Kinetically controlled photoinduced electron transfer switching in Cu(I)-responsive fluorescent probes

Journal of the American Chemical Society

Volumn 132, Issue 2, 2010, Pages 737-747

  Chaudhry, Aneese F ^a   Verma, Manjusha ^a   Thomas Morgan, M ^a   Henary, Maged M ^a   Siegel, Nisan ^a   Hales, Joel M ^a   Perry, Joseph W ^a   Fahrni, Christoph J ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CU COMPLEXES; DRIVING FORCES; DYNAMIC EQUILIBRIA; ELECTRON TRANSFER; ELECTRONWITHDRAWING; FEMTOSECOND TIME-RESOLVED; FLUORESCENCE ENHANCEMENT; FLUORESCENCE SWITCHING; FLUORESCENT PROBES; PHOTO-INDUCED ELECTRON TRANSFER; PHOTOPHYSICAL; PHOTOPHYSICAL STUDIES; PUMP-PROBE EXPERIMENTS; QUANTUM CHEMICAL CALCULATIONS; RADIATIVE DEACTIVATION; REDUCTIVE ELECTRON TRANSFER; SOLUTION CHEMISTRY; SOLVENT MOLECULES; TERNARY COMPLEX; TETRADENTATE; TIME-RESOLVED FLUORESCENCE; TRIFLUOROACETIC ACIDS; VARIABLE TEMPERATURE;

COORDINATION REACTIONS; ELECTRON TRANSITIONS; EXPERIMENTS; FLUORESCENCE SPECTROSCOPY; METHANOL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOEXCITATION; PROBES; QUANTUM CHEMISTRY; QUENCHING;

FLUOROPHORES;

CUPROUS ION; FLUORESCENT DYE; METHANOL; TRIFLUOROACETIC ACID;

ABSORPTION SPECTROSCOPY; ARTICLE; CONTROLLED STUDY; ELECTRON TRANSPORT; FLUORESCENCE; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; QUANTUM CHEMISTRY;

COPPER; ELECTRONS; FLUORESCENT DYES; KINETICS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PHOTOCHEMISTRY; QUANTUM THEORY; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 74949141108     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja908326z     Document Type: Article

References (55)

