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Fluorescence Probes Based on Twisted Intramolecular Charge Transfer (TICT) States and Other Adiabatic Photoreactions

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Topics in Fluorescence Spectroscopy

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References

  1. T. M. Li and R. F. Parrish, Fluorescence and immunodiagnostic methods, in: Topics in Fluorescence Spectroscopy, Vol. 3 (J. R. Lakowicz, ed.), pp. 273–288, Plenum Press, New York (1992).

    Google Scholar 

  2. R. Rigler, J. Widengren, and Ü. Mets, Interactions and kinetics of single molecules as observed by fluorescence correlation spectroscopy, in: Fluorescence Spectroscopy, New Methods and Applications (O. S. Wolfbeis, ed.), pp. 13–24, Springer-Verlag, Berlin (1993).

    Google Scholar 

  3. H. Szmacinski and J. R. Lakowicz, Lifetime-based sensing, in: Topics in fluorescence Spectroscopy, Vol. 4 (J. R. Lakowicz, ed.), pp. 295–334, Plenum Press, New York (1994).

    Google Scholar 

  4. D. J. Cowley, Polar pocket with nonpolar lining, Nature 319, 14 (1986).

    Article  Google Scholar 

  5. P. Fromherz, K. H. Dambacher, H. Ephardt, A. Lambacher, C. O. Müller, R. Neigl, H. Schaden, O. Schenk, and T. Vetter, Fluorescent dyes as probes of voltage transients in neuron membranes. Progress report, Ber. Bunsenges. 95, 1333 (1991).

    CAS  Google Scholar 

  6. A. P. Jackson, M. P. Timmerman, C. R. Bagshaw, and C. C. Ashley, The kinetics of calcium binding to Fura-2 and Indo-1, FEBS Lett. 216, 35–39 (1987).

    Article  CAS  PubMed  Google Scholar 

  7. T. Förster, Fluoreszenz Organischer Verbindungen, Verlag Vandenhoeck & Ruprecht, Göttingen (1951).

    Google Scholar 

  8. N. J. Turro, J. McVey, V. Ramamurthy, and P. Lechtken, Adiabatische Photoreaktionen organischer Moleküle, Angew. Chem. 91, 597–612 (1979).

    CAS  Google Scholar 

  9. W. Rettig, Charge separation in excited states of decoupled systems-TICT compounds and implications regarding the development of processes and the development of new laser dyes and the primary processes of vision and photosynthesis, Angew. Chem. Int. Ed. Engl. 25, 971 (1986).

    Article  Google Scholar 

  10. H. Köppel, W. Domcke, and L. S. Cederbaum, Multimode molecular dynamics beyond the Born-Oppenheimer approximation, Adv. Chem. Phys. 57, 59–246 (1984).

    Google Scholar 

  11. W. Rettig and G. Wermuth, The kinetics of formation of twisted intramolecular charge transfer (TICT) states in p-substituted dialkylanilines: Consequences of conical intersections along the reaction coordinate, J. Photochem. 28, 351 (1985).

    Article  CAS  Google Scholar 

  12. W. Rettig, Solvent polarity dependent formation dynamics of TICT states. I. Differential solvato-kinetics, Ber. Bunsenges. Phys. Chem. 95, 259 (1991).

    CAS  Google Scholar 

  13. W. Rettig, Photoinduced electron transfer in twisted π-systems, in: Dynamics and mechanisms of Photoinduced Electron Transfer and Related Phenomena (N. Mataga, T. Okada, and H. Masuhara, eds.), pp. 57–69, Elsevier Science Publishers, Amsterdam (1992).

    Google Scholar 

  14. M. M. H. Khalil, N. Boens, M. Van Der Auweraer, M. Ameloot, R. Andriessen, J. Hofkens, and F. C. De Schryver, Compartimental analysis of the fluorescence decay surface of the exciplex formation between I-methylpyrene and triethylamine, J. Phys. Chem. 95, 9375–9381 (1991).

    Article  CAS  Google Scholar 

  15. J. Michl and V. Bonačič-Koutecký, Electronic Aspects of Organic Photochemistry, John Wiley & Sons, New York (1990).

    Google Scholar 

  16. M. Vogel and W. Rettig, Efficient intramolecular fluorescence quenching in triphenylmethane-dyes involving excited states with charge separation and twisted conformations, Ber. Bunsenges. Phys. Chem. 89, 962 (1985).

    CAS  Google Scholar 

  17. R. Lapouyade, K. Czeschka, W. Majenz, W. Rettig, E. Gilabert, and C. Rullière, Photophysics of donor-acceptor substituted stilbenes. A time-resolved fluorescence study using selectively bridged dimethylamino cyano model compounds, J. Phys. Chem. 96, 9643–9650 (1992).

    Article  CAS  Google Scholar 

  18. E. Lippert, W. Lüder, and H. Boos, Fluoreszenzspektrum und Franck-Condon-Prinzip in Lösungen Aromatischer Verbindungen, in: Advances in Molecular Spectroscopy (A. Mangini, ed.), p. 443, Pergamon Press, Oxford, England (1962).

