Diphenylhexatrienes as photoprotective agents for ultrasensitive fluorescence detection

Journal of Physical Chemistry A

Volumn 114, Issue 12, 2010, Pages 4099-4108

  Pfiffi, Daniela ^a   Bier, Brigitte A ^a   Marian, Christel M ^a   Schaper, Klaus ^a   Seidel, Claus A M ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENEFICIAL EFFECTS; COULOMBIC EFFECTS; DIFFUSION CONTROLLED; ELECTRON TRANSFER; ELECTRON-DEFICIENT; ELECTRON-DONATING; EMISSION ENERGIES; EXCITED TRIPLET STATE; FLUORESCENCE CORRELATION SPECTROSCOPY; FLUORESCENCE FLUCTUATION SPECTROSCOPY; FLUORESCENCE SIGNALS; LASER DYES; LASER SCANNING MICROSCOPY; OPTICAL SPECTROSCOPY; PARENT COMPOUNDS; PHOTO-STABILITY; QUANTUM CHEMICAL CALCULATIONS; QUENCHING CONSTANT; RHODAMINE 123; SINGLE-MOLECULE; SINGLET STATE; TRIPLET ENERGY TRANSFER; TRIPLET QUENCHING; TRIPLET STATE; ULTRASENSITIVE FLUORESCENCE;

CHEMICAL BONDS; CYCLIC VOLTAMMETRY; DIGITAL LIBRARIES; ELECTRONEGATIVITY; ELECTRONIC PROPERTIES; ENERGY TRANSFER; ETHANOL; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; FREE RADICAL REACTIONS; FREE RADICALS; OPTICAL PROPERTIES; QUANTUM CHEMISTRY; RHODIUM; SPECTROSCOPIC ANALYSIS;

QUENCHING;

EID: 77950263356     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp909033x     Document Type: Article

References (81)

