Off the back or on the side: Comparison of meso and 2-substituted donor-acceptor difluoroborondipyrromethene (bodipy) dyads

European Journal of Organic Chemistry

Volumn , Issue 15, 2010, Pages 2867-2877

  Benniston, Andrew C ^a   Copley, Graeme ^a   Lenimetyinen, Helge ^b   Tkachenko, Nikolai V ^b  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

^b TAMPERE UNIVERSITY OF TECHNOLOGY   (Finland)

Author keywords

Dyes; Electrochemistry; Electron transfer; Fluorescence; Luminescence; Photochemistry

Indexed keywords

EID: 77952152367     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000215     Document Type: Article

References (78)

1. For comprehensive reviews see: a) A. Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891-4932;
2. b) TE. Wood, A. Thompson, Chem. Rev. 2007, 707, 1831-1861;
3. c) G. Ulrich, R. Ziessel, A. Harriman, Angew. Chem. Int. Ed. 2008, 47, 1184-1201;
4. d) R. Ziessel, G. Ulrich, A. Harriman, New J. Chem. 2007, 31, 496-501;
5. e) K. Burgess, L. Wu, Chem. Commun. 2008, 4933-4935;
6. f) M. Shah, K. Thangraj, M. L. Soong, L. Wolford, J. H. Boyer, I. R. Pollitzer, T. G. Pavlopoulos, Heteroat. Chem. 1990, 1, 389-399;
7. g) A. Burghart, H. Kim, M. B. Welch, L. H. Thoresnsen, J. Reibenspies, K. Burgess, J. Org. Chem. 1999, 64, 7813-7819.
8. For a selection of examples see: a) M. D. Yilmaz, A. Bozdemir, E. U Akkaya, Org. Lett. 2006, 8, 2871-2873;
9. b) ILY Lee, D. R. Bae, J. C. Park, H. Song, W. S. Han, J. H. Jung, Angew. Chem. Int. Ed. 2009, 48, 1239-1243;
10. c) K. Umezawa, A. Matsui, Y. Nakmura, D. Citterio, K. Suzuki, Chem. Eur. J. 2009, 75, 1096-1106;
11. d) K. Rurack, M. Kollmannsberger, J. Daub, Angew. Chem. Int. Ed. 2001, 40, 385-387;
12. e) M. M. Sartin, F. Camerel, R. Ziessel, A. J. Bard, J. Phys. Chem. C 2008, 112, 10833-10841;
13. f) R. Guliyez, O. Buyukcakir, F. Sozman, O. A. Bozdemir, Tetrahedron Lett. 2009, 50, 5139-5141.
14. A. C. Benniston, G. Copley, Phys. Chem. Chem. Phys. 2009, 11, 4124-4131.
15. a) W. Qin, M. Baruah, W. M De Borggraeve, N. Boens, J. Photochem. Photobiol. 2006, 183, 190-197;
16. b) C. N. Baki, E. U. Akkaya, J. Org. Chem. 2005, 70, 4152-4157.
17. a) D. P. Kennedy, C. M. Kormos, S. C. Burdette, J. Am. Chem. Soc. 2009, 131, 8578-8586;
18. b) X. Zhang, H.-S. Zhang, Spec. Chim. Acta 2005, 61, 1045-1049;
19. c) T. Matsumoto, Y. Urano, T Shoda, H. Kojima, T. Nagano, Org. Lett. 2007, 9, 3375-3377;
20. d) X. Peng, J. Du, J. Fan, J. Wang, Y. Wu, J. Zhao, S. Sun, T. J. Xu, J. Am. Chem. Soc. 2007, 129, 1500-1501;
21. e) A. Coskun, M. D. Yilmaz, E. U. Akkaya, Org. Lett. 2007, 9, 607609;
22. f) M. Baruah, W Qin, R. A. L. Vallée, D. Beljonne, T. Rohand, W Dehaen, N. Boens, Org. Lett. 2005, 7, 4377-4380;
23. g) J.-P. Malval, I. Leray, B. Valeur, New J. Chem. 2005, 29, 1089-1094.
24. R. Ziessel, G. Ulrich, A. Harriman, M. A. H. Alamiry, B. Stewart, P. Retailleau, Chem. Eur. J. 2009, 15, 1359-1369.
25. a) Z.-N. Sun, F-Q. Liu, Y. Chen, P. K. H. Tam, D. Yang, Org. Lett. 2008, 10, 2171-2174;