    Google Scholar 

  19. Z. R. Grabowski, K. Rotkiewicz, A. Siemiarczuk, D. J. Cowley, and W. Baumann, Twisted intramolecular charge transfer states (TICT). A new class of excited states with a full charge separation, Now. J. Chim. (New J. Chem.) 3, 443 (1979).

    CAS  Google Scholar 

  20. K. Rotkiewicz, K. H. Grellmann, and Z. R. Grabowski, Reinterpretation of the anomalous fluorescence of P-N,N-dimethylamino-benzonitrile, Chem. Phys. Lett. 19, 315 (1973).

    Article  CAS  Google Scholar 

  21. K. Rotkiewicz, Z. R. Grabowsksi, A. Krowczynsksi, and W. Kühnle, Picosecond chemical relaxation of excited p-cyano-N,N-dialkylanilines, J. Lumin. 12, 877 (1976).

    Google Scholar 

  22. Z. R. Grabowski, K. Rotkiewicz, W. Rubaszewska, and E. Kirkor-Kaminska, Spectroscopy and kinetic of the twisted internal charge-transfer (TICT) excited state formation in p-substituted dialkylanilines, Acta Phys. Pol. A 54, 767 (1978).

    Google Scholar 

  23. Z. R. Grabowski, K. Rotkiewicz, and A. Siemiarczuk, Dual fluorescence of donor-acceptor molecules and the twisted intramolecular charge transfer (TICT) states, J. Lumin. 18, 420 (1979).

    Google Scholar 

  24. W. Rettig, Anwendungsaspekte adiabatischer Photoreaktionen, Nachr. Chem. Tech. Lab. 39, 298 (1991).

    Google Scholar 

  25. K. A. Al-Hassan and W. Rettig, Free volume sensing fluorescent probes, Chem. Phys. Lett. 126, 273 (1986).

    Article  CAS  Google Scholar 

  26. W. Rettig, R. Fritz, and J. Springer, Fluorescence probes based on adiabatic photochemical reactions, in: Photochemical Processes in Organized Molecular Systems (K. Honda, ed.), p. 61, Elsevier Science Publishers, Amsterdam (1991).

    Google Scholar 

  27. W. Rettig, Kinetic studies on fluorescence probes using synchrotron radiation, in: Fluorescence Spectroscopy: New Methods and Applications (O. S. Wolfbeis, ed.), pp. 31–47, Springer-Verlag, Berlin (1993).

    Google Scholar 

  28. R. A. Bissell, A. P. De Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, and K. R. A. S. Sandanayake, Molecular fluorescent signalling with ‘fluor-spacer-receptor’ systems: Approaches to sensing and switching devices via supramolecular photophysics, Chem. Soc. Rev., 187–195 (1992); (b) R. A. Bissell, A. P. De Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, C. P. McCoy, and K. R. A. S. Sandanayake, Fluorescnt PET (Photoinduced Electron Transfer) Sensors Top. Curr. Chem. 168, 223 (1993).

    Google Scholar 

  29. J. L. Habib Jiwan and J. P. Soumillion, Electron transfer photochemistry initiated from a twisted intramolecular charge transfer state used as an electron donor and as an acceptor, J. Photochem. Photobiol. A: Chem. 64, 145–158 (1992); J. P. Soumillion, Photoinduced electron transfer implying organic anions, in: Topics in Current Chemistry, Vol., Photoinduced Electron Transfer (J.Mattay, ed.), Springer Verlag, Berlin, pp. 93–141 (1993).

    Article  Google Scholar 

  30. G. Schopf, W. Rettig, and J. Bendig, Quenching of TICT fluorescence by electron donors, J. Photochem. Photobiol. A: Chem., in press.

    Google Scholar 

  31. Z. R. Grabowski and J. Dobkowski, Twisted intramolecular charge transfer (TICT) excited states: Energy and molecular structure, Pure Appl. Chem. 55, 245 (1983).

    CAS  Google Scholar 

  32. E. Lippert, W. Rettig, V. Bonačič-Koutecký, F. Heisel, and J. A. Miehé, Photophysics of internal twisting, Adv. Chem. Phys. 68, 1 (1987).

    CAS  Google Scholar 

  33. W. Rettig, Charge transfer in self-decoupling π-systems, in: Modern Models of Bonding and Delocalization, Serie: Molecular Structure and Energetics, Vol. 6 (J. F. Liebman and A. Greenberg, eds.), pp. 229–282, VCH Verlagsgesellschaft mbH, Weinheim, Germany (1988).

    Google Scholar 

  34. W. Rettig and W. Baumann, Luminescent and nonluminescent twisted intramolecularcharge transfer (TICT) states: Dipole moments and application, in: Photochemistry and Photophysics, Vol. 6 (J. F. Rabek, ed.), pp. 79–134, CRC Press, Boca Raton, Florida (1992).

