BF2-chelate complexes of 6-(4-iodophenyl)-2,3,4,8,9,10- hexamethyldipyrrin and 2-(4-iodobenzoyl)-3,4,5-trimethylpyrrole: Fluorescent dyes with a chemical anchor group

Zeitschrift fur Anorganische und Allgemeine Chemie

Volumn 634, Issue 9, 2008, Pages 1555-1559

  Bröring, Martin ^a   Krüger, Robin ^a   Kleeberg, Christian ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

BODIPY s; Boron; Fluorescent dyes; Oligopyrroles; Structure function correlation

Indexed keywords

EID: 53949108344     PISSN: 00442313     EISSN: 15213749     Source Type: Journal    
DOI: 10.1002/zaac.200800112     Document Type: Article

References (56)

1. T. E. Wood, A. Thompson, Chem. Rev. 2007, 107, 1831-1861.
2. T. Chen, J. H. Boyer, M. L. Trudell, Heteroatom Chem. 1997, 8, 51-54.
3. G. Sathyamoorthi, L. T. Wolford, A. M. Haag, J. H. Boyer, Heteroatom Chem. 1994, 5, 245-249.
4. F. Li, S. I. Yang, Y. Ciringh, J. Seth, C. H. Martin III, D. L. Singh, D. Kim, R. R. Birge, D. F. Bocian, D. Holten, J. S. Lindsey, J. Am. Chem. Soc. 1998, 120, 10001-10017.
5. R. K. Lammi, A. Amboise, T. Balasubramanian, R. W. Wagner, D. F. Bocian, D. Holten, J. S. Lindsey, J. Am. Chem. Soc. 2000, 122, 7579-7591.
6. A. Amboise, C. Kirmaier, R. W. Wagner, R. S. Loewe, D. F. Bocian, D. Holten, J. S. Lindsey, J. Org. Chem. 2002, 67, 3811-3826.
7. T. A. Golovkova, D. V. Kozlov, D. C Neckers, J. Org. Chem. 2005, 70, 5545-5549.
8. R. P. Haugland, in Handbook of Molecular Probes and Research Products, Molecular Probes, Inc., Eugene, OR, 9th edn, 2002.
9. R. W. Wagner, J. S. Lindsey, Pure Appl. Chem. 1996, 68, 1373-1380.
10. G. Beer, K. Rurack, J. Daub, Chem. Commun. 2001, 1138-1139.
11. G. Beer, C. Niederalt, S. Grimme, J. Daub, Angew. Chem. 2000, 110, 3385-3388;
12. Angew. Chem. Int. Ed. 2000, 39, 3252-3255.
13. M. Kollmannsberger, K. Rurack, U. Resch-Genger, W. Rettig, J. Daub, Chem. Phys. Lett. 2000, 329, 363-369.
14. F. Sancenon, R. Martinez-Manez, J. Soto, Angew. Chem. 2002, 112, 1474-1477;
15. Angew. Chem. Int. Ed. 2002, 41, 1416-1419.
16. Y. Gabe, Y. Urano, K. Kikuchi, H. Kojima, T. Nagano, J. Am. Chem. Soc. 2004, 126, 3357-3367.
17. T. Ueno, Y. Urano, H. Kojima, T. Nagano, J. Am. Chem. Soc. 2006, 128, 10640-10641.
18. Y. Mei, P. A. Bentley, W. Wang, Tetrahedron Lett. 2006, 47, 2447-2449.
19. N. Basaric, M. Baruah, W. Qin, B. Metten, M. Smet, W. Dehaen, N. Boens, Org. Biomol. Chem. 2005, 3, 2755-2761.
20. C. McCusker, J. B. Carroll, V. M. Rotello, Chem. Commun. 2005, 996-998.
21. R. Y. Lai, A. J. Bard, J. Phys. Chem. B 2003, 107, 5036-5042.
22. J. M. Brom, Jr., J. L. Langer, J. Alloys Compd. 2002, 338, 112-115.
23. A. Hepp, G. Ulrich, R. Schmechel, H. von Seggern, R. Ziessel, Synth. Met. 2004, 146, 11-15.
24. S. Hattori, K. Ohkubo, Y. Urano, H. Sunahara, T. Nagano, Y. Wada, N. V. Tkchanko, H. Lemmetyinen, S. Fukuzumi, J. Phys. Chem. B 2005, 109, 15368-15375.
25. M. P. Debreczeny, W. A. Svec, M. R. Wasielewski, Science 1996, 274, 584-587.
