Bodipy dyes with tunable redox potentials and functional groups for further tethering: Preparation, electrochemical, and spectroscopic characterization

Journal of the American Chemical Society

Volumn 132, Issue 49, 2010, Pages 17560-17569

  Krumova, Katerina ^a   Cosa, Gonzalo ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION AND EMISSION SPECTRA; COMMONLY USED; ELECTROCHEMICAL CHARACTERIZATIONS; ELECTRONWITHDRAWING; ELECTROPHILES; EMISSION QUANTUM YIELD; FLUORESCENT LABELING AGENT; FLUORESCENT SENSORS; FLUOROGENIC PROBES; FORMYL GROUP; HOMO-LUMO GAPS; MOLAR EXTINCTION COEFFICIENT; NUCLEOPHILIC ATTACK; PHOTO-INDUCED ELECTRON TRANSFER; REDOX POTENTIALS; SPECTROSCOPIC CHARACTERIZATION;

DYES; EMISSION SPECTROSCOPY; METHANOL; QUANTUM YIELD; REDOX REACTIONS;

FLUOROPHORES;

DYE; ELECTROPHILE; FLUORESCENT DYE; FUNCTIONAL GROUP; NUCLEOPHILE;

ARTICLE; ELECTROCHEMISTRY; ELECTRON TRANSPORT; EMISSION TOMOGRAPHY; FLUORESCENCE; OXIDATION REDUCTION POTENTIAL; QUANTUM YIELD; SPECTROSCOPY; SYNTHESIS;

BORON COMPOUNDS; ELECTROCHEMICAL TECHNIQUES; FLUORESCENT DYES; OXIDATION-REDUCTION; SPECTROMETRY, FLUORESCENCE;

EID: 78650111171     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1075663     Document Type: Article

References (52)