    Google Scholar 

  35. M. Zander and W. Rettig, Fluorescence studies on solvent-induced intramolecular charge separation in symmetric biaryls, Chem. Phys. Lett. 110, 602 (1984).

    Article  CAS  Google Scholar 

  36. Th. Förster, Die pH-Abhängigkeit der Fluoreszenz von Naphthalinderivaten, Z Elektrochem. 54, 531–53 (1950).

    Google Scholar 

  37. J. Waluk, H. Bulska, A. Grabowska, and A. Mordzinski, Excited state proton transfer analysed by state-orbitals correlations, Nouv. J. Chim. (New J. Chem.) 10, 413 (1986).

    CAS  Google Scholar 

  38. F. Laermer, T. Elsaeser, and W. Kaiser, Femtosecond spectroscopy of excited-state proton-transfer in 2-(2’-hydroxyphenyl)benzothiazole, Chem. Phys. Lett. 148, 119 (1988).

    Article  CAS  Google Scholar 

  39. N. P. Ernsting, A. Mordzinski, and B. Dick, Excited-state intramolecular proton transfer in jet-cooled2,5-Bis-(2-benzothiazole)hydroquinone, J. Phys. Chem. 91, 1404 (1987); (b) B. Dick and N. P. Ernsting, Excited-state intramolecular proton transfer in 3-hydroxyflavone isolated in solid argon: Fluorescence and fluorescence-excitation spectra and tautomer fluorescence rise time. J. Phys. Chem. 91, 4261 (1987).

    Article  CAS  Google Scholar 

  40. S. Demmig and H. Langhals, Leichtlösliche, lichtechte Perylen-Fluoreszenzfarbstoffe, Ber. Bunsenges. Phys. Chem. 21, 225 (1988).

    Google Scholar 

  41. O. A. Salman and H. G. Drickamer, The effect of pressure and freezing on luminescence. I. 3-hydroxyflavone and indole, J. Chem. Phys. 77, 3329–3336 (1982).

    CAS  Google Scholar 

  42. H. Bulska, Intramolecular cooperative double proton transfer in (2,2’-bipyridyl)-3,3’-diol, Chem. Phys. Lett. 98, 398 (1983).

    Article  CAS  Google Scholar 

  43. P. Chou, D. McMorrow, T. J. Aartsma, and M. Kasha, The proton transfer laser. Gain spectrum and amplification of spontaneous emission of 3-hydroxyflavone. J. Phys. Chem. 88, 4596 (1984).

    Article  CAS  Google Scholar 

  44. J. Sepiol, H. Bulska, and A. Grabowska, The dihyodroxy derivative of 2,2’-bipyridyl as a new proton-transfer lasing dye, Chem. Phys. Lett. 140, 607 (1987).

    Article  CAS  Google Scholar 

  45. G. Woessner, G. Goeller, J. Rieker, H. Hoier, J. J. Stezowski, E. Daltrozzo, M. Neureiter, and H. E. A. Kramer, Ultraviolet stabilizers of the 2-(hydroxyphenyl)benzotriazole class-influence of the solvent on the absorption spectra and photochemical deactivation mechanism, J. Phys. Chem. 89, 3629–3636 (1985); (b) H. E. A. Kramer, The lightfastness or the non-photochemistry of dyes, Chimia 40, 160–169 (1986).

    Article  CAS  Google Scholar 

  46. D. Gormin and M. Kasha, Triple fluorescence in aminosalicylates. Modulation of normal proton-transfer and twisted intramolecular charge-transfer (TICT) fluorescence by physical and chemical perturbations, Chem. Phys. Lett. 153, 574 (1988).

    Article  CAS  Google Scholar 

  47. H. Beens and A. Weller, Excited molecular π-complexes in solution, in: Organic Molecular Photophysics, Vol. 2 (J. B. Birks, ed.), John Wiley & Sons, London (1975).

    Google Scholar 

  48. A. Weller, Singlet-and triplet-state exciplexes, in: The Exiplex (M. Gordon and W. R. Ware, eds.), p. 23, Academic Press, New York, San Francisco, London, (1975).

    Google Scholar 

  49. L. Bokobza, C. Pham-Van-Cang, L. Monnerie, J. Vandendriessche, and F. C. De Schryver, Investigation of the mobility of polybutadienes: 1. Excimer fluorescence technique, Polymer 30, 45 (1989).

    Article  CAS  Google Scholar 

  50. L. Bokobza, C. Pham-Van-Cang, C. Giordano, L. Monnerie, J. Vandendriessche and F. C. De Schryver, Relation between excimer formation in small probes and free-volume theory in polymer melts, Polymer 28, 1876 (1987).

