Aggregation effects in visible-light flavin photocatalysts: Synthesis, structure, and catalytic activity of 10-arylflavins

Chemistry - A European Journal

Volumn 19, Issue 3, 2013, Pages 1066-1075

  Daďová, Jitka ^a,b   Kümmel, Susanne ^a   Feldmeier, Christian ^a   Cibulková, Jana ^b   Pažout, Richard ^b   Maixner, Jaroslav ^b   Gschwind, Ruth M ^a   König, Burkhard ^a   Cibulka, Radek ^b  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

aggregation; flavins; noncovalent interactions; organocatalysis; oxidation; photocatalysis

Indexed keywords

AERIAL OXIDATION; ALCOHOL OXIDATION; ARYL RINGS; CRYSTALLINE PHASE; FLAVIN CHROMOPHORES; FLAVINS; HIGHER EFFICIENCY; MODEL REACTIONS; NON-COVALENT INTERACTION; ORGANOCATALYSIS; VISIBLE LIGHT;

AGGLOMERATION; ALDEHYDES; CHROMOPHORES; HYDROGEN BONDS; PHOTOCATALYSIS; QUANTUM YIELD; REACTION KINETICS; SYNTHESIS (CHEMICAL);

OXIDATION;

RIBOFLAVIN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; LIGHT; PHOTOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; FLAVINS; LIGHT; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOTOCHEMICAL PROCESSES;

EID: 84872173334     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201202488     Document Type: Article

References (107)

