Photophysics and photochemistry of hydrophilic cyanine dyes in normal and reverse micelles

Photochemical and Photobiological Sciences

Volumn 1, Issue 3, 2002, Pages 211-218

  Tatikolov, Alexander S ^a,b   Costa, Sílvia M B ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b EMANUEL INSTITUTE OF BIOCHEMICAL PHYSICS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

CYANINE DYE; CYCLOHEXANE; DITHIAZANINE; DOCUSATE SODIUM; HEXANOL; SURFACTANT; TRITON X 100; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONTROLLED STUDY; FLUORESCENCE; HYDROPHILICITY; ISOMERISM; MICELLE; MOLECULAR PHYSICS; PHOTOCHEMISTRY; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS;

EID: 0041408825     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b110450k     Document Type: Article

References (51)

1. N. Nakashima T. Kunitake Drastic fluorescence enhancement of cyanine dyes bound to synthetic bilayer membranes. Its high sensitivity to the chemical structure and the physical state of the membrane J. Am. Chem. Soc. 1982 104 4261-4262.
2. O. Valdes-Aguilera L. Cincotta J. Foley I. E. Kochevar Photobleaching of a cyanine dye in solution and in membranes Photochem. Photobiol. 1987 45 337-344.
3. F. García-Jiménez M. I. Khramov R. Sánchez-Obregón O. Collera Formation of J-aggregates of cyanine dyes in bilayer lipid vesicles Chem. Phys. Lett. 2000 331 42-46.
4. I. Timcheva V. Maximova T. Deligeorgiev N. Gadjev K. H. Drexhage I. Petkova Homodimeric monomethine cyanine dyes as fluorescent probes of biopolymers J. Photochem. Photobiol., B 2000 58 130-135.
5. R. Humphry-Baker M. Grätzel R. Steiger Drastic fluorescence enhancement and photochemical stabilization of cyanine dyes through micellar systems J. Am. Chem. Soc. 1980 102 847-848.
6. A. Datta D. Mandal S. K. Pal K. Bhattacharyya Photoisomerisation near a hydrophobic surface. Diethyloxadicarbocyanine iodide in a reverse micelle Chem. Phys. Lett. 1997 278 77-82.
7. S. K. Pal A. Datta D. Mandal K. Bhattacharyya Photoisomerization of diethyloxadicarbocyanine iodide in micelles Chem. Phys. Lett. 1998 288 793-798.
8. H. Sato M. Kawasaki K. Kasatani N. Nakashima K. Yoshihara Interaction of a cationic dye and anionic detergent above and below the critical micelle concentration as revealed by fluorescence characteristics Bull. Chem. Soc. Jpn. 1983 56 3588-3594.
9. A. K. Chibisov V. I. Prokhorenko H. Görner Effects of surfactants on the aggregation behaviour of thiacarbocyanine dyes Chem. Phys. 1999 250 47-60.
10. A. K. Chibisov G. V. Zakharova H. Görner Photoprocesses of thiamonomethinecyanine monomers and dimers Phys. Chem. Chem. Phys. 2001 3 44-49.
11. A. K. Mandal M.K. Pal Strong fluorescence emission by H-aggregates of the dye thiacyanine in the presence of the surfactant aerosol-OT Chem. Phys. 2000 253 115-124.
12. Z. Zhang C. Liu Photochemistry of a cyanine dye in reversed micelles J. Photochem. Photobiol., A 2000 130 139-143.
13. F. Grieser M. Lay P. J. Thistlethwaite Excited-state torsional relaxation in 1,1′-dihexyl-3,3,3′3′-tetramethylindocarbocyanine iodide: application to the probing of micelle structure J. Phys. Chem. 1985 89 2065-2070.
