The effect of phenyl substitution on the fluorescence characteristics of fluorescein derivatives via intramolecular photoinduced electron transfer

Photochemical and Photobiological Sciences

Volumn 9, Issue 9, 2010, Pages 1261-1268

  Zhang, Xian Fu ^a  

^a HEBEI NORMAL UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77956047217     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c0pp00184h     Document Type: Article

References (82)

1. W. C. Yang M. J. Schmerr R. Jackman W. Bodemer E. S. Yeung Capillary electrophoresis-based noncompetitive immunoassay for the prion protein using fluorescein-labeled protein a as a fluorescent probe Anal. Chem. 2005 77 4489 4494
2. S. Salleres F. Lo pez Arbeloa V. Marti nez T. Arbeloa I. Lopez Arbeloa Photophysics of Rhodamine 6G Laser Dye in Ordered Surfactant (C12TMA)/Clay (Laponite) Hybrid Films J. Phys. Chem. C 2009 113 965 970
3. K. Ergaieg R. Seux A comparative study of the photoinactivation of bacteria by meso-substituted cationic porphyrin, rose Bengal and methylene blue Desalination 2009 248 32 41
4. R. W. Dapson R. W. Horobin Dyes from a twenty-first century perspective Biotech. Histochem. 2009 84 135 137
5. L. H. C. Chua A. P. Robertson W. K. Yee E. B. Shuy E. Y. M. Lo T. T. Lim S. K. Tan Use of Fluorescein as a Ground Water Tracer in Brackish Water Aquifers Ground Water 2007 45 85 88
6. I. Rosenthal P. Peretz K. A. Muszkat Thermochromic and hyperchromic effects in Rhodamine B solutions J. Phys. Chem. 1979 83 350 353
7. D. F. Eaton Reference materials for fluorescence measurement Pure Appl. Chem. 1988 60 1107 1114
8. Y. Duan M. Liu W. Sun M. Wang S. Liu Q. X. Li Recent Progress on Synthesis of Fluorescein Probes Mini-Rev. Org. Chem. 2009 6 35 43
9. N. Boens W. Qin N. Basari A. Orte E. M. Talavera J. M. Alvarez-Pez Photophysics of the Fluorescent pH Indicator BCECF J. Phys. Chem. A 2006 110 9334 9343
10. P. G. Bowers G. Porter Triplet state quantum yields for some aromatic hydrocarbons and xanthene dyes in dilute solution Proc. R. Soc. 1967 A299 348 352
11. J. H. Brannon D. Magde Absolute Quantum Yield Determination by Thermal Blooming. Fluorescein J. Phys. Chem. 1978 82 705
12. X. Zhang Q. Liu A. Son Q. Zhang F. Zhang F. Zhao Photophysical properties of dibenzofluorescein and the presence of its tautomers or prototropic forms in organic solvents Photochem. Photobiol. Sci. 2008 7 299 302
13. N. I. Rtishchev D. V. Samoilov V. P. Martynova A. V. El'tsov Luminescence Properties of Nitro Derivatives of Fluorescein Russ. J. Gen. Chem. 2001 71 1467 1478
14. R. Duchowicz M. L. Ferrer A. U. Acun Kinetic Spectroscopy of Erythrosin Phosphorescence and Delayed Fluorescence in Aqueous Solution at Room Temperature Photochem. Photobiol. 1998 68 494 501
15. A. I. Ponyaev V. P. Martynova A. V. El'tsov Photophysical and Photocatalytic Parameters of Sulfo and Tetrabromosulfo Derivatives of Fluorescein Russ. J. Gen. Chem. 2001 71 1744 1750
16. L. Crovetto J. M. Paredes R. Rios E. M. Talavera J. M. Alvarez-Pez Photophysics of a xanthenic derivative dye useful as an "on/off" fluorescence probe J. Phys. Chem. A 2007 111 13311 13320
17. G. R. Fleming A. W. E. Knight J. M. Morris R. J. S. Morrison G. W. Robinson Picosecond Fluorescence Studies of Xanthene Dyes J. Am. Chem. Soc. 1977 99 4306 4311
18. L. S. Forster D. Dudley The Luminescence of Fluorescein Dyes J. Phys. Chem. 1962 66 838 840
19. E. Gandin Y. Lion A. v. d. Horst Quantum Yield of Singlet Oxygen Production by Xanthene Derivatives Photochem. Photobiol. 1983 37 271 278