26. Y. Teki, H. Tamekuni, J. Takeuchi, Y. Miura, Angew. Chem. 2006, 116, 4782-4786;
27. Angew. Chem. Int. Ed. 2006, 45, 4666-4670.
28. R. Ziessel, G. Ulrich, A. Harriman, New J. Chem. 2007, 31, 496-501.
29. A. Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891-4932.
30. F. Bergstroem, I. Mikhalyov, P. Haeggloef, R. Wortmann, T. Ny, L. B.-A ̊. Johansson, J. Am. Chem. Soc. 2002, 124, 196-204.
31. I. Mikhalyov, N. Gretskaya, F. Bergstroem, L. B.-A. Johansson, Phys. Chem. Chem. Phys. 2002, 4, 5663-5670.
32. D. Marushchak, S. Kalinin, I. Mikhalyov, N. Gretskaya, L. B.-Å. Johansson, Spectrochim. Acta 2006, 65A, 113-122.
33. M. Bröring, D. Griebel, C. Hell, A. Pfister, J. Porphyrins Phthalocyanines 2001, 5, 708-714.
34. M. Bröring, Synthesis 2000, 1291-1294.
35. Y. Zhang, A. Thompson, S. J. Rettig, D. Dolphin, J. Am. Chem. Soc. 1998, 120, 13537-13538.
36. H. S. Gill, I. Finger, I. Bozidarevic, F. Szydlo, M. J. Scott, New J. Chem. 2005, 29, 68-71.
37. M. Bröring, S. Link, C. D. Brandt, E. Cónsul Tejero, Eur. J. Inorg. Chem. 2007, 1661-1670.
38. M. Bröring, E. Cónsul-Tejero, J. Organomet. Chem. 2005, 690, 5290-5299.
39. M. Bröring, C. D. Brandt, E. Cónsul-Tejero, Z. Anorg. Allg. Chem. 2005, 631, 1793-1798.
40. M. Bröring, C. D. Brandt, J. Bley-Escrich, J.-P. Gisselbrecht, Eur. J. Inorg. Chem. 2002, 910-917.
41. M. Bröring, C. D. Brandt, J. Lex, H.-U. Humpf, J. Bley-Escrich, J.-P. Gisselbrecht, Eur. J. Inorg. Chem. 2001, 2549-2556.
42. M. Bröring, S. Köhler, S. Link, O. Burghaus, C. Pietzonka, H. Kelm, H.-J. Krüger, Chem. Eur. J. 2008, 14, 4006-4016.
43. M. Bröring, R. Krüger, S. Link, C. Kleeberg, S. Köhler, X. Xie, B. Ventura, L. Flamigni, Chem. Eur. J. 2008, 14, 2976-2983.
44. 4-Haloaryl groups have been used for similar purposes, see e.g.: (a) A. Burghart, H. Kim, M. B. Welch, L. H. Thoresen, J. Reibenspies, K. Burgess, F. Bergstroem, L. B.-Å. Johansson, J. Org. Chem. 1999, 64, 7813-7819;
45. (b) M. Bröring, M. Cordes, S. Köhler, Z. Anorg. Allg. Chem. 2008, 634, 125-130.
46. J. Chen, A. Burghart, C.-W. Wan, L. Thai, C. Ortiz, J. Reibenspies, K. Burgess, Tetrahedron Lett. 2000, 41, 2303-2307.
47. F. B. Mallory, C. W. Mallory, Encyclopedia of Nuclear Magnetic Resonance, Wiley, New York, 1996.
48. F. B. Mallory, C. W. Mallory, W. M. Ricker, J. Org. Chem. 1985, 50, 457-461.
49. K. L. Servis, K.-N. Fang, J. Am. Chem. Soc. 1968, 90, 6712-6717.
50. J. Chen, J. Reibenspies, A. Derecskei-Kovacs, K. Burgess, Chem. Commun. 1999, 2501-2502.
51. M. Kasha, H. R. Rawls, M. A. El-Bayoumi, Pure Appl. Chem. 1965, 11, 371-392.
52. F. R. Lipset, Prog. Dielectr. 1967, 7, 217.
53. A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
54. A. Treibs, D. Dinelli, Liebigs Ann. Chem. 1935, 517, 152-169.
55. G. M. Sheldrick, SHELXS-97, Program for Structure Determination, University of Göttingen, Göttingen, Germany, 1997.
56. G. M. Sheldrick, SHELXL-97, Program for Structure Refinement, University of Göttingen, Göttingen, Germany, 1997.