1. Chemistry and Biochemistry of Flavoenzymes (Ed.:, F. Müller,), CRC, Boca Raton, 1991
2. B. Palfey, V. Massey, in Comprehensive Biological Catalysis Vol. 3 (Ed.:, M. Sinnott,), Academic Press, London, 1998, pp. 83-154
3. V. Massey, Biochem. Soc. Trans. 2000, 28, 283-296
4. S. Ghisla, V. Massey, Eur. J. Biochem. 1989, 181, 1-17.
5. F. G. Gelalcha, Chem. Rev. 2007, 107, 3338-3361
6. Y. Imada, T. Naota, Chem. Rec. 2007, 7, 354-361.
7. V. Mojr, M. Buděšínský, R. Cibulka, T. Kraus, Org. Biomol. Chem. 2011, 9, 7318
8. Y. Imada, T. Kitagawa, T. Ohno, H. Iida, T. Naota, Org. Lett. 2010, 12, 32-35
9. R. Jurok, R. Cibulka, H. Dvořáková, F. Hampl, J. Hodačová, Eur. J. Org. Chem. 2010, 5217-5224
10. V. Mojr, V. Herzig, M. Buděšínský, R. Cibulka, T. Kraus, Chem. Commun. 2010, 46, 7599-7601
11. J. Žurek, R. Cibulka, H. Dvořáková, J. Svoboda, Tetrahedron Lett. 2010, 51, 1083-1086
12. C. Smit, M. W. Fraaije, A. J. Minnaard, J. Org. Chem. 2008, 73, 9482-9485
13. J. Piera, J.-E. Bäckvall, Angew. Chem. 2008, 120, 3558-3576
14. Angew. Chem. Int. Ed. 2008, 47, 3506-3523
15. L. Baxová, R. Cibulka, F. Hampl, J. Mol. Catal. A 2007, 277, 53-60
16. M. Lindén, M. Johansson, N. Hermanns, J.-E. Bäckvall, J. Org. Chem. 2006, 71, 3849-3853
17. Y. Imada, H. Iida, S. Ono, Y. Masui, S.-I. Murahashi, Chem. Asian J. 2006, 1-2, 136-147
18. Y. Imada, H. Iida, T. Naota, J. Am. Chem. Soc. 2005, 127, 14544-14545
19. Y. Imada, H. Iida, S.-I. Murahashi, T. Naota, Angew. Chem. 2005, 117, 1732-1734
20. Angew. Chem. Int. Ed. 2005, 44, 1704-1706
21. A. A. Lindén, N. Hermanns, S. Ott, L. Krüger, J.-E. Bäckvall, Chem. Eur. J. 2005, 11, 112-119
22. Y. Imada, H. Iida, S. Ono, S.-I. Murahashi, J. Am. Chem. Soc. 2003, 125, 2868-2869
23. S. I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474
24. Angew. Chem. Int. Ed. 2002, 41, 2366-2368
25. A. B. E. Minidis, J.-E. Bäckvall, Chem. Eur. J. 2001, 7, 297-302
26. C. Mazzini, J. Lebreton, R. Furstoss, J. Org. Chem. 1996, 61, 8-9
27. S.-I. Murahashi, T. Oda, Y. Masui, J. Am. Chem. Soc. 1989, 111, 5002-5003.
28. Comprehensive Series in Photochemical & Photobiological Sciences (Eds.:, E. Silva, A.M. Edwards,), Vol. 6, RSC Publishing, Cambridge, 2006.
29. U. Megerle, M. Wenninger, R.-J. Kuta, R. Lechner, B. König, B. Dick, E. Riedle, Phys. Chem. Chem. Phys. 2011, 13, 8869-8880
30. H. Schmaderer, P. Hilgers, R. Lechner, B. König, Adv. Synth. Catal. 2009, 351, 163-174
31. J. Svoboda, H. Schmaderer, B. König, Chem. Eur. J. 2008, 14, 1854-1865
32. R. Cibulka, R. Vasold, B. König, Chem. Eur. J. 2004, 10, 6223-6231
33. M. Yasuda, T. Nakai, Y. Kawahito, T. Shiragami, Bull. Chem. Soc. Jpn. 2003, 76, 601-605
34. V. T. D'Souza, Supramol. Chem. 2003, 15, 221-229
35. S. Fukuzumi, K. Yasui, T. Suenobu, K. Ohkubo, M. Fujitsuka, O. Ito, J. Phys. Chem. A 2001, 105, 10501-10510
36. S. Fukuzumi, S. Kuroda, Res. Chem. Intermed. 1999, 25, 789-811
37. W. Tong, H. Ye, H. Zhu, V. T. D'Souza, J. Mol. Struct. 1995, 19-27
38. S. Fukuzumi, K. Tanii, T. Tanaka, J. Chem. Soc. Chem. Commun. 1989, 816-818
39. S. Fukuzumi, S. Kuroda, T. Tanaka, J. Am. Chem. Soc. 1985, 107, 3020-3027.
40. J.-M. Kim, M. A. Bogdan, P. S. Mariano, J. Am. Chem. Soc. 1993, 115, 10591-10595.