    Article  CAS  Google Scholar 

  51. N. C. Yang, R. V. Carr, E. Li, J. K. McVey, and S. A. Rice, 2,3-Naphtho-2,5-bicyclo[2.2.0]hexadiene, J. Am. Chem. Soc. 96, 2297–2298 (1974); (b) R. V. Carr, B. Kim, J. K. McVey, N. C. Yang, W. Gerhartz, and J. Michl, Photochemistry and photophysics of 1,4-dewarnaphthalene, Chem. Phys. Lett. 39, 57–60 (1976).

    Article  CAS  Google Scholar 

  52. B. Jahn and H. Dreeskamp, Die photochemische Valenzisomerisierung 9-alkylsubstituierter Anthrazene zu 9,10-Dewarisomeren, Ber. Bunsenges. Phys. Chem. 88, 42–47 (1984).

    CAS  Google Scholar 

  53. K. Kemnitz, N. Tamai, I. Yamazaki, N. Nakashima, and K. Yoshihara, Site-dependent fluorescence lifetimes of isolated dye molecules adsorbed on organic single crystals and other substrates, J. Phys. Chem. 91, 1423–1430 (1987).

    Article  CAS  Google Scholar 

  54. A. Azzi, The application of fluorescent probes in membrane studies, Q. Rev. Biophysics 8, 237 (1975).

    CAS  Google Scholar 

  55. W. Nowak, P. Adamczak, A. Balter, and A. Sygula, J. Mol. Struct. (Theochem.) 139, 13 (1986); (b) J. Catalan, P. Perez, J. Laynez, and F. G. Blanco, Analysis of the solvent effect on the photophysics properties of 6-propianyl-2-(dimethylamino)naphthalene (PRODAN), J. Fluorescence 1, 215–233 (1991).

    Article  Google Scholar 

  56. R. B. Macgregor and G. Weber, Nature 319, 273 (1986).

    Article  Google Scholar 

  57. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum Press, New York (1983).

    Google Scholar 

  58. E. M. Kosower and D. Huppert, Excited state electron and proton transfers, Ann. Rev. Phys. Chem. 37, 127 (1986).

    Article  CAS  Google Scholar 

  59. W. Nowak and W. Rettig, Theoretical study of singlet excited states of donor-acceptor naphthalene derivatives, J. Mol. Struct. (Theochem.) 283, 1–12 (1993).

    Article  Google Scholar 

  60. A. A. Ayuk, W. Rettig, and E. Lippert, Temperature and viscosity effects on an excited state equilibrium as revealed from the dual fluorescence of very dilute solutions of 1-dimethylamino-4-cyanonaphthalene. Ber. Bansenges. Phys. Chem. 85, 553 (1981).

    CAS  Google Scholar 

  61. A. Nag and K. Bhattacharyya, Twisted intramolecular charge transfer emission of dimethylaminobenzonitrile in α-cyclodextrine cavities, Chem. Phys. Lett., 151, 474 (1988); (b) K. Bhattacharyya, Dual luminescence of dimethylaminobenzonitrile in γ-cyclodextrin, J. Chem. Soc. Faraday Trans. 86, 53 (1988).

    Article  CAS  Google Scholar 

  62. K. Bhattacharyya and M. Chowdhury, Environmental and magnetic field effects on exciplex and twisted charge transfer emission. Chem. Rev. 93, 507–535 (1993).

    Article  CAS  Google Scholar 

  63. G. S. Cox, P. J. Hauptmann, and N. J. Turro, Photochem. Photobiol. 39, 597 (1984).

    CAS  Google Scholar 

  64. O. S. Khalil and A. J. Sonessa, Critical micelle concentration. Fluorescence of 4-dimethylaminobenzonitrile in surfactant solutions, Mol. Photochem. 8, 399 (1977).

    CAS  Google Scholar 

  65. W. Rettig, F. Marschner, Molecular conformation and biradicaloid charge transfer states in substituted N-phenyl-pyrroles, New J. Chem. 14, 819 (1990).

    CAS  Google Scholar 

  66. K. Rotkiewicz and W. Rubaszewska, Intramolecular charge transfer state and unusual fluorescence from an upper excited singlet of a nonplanar derivative of p-cyano-N,N-dimethylaniline, J. Lumin. 27, 221 (1982).

    CAS  Google Scholar 

  67. W. Rettig and R. Gleiter, Dependence of intramolecular rotation in p-cyano-N,N-dialkylanilines on the twist angle. A fluorescence, UV absorption, and photoelectron spectroscopic study. J. Phys. Chem. 89, 4676 (1985).

    Article  CAS  Google Scholar 

  68. W. Rettig, G. Wermuth, and E. Lippert, Photophysical primary processes in solutions of p-substituted dialkylanilines, Ber. Bunsenges. Phys. Chem. 83, 692 (1979).

    CAS  Google Scholar 

  69. J. Hicks, M. Vandersall, Z. Babarogic, and K. B. Eisenthal, The dynamics of barrier crossings in solution: The effect of a solvent polarity-dependent barrier, Chem. Phys. Lett. 116, 18–24 (1985).