26. b) Y. Yamada, Y. Tomiyama, A. Morita, M. Ikekita, S. Aoki, ChemBioChem 2008, 9, 853-856.
27. A. Gomes, E. Fernades, J. L. F. C. Lima, J. Biochem. Biophys. Methods 2005, 65, 45-80.
28. A. C. Benniston, G. Copley, K. J. Elliott, R. W. Harrington, W. Clegg, Eur. J. Org. Chem. 2008, 2705-2713.
29. a) Z. Dost, S. Atilgan, E. U. Akkaya, Tetrahedron 2006, 62, 8484-8488;
30. b) D. Zhang, Y. Wen, Y. Xiao, G. Yu, Y. Liu, X. X. Qian, Chem. Commun. 2008, 4777-4779.
31. a) J. L. Sessler, M. R. Johnson, S. E. Creager, J. C. Fettinger, J. A. Ibers, J. Am. Chem. Soc. 1990, 772, 9310-.-9329;
32. b) J. L. Sessler, V. L. Capuano, A. Harriman, J. Am. Chem. Soc. 1993, 115, 4618-4628.
33. H. D. Tabb, K. M. Smith, J. Org. Chem. 1984, 49, 1870-1875.
34. G. B. Marini-Bettolo, O. A. Polla, J. H. Abril, Gazz. Chim. Ital. 1950, 80, 76-84.
35. N. Miyaura, K. Yamada, A. Suzuki, Tetrahedron Lett. 1979, 36, 3437-3440.
36. The molecular structures can be viewed at the website http:// www.ncl.ac.uk/mpl, or alternatively they are presented in G. Copley, PhD Thesis, Newcastle University, 2009.
37. M. Bröring, R. Krüger, S. Link, C. Kleeberg, S. Köhler, X. Xie, B. Ventura, L. Flamigni, Chem. Eur. J. 2008, 14, 2976-2983.
38. Molar volumes were calculated using data taken from: A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
39. T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. Garcia, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657-3658.
40. In order to isolate the diastereoisomers no rotation of the appended group can take place in solution at ambient temperature. Very hindered rotation would be more probable using a large bulky chiral hydroxy protecting group starting from, for example, l-bromomethyl-(+)-cuparene.
41. a) Y. Zhou, Y. Xiao, D. Li, M. Fu, X. Qian, J. Org. Chem. 2008, 73, 1571-1574;
42. b) J. Chen, A. Burghart, A. DerecskeiKovacs, K. Burgess, J. Org. Chem. 2000, 65, 2900-2906.
43. a) J. Bañuelos, F. L. Arbeloa, V. M. Martínez, T. A. López, I. L. Arbeloa, Phys. Chem. Chem. Phys. 2004, 6, 4247-4253;
44. b) J. B. Prieto, F. L. Arbeloa, V. M. Martínez, I. L. Arbeloa, Chem. Phys. 2004, 296, 13-22.
45. C.-W. Wan, A. Burghart, J. Chen, F. Bergström, L. B.-Å. Johansson, M. F. Wollbrd, T. G. Kim, M. R. Topp, R. M. Hochstrasser, K. Burgess, Chem. Eur. J. 2003, 9, 4430-4441.
46. S. J. Strickler, R. A. Berg, J. Chem. Phys. 1962, 37, 814-822.
47. J. H. Boyer, A. M. Haag, G. Sathyamoorthi, M.-L. Soong, K. Thangaraj, T. G. Pavlopoulos, Heteroat. Chem. 1993, 4, 39-49.
48. R. Englman, J. Jortner, Mol. Phys. 1970, 18, 145-164.
49. F. Bergström, I. Mikhalyov, R. Hägglöf, R. Wortmann, T. Ny, L. B.-Å. Johansson, J. Am. Chem. Soc. 2002, 124, 196-204.
50. a) T. Rohand, J. Lycoops, S. Smout, E. Braeken, M. Sliwa, M. Van der Auweraer, W. Dehaen, W. M. De Borggraeve, N. Boens, Photochem. Photobiol. Sci. 2007, 6, 1061-1066;
51. b) W. Qin, T. Rohand, M. Baruah, A. Stefan, M. Van der Auweraer, W. Dehaen, N. Boens, Chem. Phys. Lett. 2006, 420, 562-568;