20. H. Gratz A. Penzkofer Triplet-triplet absorption of some organic molecules determined by picosecond laser excitation and time-delayed picosecond light continuum probing J. Photochem. Photobiol., A 1999 127 21 30
21. E. Klimtchuk M. A. J. Rodgers D. C. Neckers Laser Flash Photolysis Studies of Novel Xanthene Dye Derivatives J. Phys. Chem. 1992 96 9817 9820
22. L. Lindqvist The Triplet State of Fluoresceix in Sulfcric Acid J. Phys. Chem. 1963 67 1701
23. J. M. Larkin W. R. Donaldson T. H. Foster R. S. Knox Reverse intersystem crossing from a triplet state of rose bengal populated by sequential 532-+ 1064-nm laser excitation Chem. Phys. 1999 244 319 330
24. D. Magde R. Wong P. G. Seybold Fluorescence Quantum Yields and Their Relation to Lifetimes of Rhodamine 6G and Fluorescein in Nine Solvents: Improved Absolute Standards for Quantum Yields Photochem. Photobiol. 2002 75 327 334
25. J. Paczkowski J. J. M. Lamberts B. Paczkowska D. C. Neckers Photophysical properties of rose bengal and its derivatives (XII) J. Free Radicals Biol. Med. 1985 1 341 351
26. A. Penzkofer A. Beidoun M. Daiber Intersystem-crossing and excited-state absorption in eosin Y solutions determined by picosecond double pulse transient absorption measurements J. Lumin. 1992 51 297 314
27. S. Reindl A. Penzkofer Triplet quantum yield determination by picosecond laser double-pulse fluorescence excitation Chem. Phys. 1996 213 429 438
28. S. Reindl A. Penzkofer Higher excited-state triplet-singlet intersystem crossing of some organic dyes Chem. Phys. 1996 211 431 439
29. B. Soep A. Kellman M. Martin L. Lindqvist Study of triplet quantum yields using a tunable dye laser Chem. Phys. Lett. 1972 13 241 244
30. R. Sjoback J. Nygren M. Kubista Absorption Fluorescence Properties of Fluorescein Spectrochim. Acta, Part A 1995 51 L7 L21
31. W. R. Orndorff R. C. Gibbs C. V. Shapiro The Absorption Spectra of Fluorescein, Fluoran and Some Related Compounds J. Am. Chem. Soc. 1928 50 819 828
32. K. K. Rohatgi G. S. Singhal Determination of Average Molar Absorptivity for Self-Absorption of Fluorescent Radiation in Fluorescein Solution Anal. Chem. 1962 34 1702 1706
33. H. E. Lessing and A. v. Jena, in Laser Handbook, ed., M. L. Stitch, North-Holland, Amsterdam, 1979, pp. 753
34. L. Lindqvist A flash photolysis study of fluorescein Arkiv Kemi 1960 16 79 83
35. V. Kasche L. Lindqvist Transient Species in the Photochemistry of Eosin Photochem. Photobiol. 1965 4 923 933
36. V. Wintgens J. C. Scaiano S. M. Linden D. C. Neckers Transient Phenomena in the Laser Flash Photolysis of Rose Bengal C-2′Ethyl Ester C-6 Sodium Salt J. Org. Chem. 1989 54 5242 5246
37. R. Brennetot J. Georges Transient absorption of the probe beam by the erythrosine triplet in pulsed-laser thermal lens spectrometry: the influence of the solvent, oxygen and dye concentration Chem. Phys. Lett. 1998 289 19 24
38. D. Magde G. E. Rojas P. G. Seybold Solvent Dependence of the Fluorescence Lifetimes of Xanthene Dyes Photochem. Photobiol. 1999 70 737 744
39. D. C. Neckers S. N. Gupta Spectral Properties of Rose Bengal Derivatives in Polar and Nonpolar Solvents J. Org. Chem. 1987 52 936 938
40. N. Klonis, A. H. A. Clayton, E. W. Voss, and W. H. Sawyer, Spectral properties of fluorescein in solvent-water mixtures: applications as a probe of hydrogen bonding environments in biological systems, Photochem. Photobiol., 1998, 67, 500-510
41. H. G. Brittain F. S. Richardson Solvent Induced Circularly Polarized Emission from Fluorescein J. Phys. Chem. 1976 80 2590 2592
