High-contrast Cu(I)-selective fluorescent probes based on synergistic electronic and conformational switching

Chemical Science

Volumn 2, Issue 6, 2011, Pages 1016-1024

  Chaudhry, Aneese F ^a   Mandal, Subrata ^a   Hardcastle, Kenneth I ^b   Fahrni, Christoph J ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONAL SWITCHES; CONFORMATIONAL SWITCHING; CRYSTAL STRUCTURE ANALYSIS; FLUORESCENCE ENHANCEMENT; FLUORESCENT PROBES; HIGH CONTRAST; LIGAND ARCHITECTURE; METAL BINDING; NON-RADIATIVE DEACTIVATION; PHOTO-INDUCED ELECTRON TRANSFER; PHOTOPHYSICAL; PYRAZOLINES; REDOX-ACTIVE; REDOX-ACTIVE METALS; SOLUTION STUDY; SWITCHING BEHAVIORS;

FLUORESCENCE; FLUOROPHORES; LIGANDS; PROBES; QUENCHING; TRANSITION METALS;

CRYSTAL STRUCTURE;

EID: 79957829381     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c1sc00024a     Document Type: Article

References (50)

1. J. Cody and C. J. Fahrni, Tetrahedron, 2004, 60, 11099.
2. R. F. H. Viguier and A. N. Hulme, J. Am. Chem. Soc., 2006, 128, 11370.
3. M. Taki, S. Iyoshi, A. Ojida, I. Hamachi and Y. Yamamoto, J. Am. Chem. Soc., 2010, 132, 5938.
4. L. C. Yang, R. McRae, M. M. Henary, R. Patel, B. Lai, S. Vogt and C. J. Fahrni, Proc. Natl. Acad. Sci. U. S. A., 2005, 102, 11179.
5. L. Zeng, E. W. Miller, A. Pralle, E. Y. Isacoff and C. J. Chang, J. Am. Chem. Soc., 2006, 128, 10.
6. M. Verma, A. F. Chaudhry, M. T. Morgan and C. J. Fahrni, Org. Biomol. Chem., 2010, 8, 363.
7. J. L. Bricks, A. Kovalchuk, C. Trieflinger, M. Nofz, M. Büschel, A. I. Tolmachev, J. Daub and K. Rurack, J. Am. Chem. Soc., 2005, 127, 13522.
8. M. Zhang, Y. Gao, M. Li, M. Yu, F. Li, L. Li, M. Zhu, J. Zhang, T. Yi and C. Huang, Tetrahedron Lett., 2007, 48, 3709.
9. W. Y. Lin, L. L. Long, L. Yuan, Z. M. Cao and J. B. Feng, Anal. Chim. Acta, 2009, 634, 262.
10. A. J. Weerasinghe, C. Schmiesing, S. Varaganti, G. Ramakrishna and E. Sinn, J. Phys. Chem. B, 2010, 114, 9413.
11. K. Rurack, M. Kollmannsberger, U. Resch-Genger and J. Daub, J. Am. Chem. Soc., 2000, 122, 968.
12. K. Rurack and U. Resch-Genger, Chem. Soc. Rev., 2002, 31, 116.
13. D. B. Rorabacher, Chem. Rev., 2004, 104, 651.
14. A. F. Chaudhry, M. Verma, M. T. Morgan, M.M. Henary, N. Siegel, J. M. Hales, J. W. Perry and C. J. Fahrni, J. Am. Chem. Soc., 2010, 132, 737.
15. A. P. De Silva, S. A. De Silva, A. S. Dissanayake and K. R. A. S. Sandanayake, Chem. Commun., 1989, 1054.
16. A. P. De Silva and H. Q. Nimal Gunaratne, Chem. Commun., 1990, 186.
17. A. P. De Silva, H. Q. N. Gunaratne and G. E. M. Maguire, Chem. Commun., 1994, 1213.
18. A. P. De Silva, H. Q. N. Gunaratne, T. Gunnlaugsson and M. Nieuwenhuizen, Chem. Commun., 1996, 1967.