41. R. Lechner, S. Kümmel, B. König, Photochem. Photobiol. Sci. 2010, 9, 1367-1377.
42. W. A. Massad, Y. Barbieri, M. Romero, N. A. Garcia, Photochem. Photobiol. 2008, 84, 1201-1208.
43. J. García, E. Silva, J. Nutr. Biochem. 1997, 8, 341-345.
44. C. B. Martin, M.-L. Tsao, C. M. Hadad, M. S. Platz, J. Am. Chem. Soc. 2002, 124, 7226-7234.
45. K. Huvaere, D. R. Cardoso, P. Homem-de-Mello, S. Westermann, L. H. Skibsted, J. Phys. Chem. B 2010, 114, 5583-5593
46. O. Lu, G. Bucher, W. Sander, ChemPhysChem 2004, 5, 47-56.
47. E. Silva, A. M. Edwards, D. Pacheco, J. Nutr. Biochem. 1999, 10, 181-185.
48. K. Tatsumi, H. Ichikawa, S. Wada, J. Contam. Hydrol. 1992, 9, 207-219.
49. R. Lechner, B. König, Synthesis 2010, 1712-1718.
50. E. Sikorska, M. Sikorski, R. P. Steer, F. Wilkinson, D. R. Worrall, J. Chem. Soc. Faraday Trans. 1998, 94, 2347-2353
51. E. Sikorska, I. Khmelinskii, A. Komasa, J. Koput, L. F. V. Ferreira, J. R. Herance, J. R. Bourdelande, S. L. Williams, D. R. Worrall, M. Insińska-Rak, M. Sikorski, Chem. Phys. 2005, 314, 239-247.
52. J. Daďová, E. Svobodová, M. Sikorski, B. König, R. Cibulka, ChemCatChem 2012, 4, 620-623.
53. S. Fukuzumi, K. Tanii, T. Tanaka, J. Chem. Soc. Perkin Trans. 2 1989, 2103-2108
54. J. N. Chaon, G. R. Jamieson, R. S. Sinclair, Chem. Phys. Lipids 1987, 43, 81-99.
55. U. Megerle, R. Lechner, B. König, E. Riedle, Photochem. Photobiol. Sci. 2010, 9, 1400-1406.
56. N. A. McDonald, C. Subramani, S. T. Caldwell, N. Y. Zainalabdeen, G. Cooke, V. M. Rotello, Tetrahedron Lett. 2011, 52, 2107-2110
57. S. T. Caldwell, G. Cooke, S. H. Hewage, S. Mabruk, G. Rabani, V. Rotello, B. O. Smith, C. Subramani, P. Woisel, Chem. Commun. 2008, 4126-4128
58. S.-Y. Ju, F. Papadimitrakopoulos, J. Am. Chem. Soc. 2008, 130, 655-664
59. S. M. Butterfield, C. M. Goodman, V. M. Rotello, M. L. Waters, Angew. Chem. 2004, 116, 742-745
60. Angew. Chem. Int. Ed. 2004, 43, 724-727
61. M. Gray, A. J. Goodman, J. B. Carroll, K. Bardon, M. Markey, G. Cooke, V. M. Rotello, Org. Lett. 2004, 6, 385-388
62. J. L. Pellett, D. F. Becker, A. K. Saenger, J. A. Fuchs, M. T. Stankovich, Biochemistry 2001, 40, 7720-7728
63. A. Niemz, V. M. Rotello, Acc. Chem. Res. 1999, 32, 44-52
64. H. A. Staab, J. Kanellakopulos, P. Kirsch, C. Krieger, Liebigs Ann. 1995, 1827-1836.
65. E. C. Breinlinger, C. J. Keenan, V. M. Rotello, J. Am. Chem. Soc. 1998, 120, 8606-8609.
66. F. Collard, R. L. Fagan, J. Zhang, I. Nemet, B. A. Palfey, V. M. Monier, Biochemistry 2011, 50, 7977-7986
67. C. Estarellas, A. Frontera, D. Quiñonero, P. M. Deyà, Chem. Asian J. 2011, 6, 2316-2318.
68. R. Drabent, H. Grajek, Biochim. Biophys. Acta Gen. Subj. 1983, 758, 98-103.
69. F. Yoneda, K. Shinozuka, K. Tsukuda, J. Heterocycl. Chem. 1979, 16, 1365-1367.
70. M. Insińska-Rak, E. Sikorska, J. L. Bourdelande, I. V. Khmelinskii, W. Prukala, K. Dobek, J. Karolczak, I. F. Machado, L. F. V. Ferreira, E. Dulewicz, A. Komasa, D. R. Worrall, M. Kubicki, M. Sikorski, Photochem. Photobiol. A, Chemistry 2007, 186, 14-23
71. M. Á. Farrán, R. M. Claramunt, C. Lopéz, E. Pinilla, M. R. Torres, J. Elguero, ARKIVOC (Gainesville, FL, U.S.) 2007, 4, 20-38
72. M. Insińska-Rak, E. Sikorska, J. R. Herance, J. L. Bourdelande, I. V. Khmelinskii, M. Kubicki, W. Prukala, I. F. Machado, A. Komasa, L. F. V. Ferreira, M. Sikorski, Photochem. Photobiol. Sci. 2005, 4, 463-468