42. S. D.-M. Islam O. Ito Solvent effects on rates of photochemical reactions of rose bengal triplet state studied by nanosecond laser photolysis J. Photochem. Photobiol., A 1999 123 53 59
43. N. Klonis W. H. Sawyer Effect of Solvent-Water Mixtures on the Prototropic Equilibria of Fluorescein and on the Spectral Properties of the Monoanion Photochem. Photobiol. 2000 72 179 185
44. K. G. Casey E. L. Quitevis Effect of Solvent Polarity on Nonradiative Processes in Xanthene Dyes: Rhodamine B in Normal Alcohols J. Phys. Chem. 1988 92 6590 6594
45. M. Martin L. Lindqvist The pH dependence of fluorescein fluorescence J. Lumin. 1975 10 381 390
46. R. Dunsbach R. Schmidt Deactivation of excited xanthene dye dimers J. Photochem. Photobiol., A 1995 85 275 279
47. M. Arik N. Celebi Y. Onganer Fluorescence quenching of fluorescein with molecular oxygen in solution J. Photochem. Photobiol., A 2005 170 105 111
48. W. J. Svirbely N. E. Sharpless The Quenching of the Fluorescence of the Eosin Ion J. Am. Chem. Soc. 1954 76 1404 1409
49. L. Flamigni Inclusion of Fluorescein and Halogenated Derivatives in alpha-, beta-, and gama-Cyclodextrins. A Steady-State and Picosecond Time-Resolved Study J. Phys. Chem. 1993 97 9566 9572
50. S. Biswas S. C. Bhattacharya P. K. Sen S. P. Moulik Absorption and emission spectroscopic studies of fluorescein dye in alkanol, micellar and microemulsion media J. Photochem. Photobiol., A 1999 123 121 128
51. P. Bilski R. Dabestani C. F. Chignell Influence of Cationic Surfactant on the Photoprocesses of Eosine and Rose Bengal in Aqueous Solutlon J. Phys. Chem. 1991 95 5784 5791
52. A. Song J. Zhang M. Zhang T. Shen J. a. Tang Spectral properties and structure of fluorescein and its alkyl derivatives in micelles Colloids Surf., A 2000 167 253 262
53. B. B. Bhowmik P. Ganguly Photophysics of xanthene dyes in surfactant solution Spectrochim. Acta, Part A 2005 61 1997 2003
54. P. V. Kamat M. A. Fox Photophysics and Photochemistry of Xanthene Dyes in Polymer Solutions and Films J. Phys. Chem. 1984 88 2297 2302
55. S. N. Gupta S. M. Linden A. Wrzyszczynski D. C. Neckers Light-Induced Spectral Changes in Rose Bengal End-Capped Polystyrene Macromolecules 1988 21 51 55
56. A. V. Deshpande E. B. Namdas Spectroscopic properties of Na-fluorescein in polyacrylic acid films J. Photochem. Photobiol., A 1997 110 177 182
57. M. E. Daraio E. S. RomaÂn Aggregation and Photophysics of Rose Bengal in Alumina-Coated Colloidal Suspensions Helv. Chim. Acta 2001 84 2601 2614
58. H. Zhang Y. Zhou M. Zhang T. Shen Y. Li D. Zhu Photoinduced interaction between fluorescein ester derivatives and CdS colloid J. Colloid Interface Sci. 2003 264 290 295
59. P. Siejak D. Fraückowiak Spectral Properties of Fluorescein Molecules in Water with the Addition of a Colloidal Suspension of Silver J. Phys. Chem. B 2005
60. A. Imhof M. Megens J. J. Engelberts D. T. N. d. Lang R. Sprik W. L. Vos Spectroscopy of Fluorescein (FITC) Dyed Colloidal Silica Spheres J. Phys. Chem. B 1999 103 1408 1415
61. S. K. Lam E. Namdas D. Lo Effects of oxygen and temperature on phosphorescence and delayed fuorescence of erythrosin B trapped in sol-gel silica J. Photochem. Photobiol., A 1998 118 25 30
62. T. Fujii A. Ishii Y. Kurihara M. Anpo Multiple fluorescence spectra of fluorescein molecules encapsulated in the silica xerogel prepared by the sol-gel reaction Res. Chem. Intermed. 1993 19 333 342