19. K. Rurack, J. L. Bricks, B. Schulz, M. Maus, G. Reck and U. Resch-Genger, J. Phys. Chem. A, 2000, 104, 6171.
20. K. Rurack, U. Resch-Genger, J. L. Bricks and M. Spieles, Chem. Commun., 2000, 2103.
21. C. J. Fahrni, L. C. Yang and D. G. VanDerveer, J. Am. Chem. Soc., 2003, 125, 3799.
22. A. W. Addison, Inorg. Chim. Acta, 1989, 162, 217.
23. J. Cody, S. Mandal, L. C. Yang and C. J. Fahrni, J. Am. Chem. Soc., 2008, 130, 13023.
24. M. Verma, A. F. Chaudhry and C. J. Fahrni, Org. Biomol. Chem., 2009, 7, 1536.
25. M. A. Clark, K. Duffy, J. Tilbrewala and S. J. Lippard, Org. Lett., 2003, 5, 2051.
26. J. N. Demas and G. A. Crosby, J. Phys. Chem., 1971, 75, 991.
27. D. Rehm and A. Weller, Isr. J. Chem., 1970, 8, 259.
28. D. A. Deranleau, J. Am. Chem. Soc., 1969, 91, 4044.
29. M. M. Bernardo, R. R. Schroeder and D. B. Rorabacher, Inorg. Chem., 1991, 30, 1241.
30. M. R. Malachowski, M. Adams, N. Elia, A. L. Rheingold and R. S. Kelly, J. Chem. Soc., Dalton Trans., 1999, 2177.
31. K. K. Nanda, A. W. Addison, R. J. Butcher, M. R. McDevitt, T. N. Rao and E. Sinn, Inorg. Chem., 1997, 36, 134.
32. M. J. Schilstra, P. J. Birker, G. C. Verschoor and J. Reedijk, Inorg. Chem., 1982, 21, 2637.
33. G. Binsch, J. B. Lambert, B. W. Roberts and J. D. Roberts, J. Am. Chem. Soc., 1964, 86, 5564.
34. A. Bax, R. H. Griffey and B. L. Hawkins, J. Magn. Reson., 1983, 55, 301.
35. E. Shchori, J. Jagur-Grodzinski, Z. Luz and M. Shporer, J. Am. Chem. Soc., 1971, 93, 7133.
36. J. L. Dye, C. W. Andrews and J. M. Ceraso, J. Phys. Chem., 1975, 79, 3076.
37. E. Schmidt and A. I. Popov, J. Am. Chem. Soc., 1983, 105, 1873.
38. A. Delville, H. D. H. Stoever and C. Detellier, J. Am. Chem. Soc., 1985, 107, 4172.
39. P. H. M. Budzelaar, gNMR Version 5.0, Adept Scientific PLC, Letchworth, UK, 2002. This software calculates the full bandshape of signals that are broadened as a result of chemical exchange.
40. M. Pons and O. Millet, Prog. Nucl. Magn. Reson. Spectrosc., 2001, 38, 267.
41. P. Maslak and W. H. Chapman, J. Org. Chem., 1996, 61.
42. G. W. Dombrowski, J. P. Dinnocenzo, P. A. Zielinski, S. Farid, Z. M. Wosinska and I. R. Gould, J. Org. Chem., 2005, 70, 3791.
43. G. L. Closs and J. R. Miller, Science, 1988, 240, 440.
44. R. A. Marcus and N. Sutin, Biochim. Biophys. Acta, 1985, 811, 265.
45. J. Enderlein and R. Erdmann, Opt. Commun., 1997, 134, 371.
46. G. Gritzner and J. Kuta, Pure Appl. Chem., 1984, 56, 461.
47. APEX II, Bruker AXS, Inc., Madison, WI, 2005.
48. SAINT v. 6.45A, Bruker AXS, Inc., Madison, WI, 2003.
49. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112.
50. A. Platon, Multipurpose Crystallographic Tool, A. L. Spek, Utrecht University, Utrecht, The Netherlands, 2010.