14. C. A. T. Laia, Squaraines and Cyanines in Liquid Interfaces: Dynamic Aspects in Microemulsions and Homogeneous Media, PhD Thesis, Instituto Superior Técnico, Lisbon, Portugal, 1999.
15. M. Caselli F. Momicchioli G. Ponterini Modelling of the cis–trans partitioning in the photoisomerizations of cyanines and stilbene derivatives Chem. Phys. Lett. 1993 316 41-46.
16. D. N. Dempster T. Morrow R. Rankin G. F. Thompson Photochemical characteristics of cyanine dyes. Part 1. 3,3′-diethyloxadicarbocyanine iodide and 3,3′-diethylthiadicarbocyanine iodide J. Chem. Soc., Faraday Trans. 2 1972 68 1479-1496.
17. A. K. Chibisov G. V. Zakharova H. Görner Yu. A. Sogulyaev I. L. Mushkalo A. I. Tolmachev Photorelaxation processes in covalently linked indocarbocyanine and thiacarbocyanine dyes J. Phys. Chem. 1995 99 886-893.
18. The Theory of the Photographic Process, 4th edn., ed. T. H. James, Macmillan, New York, 1977.
19. R. F. Khairutdinov N. Serpone Photophysics of cyanine dyes: subnanosecond relaxation dynamics in monomers, dimers, and H- and J-aggregates in solution J. Phys. Chem. B 1997 101 2602-2610.
20. A. H. Herz Dye-dye interaction of cyanines in solution and at AgBr surfaces Photogr. Sci. Eng. 1974 18 323-334.
21. E. E. Jelley Spectral absorption and fluorescence of dyes in the molecular state Nature 1936 138 1009-1010.
22. G. Scheibe Über die Veränderlichkeit des Absorptionsspektrums einiger Sensibilisierungsfarbstoffe und deren Ursache Angew. Chem. 1936 49 563.
23. P. Bilski R. N. Holt C. F. Chignell Premicellar aggregates of Rose Bengal with cationic and zwitterionic surfactants J. Photochem. Photobiol., A 1997 110 67-74.
24. M. Fischer J. Georges Use of thermal lens spectrometry for the investigation of dimerization equilibria of rhodamine 6G in water and aqueous micellar solutions Spectrochim. Acta, Part A 1997 53 1419-1430.
25. A. K. Chibisov G. V. Zakharova H. Görner Photoprocesses in dimers of thiacarbocyanines Phys. Chem. Chem. Phys. 1999 1 1455-1460.
26. V. I. Avdeeva B. I. Shapiro J-aggregation of thiamonomethinecyanines: 4. Aggregation in solutions J. Sci. Appl. Photogr. 1998 39 543-554.
27. V. I. Avdeeva B. I. Shapiro Formation of J-aggregates of thiamonomethinecyanine from dimers. Block construction of aggregates Zh. Nauchn. Prikl. Fotogr. 1999 44 20-27.
28. B. Neumann P. Pollmann Investigation of two cyanine dyes at normal and high pressure by UV/Vis spectroscopy Phys. Chem. Chem. Phys. 2000 2 4784-4792.
29. A. S. Tatikolov S. M. B. Costa Effects of normal and reverse micellar environment on the spectral properties, isomerization and aggregation of a hydrophilic cyanine dye Chem. Phys. Lett. 2001 346 233-240.
30. S. M. Andrade S. M. B. Costa R. Pansu Structural changes in w/o Triton X-100/cyclohexane–hexanol/water microemulsions probed by a fluorescent drug Piroxicam J. Colloid Interface Sci. 2000 226 260-268.
31. N. J. L. Roth A. C. Craig Predicted observable fluorescent lifetimes of several cyanines J. Phys. Chem. 1974 78 1154-1155.
32. J. Arden-Jacob N. J. Marx K. H. Drexhage New fluorescent probes for the red spectral region J. Fluoresc. 1997 7 91S-93S (supplement).
33. Y. E. Borisevich A. S. Tatikolov V. A. Kuzmin Flash photolysis instrument with the flash time of 1.5 μs Khim. Vys. Energ. 1978 474-475.