63. T. Fujii A. Ishii N. Takusagawa M. Anpo Fluorescence spectra and chemical species of fluorescein molecules adsorbed on a calcinated porous Vycor glass Res. Chem. Intermed. 1992 17 1 14
64. A. K. Dutta C. Salesse A Spectroscopic and Epifluorescence Microscopic Study of (Hexadecanoylamino)fluorescein Aggregates at the Air-Water Interface and in Langmuir-Blodgett Films Langmuir 1997 13 5401 5408
65. 2 Zeit. Physik. Chem. 2007 221 941 948
66. M. A. Ryan E. C. Fitzgerald M. T. Spitler Internal Reflection Flash Photolysis Study of the Photochemistry of Eosin at TiO2 Semiconductor Electrodes J. Phys. Chem. 1989 93 6150 6156
67. N. A. Domnina A. M. Saletskii Polarized Luminescence of Erythrosine Molecules Adsorbed on a Semiconductor-Dielectric Structure Opt. Spectrosc. 2003 95 42 45
68. R. Antoine A. A. Tamburello-Luca P. Hebert P. F. Brevet H. H. Girault Picosecond dynamics of EosinB at the air/water interface by time-resolved second harmonic generation: orientational randomization and rotational relaxation Chem. Phys. Lett. 1998 288 138 146
69. J. R. Unruh G. Gokulrangan G. S. Wilson C. K. Johnson Fluorescence Properties of Fluorescein, Tetramethylrhodamine and Texas Red Linked to a DNA Aptamer Photochem. Photobiol. 2005 81 682 690
70. J. R. Falck M. Krieger J. L. Goldstein M. S. Brown Preparation and Spectral Properties of Lipophilic Fluorescein Derivatives: Application to Plasma Low-Density Lipoprotein J. Am. Chem. Soc. 1981 103 7396 7398
71. L. C. Abbott P. MacFaul L. Jansen J. Oakes J. R. Lindsay Smith J. N. Moore Spectroscopic and photochemical studies of xanthene and azo dyes on surfaces: cellophane as a mimic of paper and cotton Dyes Pigm. 2001 48 49 56
72. A. Orte L. Crovetto E. M. Talavera N. Boens J. M. Alvarez-Pez Absorption and emission study of 2′,7′-difluorofluorescein and its excited-state buffer-mediated proton exchange reactions J. Phys. Chem. A 2005 109 734 737
73. L. Crovetto A. Orte E. M. Talavera J. M. Alvarez-Pez Global Compartmental Analysis of the Excited-State Reaction between Fluorescein and ((+-)-N-Acetyl Aspartic Acid J. Phys. Chem. B 2004 108 6082 6092
74. A. I. Ponyaev V. P. Martynova A. V. El'tsov Photophysical and Photocatalytic Parameters of Sulfo and Tetrabromosulfo Derivatives of Fluorescein Russ. J. Gen. Chem. 2001 71 1744 1750
75. X. F. Zhang Q. Liu H. Wang Z. Fu F. Zhang Photophysical behavior of lipophilic xanthene dyes without the involvement of photoinduced electron transfer mechanism J. Photochem. Photobiol., A 2008 200 307 313
76. X.-F. Zhang I. Zhang L. Liu Photophysics of Halogenated Fluoresceins: Involvement of Both Intramolecular Electron Transfer and Heavy Atom Effect in the Deactivation of Excited States Photochem. Photobiol. 2010 86 492 498
77. H. Diehl N. Horchak-Morris Studies on fluorescein-V The absorbance of fluorescein in the ultraviolet, as a function of pH Talanta 1987 34 739 741
78. H. Diehl Studies on fluorescein-VI Absorbance of the various prototropic forms of yellow fluorescein in aqueous solution Talanta 1989 36 413 415
79. B. Valeur, in Molecular Fluorescence: Principles and Applications, ed., B. Valeur, Wiley-VCH Verlag GmbH, Weinheim, 2001, pp. 56-59
80. P. Wardman E. D. Clarke Oxygen inhibition of nitroreductase: electron transfer from nitro radical-anions to oxygen Biochem. Biophys. Res. Commun. 1976 69 942 949
81. H.-Y. Pan F.-Y. Ge L.-G. Chen Synthesis, Separation and Characterization of Aminofluorescein Chin. J. App. Chem. 2006 23 193 197
82. R. Markuszewski H. Diehl Structure of red and orange fluorescein Talanta 1980 27 937 943