1. Demchenko, A. P. Introduction to Fluorescence Sensing; Springer: New York, 2008.
2. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
3. Rurack, K. Spectrochim. Acta, Part A 2001, 57, 2161.
4. Nolan, E. M.; Lippard, S. J. Acc. Chem. Res. 2009, 42, 193.
5. Jiang, P. J.; Guo, Z. J. Coord. Chem. Rev. 2004, 248, 205.
6. Kikuchi, K.; Komatsu, K.; Nagano, T. Curr. Opin. Chem. Biol. 2004, 8, 182.
7. Cheng, T. Y.; Xu, Y. F.; Zhang, S. Y.; Zhu, W. P.; Qian, X. H.; Duan, L. P. J. Am. Chem. Soc. 2008, 130, 16160.
8. Xue, L.; Liu, C.; Jiang, H. Org. Lett. 2009, 11, 1655.
9. Prodi, L.; Bargossi, C.; Montalti, M.; Zaccheroni, N.; Su, N.; Bradshaw, J. S.; Izatt, R. M.; Savage, P. B. J. Am. Chem. Soc. 2000, 122, 6769.
10. Rurack, K.; Resch-Genger, U.; Bricks, J. L.; Spieles, M. Chem. Commun. 2000, 2103.
11. Nolan, E. M.; Lippard, S. J. J. Am. Chem. Soc. 2003, 125, 14270.
12. Yoon, S.; Albers, A. E.; Wong, A. P.; Chang, C. J. J. Am. Chem. Soc. 2005, 127, 16030.
13. Nolan, E. M.; Racine, M. E.; Lippard, S. J. Inorg. Chem. 2006, 45, 2742.
14. Meng, X. M.; Liu, L.; Hu, H. Y.; Zhu, M. Z.; Wang, M. X.; Shi, J.; Guo, Q. X. Tetrahedron Lett. 2006, 47, 7961.
15. Nolan, E. M.; Lippard, S. J. J. Am. Chem. Soc. 2007, 129, 5910.
16. Yoon, S.; Miller, E. W.; He, Q.; Do, P. H.; Chang, C. J. Angew. Chem., Int. Ed. 2007, 46, 6658.
17. Wang, J.; Qian, X. Org. Lett. 2006, 8, 3721.
18. For a comprehensive Review see also: Nolan, E. M.; Lippard, S. J. Chem. Rev. 2008, 108, 3443.
19. Rurack, K.; Kollmannsberger, M.; Resch-Genger, U.; Daub, J. J. Am. Chem. Soc. 2000, 122, 968.
20. (a) Yang, L.; McRae, R.; Henary, M. M.; Patel, R.; Lai, B.; Vogt, S.; Fahrni, C. J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 11179.
21. (b) Verma, M.; Chaudry, A. F.; Morgan, M. T.; Fahrni, C. J. Org. Biomol. Chem. 2010, 8, 363.
22. Cody, J.; Fahrni, C. J. Tetrahedron 2004, 60, 11099.
23. Zeng, L.; Miller, E. W.; Pralle, A.; Isacoff, E. Y.; Chang, C. J. J. Am. Chem. Soc. 2006, 128, 10.
24. Fakih, S.; Podinovskaia, M.; Kong, X.; Collins, H. L.; Schaible, U. E.; Hider, R. C. J. Med. Chem. 2008, 51, 4539.
25. Bricks, J. L.; Kovalchuk, A.; Trieflinger, C.; Nofz, M.; Büschel, M.; Tolmachev, A. I.; Daub, J.; Rurack, K. J. Am. Chem. Soc. 2005, 127, 13522.
26. Rurack, K.; Resch-Genger, U. Chem. Soc. Rev. 2002, 31, 116.
27. Verma, M.; Chaudhry, A. F.; Fahrni, C. J. Org. Biomol. Chem. 2009, 7, 1536.
28. Cody, J.; Mandal, S.; Yang, L.; Fahrni, C. J. J. Am. Chem. Soc. 2008, 130, 13023.
29. Fahrni, C. J.; Yang, L. C.; VanDerveer, D. G. J. Am. Chem. Soc. 2003, 125, 3799.
30. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259.
31. Addison, A. W. Inorg. Chim. Acta 1989, 162, 217.
32. Rived, F.; Rosés, M.; Bosch, E. Anal. Chim. Acta 1998, 374, 309.
33. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991.
34. Enderlein, J.; Erdmann, R. Opt. Commun. 1997, 134, 371.
35. Gritzner, G.; Kuta, J. Pure Appl. Chem. 1982, 54, 1527.
36. Shao, Y. E. A.; et al. Phys. Chem. Chem. Phys. 2006, 8, 3172.
37. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
38. (a) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
39. Balakrishnan, K. P.; Riesen, A.; Zuberbühler, A. D.; Kaden, T. A. Acta Crystallogr., Sect. C: Cryst. Soc. Commun. 1990, 46, 1236.
40. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
41. Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graphics 1996, 14, 33.
42. Kakos, S. H.; Dressel, L. T.; Bushendorf, J. D.; Kotarba, C. P.; Wijetunge, P.; Kulatilleke, C. P.; McGillivary, M. P.; Chaka, G.; Heeg, M. J.; Ochrymowycz, L. A.; Rorabacher, D. B. Inorg. Chem. 2006, 45, 923.
43. Shida, T. Electronic Absorption Spectra of Radical Ions; Elsevier: Amsterdam, 1988.
44. Kirchgessner, M.; Sreenath, K.; Gopidas, K. R. J. Org. Chem. 2006, 71, 9849.
45. Sumalekshmy, S.; Gopidas, K. R. Chem. Phys. Lett. 2005, 413, 294.
46. Milazzo, G.; Caroli, S. Tables of Standard Electrode Potentials; Wiley: New York, 1978.
47. Maroz, A.; Hermann, R.; Naumov, S.; Brede, O. J. Phys. Chem. A 2005, 109, 4690.
48. Blair, J. T.; Sahyun, M. R. V.; Sharma, D. K. J. Photochem. Photobiol., A 1994, 77, 133.
49. Yang, G.; Wu, H. J. Photochem. Photobiol., A 1992, 66, 69.
50. Güsten, H.; Heinrich, G.; Frühbeis, H. Ber. Bunsen Ges. Phys. Chem. 1977, 81, 810.
51. Yan, Z. L.; Wu, S. K. J. Lumin. 1993, 54, 303.
52. Rurack, K.; Bricks, J. L.; Schulz, B.; Maus, M.; Reck, G.; Resch-Genger, U. J. Phys. Chem. A 2000, 104, 6171.
53. McCrindle, R.; Ferguson, G.; McAlees, A. J.; Parvez, M.; Ruhl, B. L.; Stephenson, D. K.; Wieckowski, T. Dalton Trans. 1986, 2351.
54. Rorabacher, D. B. Chem. Rev. 2004, 104, 651.
55. Martin, M. J.; Endicott, J. F.; Ochrymowycz, L. A.; Rorabacher, D. B. Inorg. Chem. 1987, 26, 3012.