    Article  CAS  Google Scholar 

  70. H. Ephardt and P. Fromherz, Fluorescence and photoisomerization of an amphiphilic aminostilbazolium dye as controlled by the sensitivity of radiationless deactivation to polarity and viscosity, J. Phys. Chem. 93, 7717–7725 (1989).

    Article  CAS  Google Scholar 

  71. H. Ephardt and P. Fromherz, J. Phys. Chem. 93, 7717 (1986).

    Google Scholar 

  72. P. Fromherz and A. Heilemann, Twisted internal charge transfer in (aminophenyl)pyridinium. J. Phys. Chem. 96, 6864–6866 (1992).

    Article  CAS  Google Scholar 

  73. L. B. Cohen, B. M. Salzberg, H. V. Davila, W. N. Ross, D. Landowne, A. S. Waggoner, and C. H. Wang, Changes in axon fluorescence during activity: Molecular probes of membrane potential, J. Membrane Biol. 19, 1 (1974).

    Article  CAS  Google Scholar 

  74. R. K. Gupta, B. M. Salzber, A. Grinvald, L. B. Cohen, K. Kamino, S. Lesher, M. B. Boyle, A. S. Waggoner, and C. H. Wang, Improvements in optical methods for measuring rapid changes in membrane potential, J. Membrane Biol. 58, 123 (1981).

    Article  CAS  Google Scholar 

  75. L. M. Loew, S. Scully, L. Simpson, and A. S. Waggoner, Evidence for a charge-shift electrochromic mechanism in a probe of membrane potential, Nature 281, 497 (1979).

    Article  CAS  PubMed  Google Scholar 

  76. A. M. Klock and W. Rettig, The excited-state behavior of donor-acceptor biphenyl and phenylanthracene: A comparative study, Polish J. Chem. 67, 1375–1388 (1993).

    CAS  Google Scholar 

  77. M. Van Damme, J. Hofkens, F. C. De Schryver, T. G. Ryan, W. Rettig, and A. M. Klock, Solvent dynamics and twisted intramolecular charge transfer in 4-cyano-4’butyloxybiphenyl (4COB), Tetrahedron 45, 4693–4706 (1989).

    Google Scholar 

  78. V. Bonačič-Koutecký, J. Koutecký, and J. Michl, Neutrale und geladene Diradikale, Zwitterionen, Trichter auf der SI-Hyperpläche und Protonentranslokation; ihre Bedeutung für den Sehvorgang und andere photochemische und photophysikalische Prozesse, Angew. Chem. 99, 216 (1987); Angew. Chem. Int. Ed. Engl. 27, 170 (1987).

    Google Scholar 

  79. V. Bonacic-Koutecky and J. Michl, Charge-transfer-biradical excited states: Relation to anomalous fluorescence, “Negative” S1-T1 splitting in twisted aminoborane, J. Am. Chem. Soc. 107, 1765 (1985).

    Article  CAS  Google Scholar 

  80. W. Rettig and W. Baumann, Luminescent and nonluminescent twisted intramolecular charge transfer (TICT) states: Dipole moments and applications, in: Photochemistry and Photophysics, Vol. 6 (J. F. Rabek, ed.), pp. 79–134, CRC Press, Boca Raton, Florida (1992).

    Google Scholar 

  81. W. Rettig, B. Strehmel, and W. Majenz, The exited states of stilbene and stilbenoid donor-acceptor dye systems. A theoretical study, Chem. Phys. 173, 525–537 (1993).

    Article  CAS  Google Scholar 

  82. M. Vogel and W. Rettig, Excited state dynamics of triphenylmethane-dyes used for investigation of microviscosity effects, Ber. Bunsenges. Phys. Chem. 91, 1241 (1987).

    CAS  Google Scholar 

  83. A. Spernol and K. Wirtz, Zur Mikroreibung in Flüssigkeiten, Z. Naturforsch. 8A, 522–532, 1953; (b) A. Gierer and K. Wirtz, Molekulare Theorie der Mikroreibung, Z. Naturforsch. 8A, 532–538 (1953).

    CAS  Google Scholar 

  84. M. L. Williams, R. F. Landel, and J. D. Ferry, Temperature dependence of relaxation mechanisms in amorphous polymers and other glass forming liquids, J. Am. Chem. Soc. 77, 3701–3707 (1955)

    CAS  Google Scholar 

  85. D. V. O’Connor and D. Phillips, Time-Correlated Single Photon Counting, Academic Press, New York (1984); (b) R. F. Steiner, Fluoresence anisotropy: Theory and applications, in: Topics in Fluorescence Spectroscopy, Vol. 2 (J. R. Lakowicz, ed.), Plenum, New York (1991), p. 1.

    Google Scholar 

  86. S. Canonica, A. A. Schmid, and U. P. Wild, The rotational diffusion of p-terphenyl and p-quater-phenyl in non-polar solvents, Chem. Phys. Lett. 122, 529–534 (1985).