1. Yamashita, M.; Kuniyasu, A.; Kashiwagi, H. J. Chem. Phys. 1977, 66, 986.
2. Drexhage, K. H.; Schäfer, F. P. Structure and properties of laser dyes. In Topics in Applied Physics; Springer Verlag: Berlin, 1973; Vol.1, pp 144.
3. Gonçalves, M. S. T. Chem. Rev. 2009, 109, 190.
4. Pawley, J. B. Handbook of Biological Confocal Microscopy, 3rd ed.; Springer: New York, 2006.
5. Hell, S. W. Science 2007, 316, 1153.
6. Widengren, J.; Kudryavtsev, V.; Antonik, M.; Berger, S.; Gerken, M.; Seidel, C. A. M. Anal. Chem. 2006, 78, 2039.
7. Haustein, E.; Schwille, P. Annu. Rev. Biophys. Biomol. Struct. 2007, 36, 151.
8. Widengren, J.; Chmyrov, A.; Eggeling, C.; Löfdahl, P. A.; Seidel, C. A. M. J. Phys. Chem. A 2007, 111, 429.
9. Vogelsang, J.; Cordes, T.; Forthmann, C.; Steinhauer, C.; Tinnefeid, P. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 8107.
10. Hofkens, J.; Cotlet, M.; Vosch, T.; Tinnefeid, P.; Weston, K. D.; Ego, C.; Grimsdale, A.; Müllen, K.; Beljonne, D.; Bredas, J. L.; Jordens, S.; Schweitzer, G.; Sauer, M.; De Schryver, F. Proc. Natl. Acad Sci. U.S.A. 2003, 100, 13146.
11. Liphardt, B.; Lüttke, W. Opt. Commun. 1983, 48, 129.
12. Sauer, M.; Han, K. T.; Müller, R.; Schulz, A.; Tadday, R.; Seeger, S.; Wolfrum, J.; Arden-Jacob, J.; Deltau, G.; Marx, N. J.; Drexhage, K. H. J. Fluoresc. 1993, 3, 131.
13. Ernsting, N. P.; Kaschke, M.; Kleinschmidt, J.; Drexhage, K. H.; Huth, V. Chem. Phys. 1988, 122, 431.
14. Eggeling, C.; Widengren, J.; Rigler, R.; Seidel, C. A. M. Photostabilities of fluorescent dyes for single-molecule spectroscopy: Mechanisms and experimental methods for estimating photobleaching in aqueous solution. In Applied Fluorescence in Chemistry, Biology and Medicine; Springer: Berlin, 1999; pp 193.
15. Eggeling, C.; Widengren, J.; Rigler, R.; Seidel, C. A. M. Anal. Chem. 1998, 70, 2651.
16. Widengren, J.; Rigler, R. Bioimaging 1996, 4, 149.
17. Vogelsang, J.; Kasper, R.; Steinhauer, C.; Person, B.; Heilemann, M.; Sauer, M.; Tinnefeid, P. Angew. Chem., Int. Ed. 2008, 47, 5465.
18. Rasnik, I.; McKinney, S. A.; Ha, T. Nat. Methods 2006, 3, 891.
19. Ferguson, M. W.; Beaumont, P. C.; Jones, S. E.; Navaratnam, S.; Parsons, B. J. Phys. Chem. Chem. Phys. 1999, 1, 261.
20. Ringemann, C.; Schönle, A.; Giske, A.; von Middendorff, C.; Hell, S. W.; Eggeling, C. ChemPhysChem 2008, 9, 612.
21. Förster, T. Discusssions Faraday Soc. 1959, 7.
22. Förster, T. Ann. Phys. 1948, 2, 55.
23. Förster, T. Fluoreszenz Organischer Verbindungen; Vandenhoeck and Ruprecht: Göttingen, Germany, 1951.
24. Dexter, D. L. J. Chem. Phys. 1953, 21, 836.
25. Rehm, D.; Weller, A. Israel J.Chem. 1970, 8, 259.
26. Rehm, D.; Weller, A. Z. Phys. Chem. 1970, 69, 183.
27. Marcus, R. A. J. Chem. Phys. 1956, 24, 966.
28. Kavarnos, G. J.; Turro, N. J. Chem. Rev. 1986, 86, 401.
29. In order to describe the transitions involved in these processes we followed IUPAC conventions and denoted the excited state first and the ground state last. Thus absorption is marked by "←" and an emission is marked by "→".
30. Mills, I.; Cvitas, T.; Homann, K.; Kallay, K.; Kuchitsu, K. Quantities, Units and Symbols in Physical Chemistry, 2nd ed. ; Blackwell Science: Oxford, U.K., 1993.
31. Wardman, P. J. Phys. Chem. Ref. Data 1989, 18, 1637.
32. Polívka, T.; Sundström, V. Chem. Rev. 2004, 104, 2021.
33. Furuichi, K.; Sashima, T.; Koyama, Y. Chem. Phys. Lett. 2002, 356, 547.
34. Hilinski, E. F.; McGowan, W. M.; Sears, D. F.; Saltiel, J. J. Phys. Chem. 1996, 100, 3308.
35. Ye, J. F.; Chen, H.; Note, R.; Mizuseki, H.; Kawazoe, Y. Int. J. Quantum Chem. 2007, 107, 2006.
36. For the calculations regarding RH123, the ethyl ester was used instead of the methyl ester.
