p. 636;
50. b) C. Walsh, Acc. Chem. Res. 1980, 13, 148;
51. c) T. C. Bruice, Acc. Chem. Res. 1980, 13, 256.
52. V. d. Berghe-Snorek, M. T. Stankovich, J. Am. Chem. Soc. 1984, 106, 3685.
53. a) J. Takeda, S. Ohta, M. Hirobe, J. Am. Chem. Soc. 1987, 109, 7677;
54. b) P. Nayar, A. M. Brun, A. Harriman, T. P. Begley, J. Chem. Soc. Chem. Commun. 1992, 395;
55. c) K. Hasharoni, H. Levanon, J. Gätschmann, H. Schubert, H. Kurreck, K. Möbius, J. Phys. Chem. 1995, 99, 7514.
56. J. H. Wang. Acc. Chem. Res. 1970, 3, 90.
57. a) D. Lloyd, H. McNab, Angew. Chem. 1976, 88, 496; Angew. Chem. Int. Ed. Engl. 1976, 15, 459;
58. a) D. Lloyd, H. McNab, Angew. Chem. 1976, 88, 496; Angew. Chem. Int. Ed. Engl. 1976, 15, 459;
59. b) R. M. Wagner, C. Jutz, Chem. Ber. 1971, 104, 2975;
60. c) H. Zeschke, S. Arndt, V. Wagner, H. Schubert, Z. Chem. 1977, 77, 293.
61. a) A. D. Adler, F. R. Longo, J. D. Finarelli, J. Goldmacher, J. Assour, L. Korsakoff, J. Org. Chem. 1967, 32, 476;
62. b) D. G. Neilson in The Chemistry of Amidines and Imidates (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1991, p. 425.
63. a) A. R. Sanger, Inorg. Nucl. Chem. Lett. 1973, 9, 351;
64. b) A. W. Cordes, R. C. Haddon, R. G. Hicks, R. T. Oackley, T. T. M. Palstra, L. F. Schneemeyer, J. V. Waszczak, J. Am. Chem. Soc. 1992, 114, 5000; R. T. Boere, R. T. Oackley, R. W. Reed, J. Organomet. Chem. 1987, 331, 161.
65. b) A. W. Cordes, R. C. Haddon, R. G. Hicks, R. T. Oackley, T. T. M. Palstra, L. F. Schneemeyer, J. V. Waszczak, J. Am. Chem. Soc. 1992, 114, 5000; R. T. Boere, R. T. Oackley, R. W. Reed, J. Organomet. Chem. 1987, 331, 161.
66. A. D. Adler, F. R. Longo, F. Kampas, J. Kim, J. Inorg. Nucl. Chem. 1970, 32, 2443.
67. F. Yoneda, K. Shinozuka, K. Tsukuda, A. Koshiro, J. Heterocyclic Chem. 1979, 16, 1365.
68. A. C. Schnock, Ph.D. Thesis, Universität München, 1995.
69. -3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-115670. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
70. a) D. Lloyd, H. McNab, Angew. Chem. 1976, 88, 496;
71. b) B. W. Matthews, R. E. Stenkamp, P. M. Colman, Acta Crystallogr. 1973, B 29, 449.
72. J. Kucera, Z. Arnold, Coll. Czech. Chem. Commun. 1967, 32, 1704.
73. A. Parusel, J. Mol. Model. 1998, 4, 366.
74. M. Gouterman, G. H. Wagniere, L. C. Snyder, J. Mol. Spectrosc. 1963, 11, 108.
75. C. J. F. Böttcher, In Theory of electric polarisation, Vol. I., Elsevier, Amsterdam, 1973, p. 153.
76. D. Majumdar, R. Sen, K. Bhattacharyya, S. P. Bhattacharyya, J. Phys. Chem. 1991, 95, 4324.
77. M. Gouterman, In The Porphyrins, Vol. III, Physical Chemistry, Part B (Ed.: D. Dolphin), Academic Press, NY, 1978, p. 1.
78. a) C. El Hanine-Lmoumene, L. Lindqvist, Photochem. Photobiol. 1997, 66, 591;
79. b) I. Carmichael, G. L. Hug, J. Phys. Chem. Ref. Data 1986, 15, 1.
80. a) R. A. Marcus, J. Chem. Phys. 1989, 93, 3078;
81. b) I. R. Gould, S. Farid, R. H. Young, J. Photochem. Photobiol. A 1992, 65, 133;
82. c) G. Köhler, K. Rechthaler, G. Grabner, R. Lubodradzki, K. Suwinska, K. Rotkiewicz, J. Phys. Chem. A 1997, 101, 8518.
83. G. Nübel, W. Pfleiderer, Chem. Ber. 1962, 95, 1605.
84. H. Salkowski, Chem. Ber. 1895, 28, 1917.
85. G. Rauhut, A. Alex, J. Chandrasekhar, T. Steinke, W. Sauer, B. Beck, M. Hutter, P. Gedeck, T. Clark. VAMP 6.1. Oxford Molecular, Oxford, 1997.
86. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3402.
87. T. Clark, J. Chandrasekhar, Isr. J. Chem. 1993, 33, 435.
88. H. Lanig, R. König, T. Clark, TRAMP 1.1b, Erlangen, 1995.
89. G. Köhler, J. Photochem. 1986, 35, 189.
90. G. Köhler, K. Rotkiewicz, Spectrochim. Acta 1986, A 42, 1127.
91. G. Köhler, P. Wolschann, J. Chem. Soc. Faraday Trans. II, 1987, 83, 513.
92. G. Grabner, N. Getoff, T. Gantchev, D. Angelov, M. Shopova, Photochem. Photobiol. 1991, 54, 673.