1. Alfred, T. and Franz-Heinrich, K. Justus Liebigs Ann. Chem. 1968, 718, 208-223
2. Haugland, R. P. Handbook of Fluorescent Probes and Research Products, 10th ed.; Molecular Probes, Inc.: Eugene, OR, 2005.
3. Johnson, I. D., Kang, H. C., and Haugland, R. P. Anal. Biochem. 1991, 198, 228-237
4. Loudet, A. and Burgess, K. Chem. Rev. 2007, 107, 4891-4932
5. Gilles, U., Raymond, Z., and Anthony, H. Angew. Chem., Int. Ed. 2008, 47, 1184-1201
6. Wood, T. E. and Thompson, A. Chem. Rev. 2007, 107, 1831-1861
7. Ziessel, R., Ulrich, G., and Harriman, A. New J. Chem. 2007, 31, 496-501
8. Qin, W., Rohand, T., Dehaen, W., Clifford, J. N., Driesen, K., Beljonne, D., Van Averbeke, B., Van der Auweraer, M., and Boens, N. l. J. Phys. Chem. A 2007, 111, 8588-8597
9. Qin, W., Baruah, M., Van der Auweraer, M., De Schryver, F. C., and Boens, N. l. J. Phys. Chem. A 2005, 109, 7371-7384
10. Arbeloa, F. L. P., Bañuelos, J., Martínez, V., Arbeloa, T., and Arbeloa, I. L. P. Int. Rev. Phys. Chem. 2005, 24, 339-374
11. Korlach, J., Schwille, P., Webb, W. W., and Feigenson, G. W. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 8461-8466
12. Drummen, G. P. C., van Liebergen, L. C. M., Op den Kamp, J. A. F., and Post, J. A. Free Radical Biol. Med. 2002, 33, 473-490
13. Pap, E. H. W., Drummen, G. P. C., Winter, V. J., Kooij, T. W. A., Rijken, P., Wirtz, K. W. A., Op den Kamp, J. A. F., Hage, W. J., and Post, J. A. FEBS Lett. 1999, 453, 278-282
14. Lemcke, S., Hönnscheidt, C., Waschatko, G., Bopp, A., Lütjohann, D., Bertram, N., and Gehrig-Burger, K. Mol. Cell. Endocrinol. 2010, 314, 31-40
15. Singh, K. K., Parwaresch, R., and Krupp, G. RNA 1999, 5, 1348-1356
16. Danell, A. S. and Parks, J. H. Int. J. Mass Spectrom. 2003, 229, 35-45
17. Zeng, L., Miller, E. W., Pralle, A., Isacoff, E. Y., and Chang, C. J. J. Am. Chem. Soc. 2005, 128, 10-11
18. Yuan, M., Li, Y., Li, J., Li, C., Liu, X., Lv, J., Xu, J., Liu, H., Wang, S., and Zhu, D. Org. Lett. 2007, 9, 2313-2316
19. Wang, J. and Qian, X. Org. Lett. 2006, 8, 3721-3724
20. Baruah, M., Qin, W., Vallee, R. A. L., Beljonne, D., Rohand, T., Dehaen, W., and Boens, N. Org. Lett. 2005, 7, 4377-4380
21. Bozdemir, O. A., Sozmen, F., Buyukcakir, O., Guliyev, R., Cakmak, Y., and Akkaya, E. U. Org. Lett. 2010, 12, 1400-1403
22. Peng, X., Du, J., Fan, J., Wang, J., Wu, Y., Zhao, J., Sun, S., and Xu, T. J. Am. Chem. Soc. 2007, 129, 1500-1501
23. Krumova, K., Oleynik, P., Karam, P., and Cosa, G. J. Org. Chem. 2009, 74, 3641-3651
24. Oleynik, P., Ishihara, Y., and Cosa, G. J. Am. Chem. Soc. 2007, 129, 1842-1843
25. Khatchadourian, A., Krumova, K., Boridy, S., Ngo, A. T., Maysinger, D., and Cosa, G. Biochemistry 2009, 48, 5658-5668
26. Gabe, Y., Ueno, T., Urano, Y., Kojima, H., and Nagano, T. Anal. Bioanal. Chem. 2006, 386, 621-626
27. Yasuyuki, Y., Yumiko, T., Akinori, M., Masahiko, I., and Shin, A. ChemBioChem 2008, 9, 853-856
28. Sun, Z.-N., Wang, H.-L., Liu, F.-Q., Chen, Y., Tam, P. K. H., and Yang, D. Org. Lett. 2009, 11, 1887-1890
29. Andrew, C. B., Graeme, C., Kristopher, J. E., Ross, W. H., and William, C. Eur. J. Org. Chem. 2008, 2008, 2705-2713
30. Sun, Z.-N., Liu, F.-Q., Chen, Y., Tam, P. K. H., and Yang, D. Org. Lett. 2008, 10, 2171-2174
31. Gabe, Y., Urano, Y., Kikuchi, K., Kojima, H., and Nagano, T. J. Am. Chem. Soc. 2004, 126, 3357-3367
32. de Silva, A. P., Gunaratne, H. Q. N., Gunnlaugsson, T., Huxley, A. J. M., McCoy, C. P., Rademacher, J. T., and Rice, T. E. Chem. Rev. 1997, 97, 1515-1566
33. Ueno, T., Urano, Y., Setsukinai, K., Takakusa, H., Kojima, H., Kikuchi, K., Ohkubo, K., Fukuzumi, S., and Nagano, T. J. Am. Chem. Soc. 2004, 126, 14079-14085
34. Ueno, T., Urano, Y., Kojima, H., and Nagano, T. J. Am. Chem. Soc. 2006, 128, 10640-10641
35. Turro, N. J., Ramamurthy, V., and Scaiano, J. C. Modern Molecular Photochemistry of Organic Molecules; University Science Books: Sausalito, CA, 2010.
36. Kim, H., Burghart, A., Welch, M. B., Reibenspies, J., and Burgess, K. Chem. Commun. 1999, 1889-1890
37. Thoresen, L. H., Kim, H., Welch, M. B., Burghart, A., and Burgess, K. Synlett 1998, 1998, 1276-1278
38. Prieto, J. B., Arbeloa, F. L., Martínez, V. M., López, T. A., Amat-Guerri, F., Liras, M., and Arbeloa, I. L. Chem. Phys. Lett. 2004, 385, 29-35
39. Kollmannsberger, M., Gareis, T., Heinl, S., Daub, J., and Breu, J. Angew. Chem., Int. Ed. 1997, 36, 1333-1335
40. Amat-Guerri, F., Liras, M., Carrascoso, M. L., and Sastre, R. Photochem. Photobiol. 2003, 77, 577-584
41. Li, L., Nguyen, B., and Burgess, K. Bioorg. Med. Chem. Lett. 2008, 18, 3112-3116
42. Alberola, A., González Ortega, A., Luisa Sádaba, M., and Sañudo, C. Tetrahedron 1999, 55, 6555-6566
43. 2.
44. Prieto, J. B., Arbeloa, T., Liras, M., Martínez, V. M., and Arbeloa, F. L. J. Photochem. Photobiol. A: Chem. 2006, 184, 298-305
45. Cieslik-Boczula, K., Burgess, K., Li, L. L., Nguyen, B., Pandey, L., De Borggraeve, W. M., Van der Auweraer, M., and Boens, N. Photochem. Photobiol. Sci. 2009, 8, 1006-1015
46. Arbeloa, F. L., Prieto, J. B., Martínez, V. M., López, T. A., and Arbeloa, I. L. ChemPhysChem 2004, 5, 1762-1771
47. Meyer, S. D. and Schreiber, S. L. J. Org. Chem. 1994, 59, 7549-7552
48. Lai, R. Y., Fabrizio, E. F., Lu, L., Jenekhe, S. A., and Bard, A. J. J. Am. Chem. Soc. 2001, 123, 9112-9118
49. Lai, R. Y. and Bard, A. J. J. Phys. Chem. B 2003, 107, 5036-5042
50. Frisch, M. J. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
51. Koch, W. and Holthausen, M. C. A Chemist's Guide to Density Functional Theory, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2000.
52. Hall, H. K., Jr., Padias, A. B., Williams, P. A., Gosau, J.-M., Boone, H. W., and Park, D.-K. Macromolecules 1995, 28, 1-8