    Article  CAS  Google Scholar 

  87. M. F. Winnick, Photophysics of preassociated pyrenes in aqueous polymer solution and in other organized media, Chem. Rev. 93, 587 (1993); (b) V. Ramamurthy (ed.), Photochemistry in Organized and Constrained Media, VCH Publishers, New York (1991); (c) J. F. Rabek (ed.), Progress in Photochemistry and Photophysies, Vol. 6, CRC Press, Boca Raton, Florida (1992).

    Google Scholar 

  88. L. Bokobza, C. Pham-Van-Cang, C. Giordano, L. Monnerie, J. Vandendriessche, and F. C. De Schryver, Studies of the mobility of probes in poly(propylene oxide): 2. Excimer fluoresence technique, Polymer 29, 251 (1988).

    Article  CAS  Google Scholar 

  89. L. Bokobza L, E. Pajot-Augy, L. Monnerie, A. Castallan, and H. Bouas-Laurent, Excimer fluorescence as a probe of mobility in bulk polymers, Polymer Pholochem. 5, 191 (1984).

    CAS  Google Scholar 

  90. E. Pajot-Augy, L. Bokobza, L. Monnerie, A. Castallan, and H. Bouas-Laurent, Mobility of macromolecular chains as studied by means of excimer fluoresence, Macromolecules 17, 1490 (1984).

    Article  CAS  Google Scholar 

  91. R. O. Loutfy and K. Yee Law, Spectrochemistry and spectroscopy of intramolecular charge-transfer complexes. N,N-dialkylaxinobenzylidenemalononitriles, J. Phys. Chem. 84, 2803 (1980).

    Article  CAS  Google Scholar 

  92. K. A. Al-Hassan and T. Azumi, The red edge effect as a tool for investigating the origin of the anomalous fluorescence band of 9,9’-bianthryl in rigid polar polymer matrices, Chem. Phys. Lett, 150, 344 (1988).

    Article  CAS  Google Scholar 

  93. D. Anwand, F. W. Müller, B. Strehmel, and K. Schiller, Determination of the molecular mobility and the free volume of thin polymeric films with fluorescence probes, Makromol. Chem. 192, 1981–1991 (1991).

    Article  CAS  Google Scholar 

  94. B. Strehmel, V. Strehmel, H. J. Timpe, and K. Urban, Time-resolved fluoresence measurements for the characterization of epoxy systems, Eur. Polym. J. 28, 525–533 (1992).

    CAS  Google Scholar 

  95. R. O. Loutfy, Fluoresence probes for polymer free-volume, Pure Appl. Chem. 58, 1239 (1986).

    CAS  Google Scholar 

  96. Z. A. Dreger, J. M. Lang, and H. G. Drickamer, High pressure study of flexible fluorescent dye molecules in solid polymeric media. III. p-N,N-dimethylaminobenzylidenemalononitrile (DMABNM)-reanalyzed. Chem. Phys., 169, 369–371 (1993).

    CAS  Google Scholar 

  97. S. Tazuke, R. Kun Guo, and R. Hayashe, How does the polymer main chain influence the side-chain mobility? A fluorescence probe study by means of twisted intramolecular charge-transfer phenomena, Macromolecules 21, 1046 (1988).

    Article  CAS  Google Scholar 

  98. S. Tazuke, R. K. Guo, and T. Ikeda, Time-resolved fluoresence spectroscopy of a twisted intramolecular charge transfer compound bonded to polymers, J. Phys. Chem. 94, 1408 (1990).

    Article  CAS  Google Scholar 

  99. R. Hayashi, S. Tazuke, and C. W. Frank, Twisted intramolecular charge-transfer phenomenon as a fluorescence probe of microenvironment. Effect of polymer concentration on local viscosity and microscopic polarity around a polymer chain of poly(methyl methacrylate), Macromolecules 20, 983 (1987).

    Article  CAS  Google Scholar 

  100. S. Tazuke and R. K. Guo, Effects of polymer microenvironment on the thermodynamics of the twisted intramolecular charge transfer fluorescence, Macromolecules 23, 719 (1990).

    CAS  Google Scholar 

  101. R. K. Guo and S. Tazuke, Microheterogeneity of local segment mobility in solid polymethacrylates as studied by a polymer-bound twisted intramolecular charge transfer chromophore, Macromolecules 22, 3286 (1989).

    CAS  Google Scholar 

  102. K. A. Al-Hassan and T. Azumi, The role of free volume in the twisted intramolecular charge transfer (TICT) emission of dimethylaminobenzonitrile and related compounds in rigid polymer matrices. Chem. Phys. Lett. 146, 121 (1988).

    Article  CAS  Google Scholar 

  103. K. A. Al-Hassan and T. Azumi, Fluorescence decay characteristics of 4-dimethylaminobenzontrile in different polymer matrices: A time-resolved study in the nanosecond range, Chem. Phys. Lett. 163, 129 (1989).