73. M. Ebitani, Acta Crystallogr. Sect. B 1993, 49, 136-144
74. M. Wang, C. J. Fritchie, Acta Crystallogr. Sect. B 1973, 29, 2040-2045
75. M. vonGlehn, R. Norrestam, Acta Chem. Scand. 1972, 26, 1490-1502.
76. S. Shinkai, S. Kawanabe, A. Kawase, T. Yamaguchi, O. Manabe, S. Harada, H. Nakamura, N. Kasai, Bull. Chem. Soc. Jpn. 1988, 61, 2095-2102.
77. A. Macchioni, G. Ciancaleoni, C. Zuccaccia, D. Zuccaccia, Chem. Soc. Rev. 2008, 37, 479-489.
78. P. R. Schreiner, L. V. Chernish, P. A. Gunchenko, E. Y. Tikhonchuk, H. Hausmann, M. Serafin, S. Schlecht, J. E. P. Dahl, R. M. K. Carlson, A. A. Fokin, Nature 2011, 477, 308-311.
79. C. A. Hunter, Angew. Chem. 2004, 116, 5424-5439
80. Angew. Chem. Int. Ed. 2004, 43, 5310-5324.
81. E. Sikorska, I. V. Khmelinskii, W. Prukala, S. L. Williams, M. Patel, D. R. Worrall, J. L. Bourdelande, J. Koput, M. Sikorski, J. Phys. Chem. A 2004, 108, 1501-1508
82. E. Sikorska, I. V. Khmelinskii, J. Koput, J. L. Bourdelande, M. Sikorski, J. Mol. Struct. 2004, 697, 137-141.
83. B. König, M. Pelka, H. Zieg, T. Ritter, H. Bouas-Laurent, R. Bonneau, J.-P. Desvergne, J. Am. Chem. Soc. 1999, 121, 1681-1687.
84. D. Rehm, A. Weller, Ber. Bunsen-Ges. Phys. Chem. 1969, 73, 834-839
85. F. Scandola, V. Balzani, G. B. Schuster, J. Am. Chem. Soc. 1981, 103, 2519-2523.
86. P. R. Ogilby, C. S. Foote, J. Am. Chem. Soc. 1983, 105, 3423-13430
87. S. R. Davidson, E. J. Pratt, Photochem. Photobiol. 1984, 40, 23-28
88. R. L. Jensen, J. Arnbjerg, P. Ogilby, J. Am. Chem. Soc. 2010, 132, 8098-8105.
89. D. D. Perrin, W. L. F. Armarego, Purification of Laboratory Chemicals, 4 th ed., Elsevier Science Ltd., Oxford, 1996.
90. D. B. McCormick, J. Heterocycl. Chem. 1970, 7, 447-450.
91. M. Mansurova, M. S. Koay, W. Gärtner, Eur. J. Org. Chem. 2008, 5401-5406.
92. J. M. Wilson, G. Henderson, F. Black, A. Sutherland, R. L. Ludwig, K. H. Vousden, D. J. Robins, Bioorg. Med. Chem. 2007, 15, 77-86.
93. B. Priewisch, K. Rück-Braun, J. Org. Chem. 2005, 70, 2350-2352.
94. Oxford Diffraction. CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, Oxfordshire (England), 2008.
95. L. Palatinus, G. Chapuis, J. Appl. Crystallogr. 2007, 40, 786-790.
96. V. Petříček, M. Dušek, L. Palatinus, Jana2006, Structure Determination Software Programs, Institute of Physics, Prague (Czech Republic), 2006.
97. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838.
98. C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, J. vandeStreek, J. Appl. Crystallogr. 2006, 39, 453-457.
99. A. Jerschow, N. Müller, J. Magn. Reson. 1997, 125, 372-375.
100. H. C. Chen, S. H. J. Chen, J. Phys. Chem. 1984, 88, 5118-5121.
101. Y. H. Zhao, M. H. Abraham, A. M. Zissimos, J. Org. Chem. 2003, 68, 7368-7373.
102. K. Schober, E. Hartmann, H. Zhang, R. M. Gschwind, Angew. Chem. 2010, 122, 2855-2859
103. Angew. Chem. Int. Ed. 2010, 49, 2794-2797.
104. H. Zhang, R. M. Gschwind, Angew. Chem. 2006, 118, 6540-6544
105. Angew. Chem. Int. Ed. 2006, 45, 6391-6394.
106. S. L. Murov, I. Carmichael, G. L. Hug, Handbook of Photochemistry, 2 nd ed ition, CRC Press, New York, 1993.
107. Origin 6.1. OriginLab Corporation, Northampton, 2000.