34. P. P. Levin S. M. B. Costa L. F. V. Ferreira J. M. Lopes F. R. Ribeiro Delayed fluorescence induced by molecular oxygen quenching of zinc tetraphenylporphyrin triplets at gas/solid interfaces of silica and zeolite J. Phys. Chem. B 1997 101 1355-1363.
35. G. Ponterini F. Momicchioli Trans–cis photoisomerization mechanism of carbocyanines: experimental check of theoretical models Chem. Phys. 1991 151 111-126.
36. V. Khimenko A. K. Chibisov H. Görner Effects of alkyl substituents in the polymethine chain on the photoprocesses in thiacarbocyanine dyes J. Phys. Chem. A 1997 101 7304-7310.
37. D. Noukakis M. Van der Auweraer S. Toppet F. C. De Schryver Photophysics of a thiacarbocyanine dye in organic solvents J. Phys. Chem. 1995 99 11860-11866.
38. A. M. Vinogradov A. S. Tatikolov S. M. B. Costa The effect of anionic, cationic and neutral surfactants on the photophysics and isomerization of 3,3′-diethylthiacarbocyanine Phys. Chem. Chem. Phys. 2001 3 4325-4332.
39. P. F. Aramendía R. M. Negri E. San Román Temperature dependence of fluorescence and photoisomerization in symmetric carbocyanines. Influence of medium viscosity and molecular structure J. Phys. Chem. 1994 98 3165-3173.
40. P. Mukherjee and K. Mysels, Critical Micelle Concentration of Surfactant Systems, National Bureau of Standards Reference Data Series, National Bureau of Standards, Washington, 1971.
41. J. C. Scaiano, CRC Handbook of Organic Photochemistry, Vol. 2, CRC Press, Boca Raton, 1989.
42. M. Y. Anikovsky A. S. Tatikolov V. A. Kuzmin Complex formation between 3,3′-diethylthiacarbocyanine iodide and DNA and its investigation in aqueous solution Int. J. Photoenergy 1999 1 29-33.
43. M. Y. Anikovsky, A. S. Tatikolov and V. A. Kuzmin, unpublished results.
44. S. De Boer K. J. Vink D. A. Wiersma Optical dynamics of condensed molecular aggregates: an accumulated photon-echo and hole-burning study of the J-aggregate Chem. Phys. Lett. 1987 137 99-106.
45. B. Kopainsky W. Kaiser Ultrafast transient processes of monomers, dimers and aggregates of pseudoisocyanine chloride (PIC) Chem. Phys. Lett. 1982 88 357-361.
46. V. Sundström T. Gillbro R. A. Gadonas A. Piskarskas Annihilation of singlet excitons in J aggregates of pseudoisocyanine (PIC) studied by pico- and subpicosecond spectroscopy J. Chem. Phys. 1988 89 2754-2762.
47. A. S. Tatikolov S. M. B. Costa Photophysical and aggregation properties of a long-chain squarylium indocyanine dye J. Photochem. Photobiol., A 2001 140 147-156.
48. C. Rullière Laser action and photoisomerisation of 3,3′-diethyl oxadicarbocyanine iodide (DODCI): influence of temperature and concentration Chem. Phys. Lett. 1976 43 303-308.
49. S. P. Velsko G. R. Fleming Solvent influence on photochemical isomerizations: photophysics of DODCI Chem. Phys. 1982 65 59.
50. S. K. Rentsch R. A. Gadonas A. Piskarskas Picosecond spectroscopic study of the influence of the solvent on the photoisomerization and relaxation of a streptocyanine dye Chem. Phys. Lett. 1984 104 235-239.
51. E. Åkesson V. Sundström T. Gillbro Isomerization dynamics in solution described by Kramers’ theory with a solvent-dependent activation energy Chem. Phys. 1986 106 269-280.