    Article  CAS  Google Scholar 

  104. L. F. Lindoy, in: Mixed-donor macrocycles: solution and structural aspects of their complexation with transition and post-transition ions, Cation Binding by Macrocycles (Y. Inoue and G. W. Gokel, eds.), p. 599, Marcel Dekker, New York (1990).

    Google Scholar 

  105. M. Vogel, W. Rettig, R. Sens, and K. H. Drexhage, Structural relaxation of rhodamine dyes with different N-substitution patterns: A study of fluorescence decay times and quantum yields. Chem. Phys. Lett. 147, 452–460 (1988).

    CAS  Google Scholar 

  106. C. J. Tredwell and A. D. Osborne, Viscosity dependent internal conversion in the thodamine dye, fast acid violet 2R, J. Chem. Soc. Faraday Trans. II 76, 1627 (1980).

    CAS  Google Scholar 

  107. W. Rettig, Kinetic studies on fluorescence probes using synchrotron radiation, in: Fluorescence Spectroscopy. New Methods and Applications (O. S. Wolfbeis, ed.), pp. 31–47, Springer-Verlag, Berlin (1993).

    Google Scholar 

  108. P. Plaza, N. Dai Hung, M. M. Martin, Y. H. Meyer, M. Vogel, and W. Rettig, Ultrafast internal charge transfer in a donor-modified rhodamine, Chem. Phys. 168, 365–373 (1992).

    Article  CAS  Google Scholar 

  109. S. G. Schulman and J. D. Winefordner, Influence of pH in fluorescence and phosphorescence spectrometric analysis, Talanta 17, 607–616 (1970).

    Article  CAS  Google Scholar 

  110. Z. R. Grabowski and A. Grabowska, The Förster cycle reconsidered, Z. Phys. Chem. (Wiesbaden) 101, 197–208 (1976).

    CAS  Google Scholar 

  111. E. Van Der Donckt, Acid-base-properties of excited states, Prog. React. Kinet. 5, 273–299 (1970).

    Google Scholar 

  112. J. F. Ireland and P. A. H. Wyatt, Acid-base-properties of electronically excited states of organic molecules. Adv. Phys. Org. Chem. 12, 131 (1976).

    CAS  Google Scholar 

  113. A. Weller, Fast reactions of excited molecules, Prog. React. Kinet. 1, 187–214 (1961).

    CAS  Google Scholar 

  114. G. Jackson and G. Porter, Acidity constants in the triplet state, Proc. R. Soc. Land. Ser. A 260, 13–30 (1961).

    Google Scholar 

  115. H. Shizuka, Excited state proton-transfer reactions and proton-induced quenching of aromatic compounds, Acc. Chem. Res. 18, 141–147 (1985).

    Article  CAS  Google Scholar 

  116. M. Orrit and J. Bernard, Single pentacene molecules detected by fluorescence excitation in a p-terphenyl crystal, Phys. Rev. Lett. 65, 2716–2719 (1990).

    Article  CAS  PubMed  Google Scholar 

  117. L. Kador, D. E. Home, and W. E. Moerner, Optical detection and probing of single dopant molecules of pentacene in a p-terphenyl host crystal by means of absorption spectroscopy, J. Phys. Chem. 94, 1237–1248 (1990).

    Article  CAS  Google Scholar 

  118. R. J. Gillies and R. Martinez-Zaguilan, Regulation of intracellular pH in BALB/c 3T3 cells, J. Biol. Chem. 266, 1551–1556 (1991).

    CAS  PubMed  Google Scholar 

  119. R. A. Bissell, E. Calle, A. P. De Silva, S. A. De Silva, H. Q. N. Gunaratne, J. L. Habib-Jiwan, S. L. A. Peiris, R. A. D. D. Rupasinghe, T. K. S. D. Smarasinghe, K. R. A. S. Sandanayake, and J. P. Soumillion, Luminescence and charge transfer. Part 2. Aminomethyl anthracene derivatives as fluorescent PET (photoinduced electron transfer) sensors for protons, J. Chem. Soc. Perkin Trans. 2, 1559–1564 (1992).

    Google Scholar 

  120. J. E. Whitaker, R. P. Haughland, and F. G. Prendergast, Spectral and photophysical studies of benzo[c]xanthene dyes: Dual emission pH sensors, Anal. Biochem. 194, 330–344 (1991).

    Article  CAS  PubMed  Google Scholar 

  121. G. Grynkiewicz, M. Poenie, and R. Y. Tsien, A new generation of Ca2+ indicators with greatly improved fluorescence properties. J. Biol. Chem. 260, 3440–3450 (1985).

    CAS  PubMed  Google Scholar 

  122. W. Rettig and A. Klock, Intramolecular fluorescence quenching in aminocoumarines: Identification of an excited state with full charge separation, Can. J. Chem. 63, 1649–1653 (1985).

    CAS  Google Scholar 

  123. S. A. Jonker, F. Ariese, and J. W. Verhoeven, Cation complexation with functionalized 9-arylacridinium ions: Possible applications in the development of cation-selective optical probes, Rec. Trav. Chim. Pays-Bas 108, 109–115 (1987).