37. Sonoda, Y.; Kawanishi, Y.; Ikeda, T.; Goto, M.; Hayashi, S.; Yoshida, Y.; Tanigaki, N.; Yaso, K. J. Phys. Chem. B 2003, 107, 3376.
38. Zhuang, Z. P.; Kung, M. P.; Kung, H. F. J. Med. Chem. 2006, 49, 2841.
39. Trepanier, V. E.; Fillion, E. Organometallics 2007, 26, 30.
40. Kauffman, J. M.; Moyna, G. J. Org. Chem. 2003, 68, 839.
41. Alford, P. C.; Palmer, T. F. Chem. Phys. Lett. 1982, 86, 248.
42. Alford, P. C.; Palmer, T. F. Chem. Phys. Lett. 1986, 127, 19.
43. Sonoda, Y.; Kwok, W. M.; Petrasek, Z.; Ostler, R.; Matousek, P.; Towrie, M.; Parker, A. W.; Phillips, D. J. Chem. Soc. Perkin Trans. 2 2001, 308.
44. Sonoda, Y.; Modi, H.; Sakuragi, M.; Suzuki, Y. Chem. Lett. 1998, 349.
45. Barluenga, J.; Model, P.; Aznar, F.; Valdes, C. Adv. Synth. Catal. 2006, 348, 347.
46. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829.
47. Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133.
48. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
49. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
50. Furche, F.; Ahlrichs, R. J. Chem. Phys. 2002, 117, 7433.
51. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kolmel, C. Chem. Phys. Lett. 1989, 162, 165.
52. Schade, B.; Hagen, V.; Schmidt, R.; Herbrich, R.; Krause, E.; Eckardt, T.; Bendig, J. J. Org. Chem. 1999, 64, 9109.
53. Klamt, A.; Schüürmann, G. J. Chem. Soc, Perkin Trans. 2 1993, 799.
54. Grimme, S.; Waletzke, M. J. Chem. Phys. 1999, 111, 5645.
55. Marian, C. M.; Gilka, N. J. Chem. Theory Comput. 2008, 4, 1501.
56. Kleinschmidt, M.; Marian, C. M.; Waletzke, M.; Grimme, S. J. Chem. Phys. 2009, 130, 044708.
57. Magde, D.; Elson, E. L.; Webb, W. W. Biopolymers 1974, 13, 29.
58. Elson, E. L.; Magde, D. Biopolymers 1974, 13, 1.
59. Magde, D.; Elson, E. L.; Webb, W. W. Phys. Rev. Lett. 1972, 29, 705.
60. Widengren, J.; Mets, Ü.; Rigler, R. J. Phys. Chem. 1995, 99, 13368.
61. Enderlein, J.; Gregor, I.; Patra, D.; Dertinger, T.; Kaupp, U. B. ChemPhysChem 2005, 6, 2324.
62. Eggeling, C.; Volkmer, A.; Seidel, C. A. M. ChemPhysChem 2005, 6, 791.
63. Christensen, R. L.; Barney, E. A.; Broene, R. D.; Galinato, M. G. I.; Frank, H. A. Arch. Biochem. Biophys. 2004, 430, 30.
64. Dupuy, B.; Montagu, M. Analyst 1997, 122, 783.
65. Kohler, B. E.; Itoh, T. J. Phys. Chem. 1988, 92, 5120.
66. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry; Marcel Dekker Inc.: New York, 1993.
67. Saltiel, J.; Crowder, J. M.; Wang, S. J. J. Am. Chem. Soc. 1999, 121, 895.
68. Evans, D. F.; Tucker, J. N. J. Chem. Soc., Faraday Trans. 2 1972, 68, 174.
69. Heupel, M.; Gregor, I.; Becker, S.; Thiel, E. Int. J. Photoenergy 1999, 1, 165.
70. Menzel, R.; Bornemann, R.; Thiel, E. Phys. Chem. Chem. Phys. 1999, 1, 2435.
71. Kunavin, N. I.; Nurmukhametov, R. N.; Khachaturova, G. T. Zh. Prikl. Spektrosk. 1977, 26, 1023.
72. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
73. Gregor, I.; Heupel, M.; Thiel, E. Chem. Phys. 2001, 272, 185.
74. Stracke, F.; Heupel, M.; Thiel, E. J. Photochem. Photobiol. A 1999, 126, 51.
75. Schweitzer, C.; Schmidt, R. Chem. Rev. 2003, 103, 1685.
76. Köpsel, C.; Moltgen, H.; Schuch, H.; Auweter, H.; Kleinermanns, K.; Martin, H. D.; Bettermann, H. J. Mol. Struct. 2005, 750, 109.
77. Balzani, V.; Bolletta, F.; Scandola, F. J. Am. Chem. Soc. 1980, 102, 2152.
78. Nau, W. M.; Scaiano, J. C. J. Phys. Chem. 1996, 100, 11360.
79. Wamser, C. C.; Medary, R. T.; Kochevar, I. E.; Turro, N. J.; Chang, P. L. J. Am. Chem. Soc. 1975, 97, 4864.
80. Cheng, G.; Peng, X.; Hao, G.; Kennedy, V. O.; Ivanov, I. N.; Knappenberger, K.; Hill, T. J.; Rodgers, M. A. J.; Kenney, M. E. J. Phys. Chem. A 2003, 107, 3503.
81. Albinsson, B.; Mårtensson, J. J. Photochem. Photobiol. C 2008, 9, 138.