52. c) W. Qin, M. Baruah, M. Van der Auweraer, F. C. De Schryver, N. Boens, J. Phys. Chem. A 2005, 109, 7371-7384;
53. d) W. Qin, M. Baruah, A. Stefan, M. Van der Auweraer, N. Boens, ChemPhysChem 2005, 6, 2343-2351.
54. A single mono-exponential decay is not always observed and is often associated with other processes stemming from, the excited-state such as vibrational cooling, proton transfer etc., see for example:
55. H. Wang, H. Zhang, O. K. Abou-Zied, C. Yu, F. E. Romesberg, M. Glasbeek, Chem. Phys. Lett. 2003, 367, 599-608.
56. G. Duvanel, N. Banerji, E. Vauthey, J. Phys. Chem. A 2007, 111, 5361-5369.
57. S. Hattori, K. Ohkubo, Y. Urano, H. Sunhara, T. Nagano, Y. Wada, N. V. Tkachenko, H. Lemmetyinen, S. Fukuzumi, J. Phys. Chem. B 2005, 109, 15368-15375.
58. a) P.P. Lainé, F. Bedioui, F. Loiseau, C. Chiorboli, S. Campagna, J. Am. Chem. Soc. 2006, 128, 7510-7521;
59. b) K. Nomoto, S. Kume, H. Nishihara, J. Am. Chem. Soc. 2009, 131, 3830-3831.
60. W. B. Davis, M. A. Ratner, M. R. Wasielewski, J. Am. Chem. Soc. 2001, 123, 7877-7886.
61. R. A. Marcus, Discuss. Faraday Soc. 1960, 29, 21-31.
62. a) P. L. Dutton, J. S. Leight, M. Seibert, Biochem. Biophys. Res. Commun. 1972, 46, 406-413;
63. b) M. C. Thuranauer, J. J. Katz, J. R. Norris, Proc. Natl. Acad, Sci. USA 1975, 72, 3270-3274;
64. c) K. Hasharoni, H. Levanon, S. R. Greenfield, D. J. Gosztola, W. A. Svec, M. R. Wasielewski, J. Am. Chem. Soc, 1995, 117, 8055-8056;
65. d) M. R. Wasielewski, D. W Minsek, M. P. Niemczyk, W. A. Svec, N. C. Yang, J. Am. Chem. Soc. 1990, 112, 2823-2824;
66. e) J. Hu, B. Xia, D. Bao, A. Ferreira, J. Wan, G. Jones II, V. I. Vullev, J. Phys. Chem. A 2009, 113, 3096-3107.
67. a) M. Bixon, J. Jortner, Adv. Chem. Phys. 1999, 106, 35-208;
68. b) J. Kroon, H. Oevering, J. W. Verhoeven, J. M. Warman, A. M. Oliver, M. N. Paddon-Row, J. Phys. Chem. 1993, 97, 5065-5069;
69. c) K. J. Smit, J. M. Warman, M. P. de Haas, M. N. Paddon-Row, A. M. Oliver, Chem. Phys. Lett. 1988, 152, 177-182;
70. d) N. Liang, J. R. Miller, G. L. Closs, J. Am. Chem, Soc. 1990, 112, 5353-5354.
71. a) S. Franzen, J. Martin, Annu. Rev. Phys. Chem. 1995, 46, 453-487;
72. b) A. C. Benniston, G. M. Chapman, A. Harriman, M. Mehrabi, J. Phys. Chem. A 2004, 108, 9026-9036.
73. A. A. Gorman, I. Hamblett, T. A. King, M. D. Rahn, J. Photochem. Photobiol. A: Chem. 2000, 130, 127-132.
74. N. Yoshida, T. Ishizuka, K. Yofu, M. Murakami, H. Miyasaka, T. Okada, Y. Nagata, A. Itaya, H. S. Cho, D. Kim, A. Osuka, Chem. Eur. J. 2003, 9, 2854-2866.
75. NR assuming all other parameters remain constant. This argument has been used to explain the rapid non-radiative deactivation of a charge-transfer state in a N-H-containing Bodipy-based tripartite array, see:
76. M. A. H. Alamiry, A. Harriman, L. J. Mallon, G. Ulrich, R. Ziessel, Eur. J. Org. Chem. 2008, 2774-2782.
77. R. I. Cukier, D. G. Nocera, Annu. Rev. Chem. 1998, 49, 337-369.
78. A. C. Benniston, G. Copley, H. Lemmetyinen, N. V. Tkachenko, ChemPhysChem 2010, in press.