    Google Scholar 

  124. W. Rettig, W. Majenz, R. Lapouyade, and G. Haucke, Multidimensional photochemistry in flexible dye systems, J. Photochem. Photobiol. A: Chem. 62, 415–427 (1992).

    Article  CAS  Google Scholar 

  125. W. Rettig and W. Majenz, Competing adiabatic photoreaction channels in stilbene derivatives, Chem. Phys. Lett. 143, 335–341 (1989).

    Google Scholar 

  126. J. F. Letard, R. Lapouyade, and W. Rettig, Structure-photophysics correlations in a series of 4-(dialkylamino) stilbenes: Intramolecular charge transfer in the excited state as related to the twist around the single bonds, J. Am. Chem. Soc. 115, 2441–2447 (1993).

    Article  CAS  Google Scholar 

  127. K.J. Smit and K. P. Ghiggino, Effect of solvent on the photochemistry of trans-4,4’-diaminostilbene-2,2’-disulphonic acid, J. Photochem. 34, 23–34 (1986).

    Article  CAS  Google Scholar 

  128. J. F. Letard, R. Lapouyade, and W. Rettig, Relaxation pathways in photoexcited electron-rich stilbenes (D-D stilbenes) as compared to D-A stilbenes, Chem. Phys. Lett. 222, 209–216 (1994).

    CAS  Google Scholar 

  129. A. Z. Weller, Photoinduced electron transfer in solution: Exciplex and radical ion pair formation free enthalpies and their solvent dependence, Z. Phys. Chem. Neue Folge, Wiesbaden 133, 93–98 (1982).

    CAS  Google Scholar 

  130. R. Grigg and W. D. J. A. Norbert, Luminescent pH sensors based on di(2,2’-bipyridyl) (5,5’-diaminomethyl-2,2’-bipyridyl)ruthenium (II) complexes, J. Chem. Soc. Chem. Commun. 1300–1302 (1992).

    Google Scholar 

  131. H. G. Lohr and F. Vögtle, Chromo-and fluoroionophores. A new class of dye reagents. Acc. Chem Res. 18, 65–72 (1985).

    Google Scholar 

  132. J. F. Letard, R. Lapouyade, and W. Rettig, Synthesis and photophysical study of 4-(N-monoaza-15-crown-5)stilbenes forming TICT states and their complexation with cations, Pure Appl. Chem. 65, 1705–1712 (1993).

    CAS  Google Scholar 

  133. J. Bourson and B. Valeur, Ion-responsive fluorescent compounds. 2. Cation-steered intramolecular charge transfer in a crowned merocyanine, J. Phys. Chem. 93, 3871–3876 (1989).

    Article  CAS  Google Scholar 

  134. R. Y. Tsien, New calcium indicators and buffers with high selectivity against magnesium and protons: Design, synthesis and properties of prototype structure, Biochemistry 19, 2396–2404 (1980).

    Article  CAS  PubMed  Google Scholar 

  135. A. Minta, J. P. Y. Kao, and R. Y. Tsien, Fluorescent indicators for cytosolic calcium based on rhodamine and fluorescein chromophores, J. Biol. Chem. 264, 8171–8178 (1989).

    CAS  PubMed  Google Scholar 

  136. A. Minta and R. Y. Tsien, Fluorescent indicators for cytosolic sodium, J. Biol. Chem. 264, 19449–19457 (1989); (b) A. P. Jackson, M. P. Timmerman, C. R. Bagshaw, and C. C. Ashley, The kinetics of calcium binding to Fura-2 and Indo-1. FEBS Lett. 216, 35–39 (1987); (c) W. H. Wier, M. B. Cannell, J. R. Berlin, E. Marban, and W. J. Lederer, Cellular and subcellular heterogeneity of [Ca2+]1 in single heart cells revealed by Fura-2, Science 235, 325–328 (1987).

    CAS  PubMed  Google Scholar 

  137. D. B. Mac Queen and K. S. Schanze, Cation-controlled photophysics in a Re(I) fluoroionophore, J. Am. Chem. Soc. 113, 6108–6110 (1991).

    Google Scholar 

  138. J. Bourson, J. Pouget. and B. Valeur, Ion-responsive fluorescent compounds. 4. Effect of cation binding on the photophysical properties of a coumarin linked to monoaza-and diazacrown ethers, J. Phys. Chem. 97, 4552–4557 (1993).

    Article  CAS  Google Scholar 

  139. J. F. Letard and R. Lapouyade, to be published.

    Google Scholar 

  140. M. M. Martin, P. Plaza, N. Dai Hung, Y. H. Meyer, J. Bourson, and B. Valeur, Photoejection of cations from complexes with a crown-ether-linked merocyanine evidenced by ultrafast spectroscopy, Chem. Phys. Lett. 202, 425–430 (1993).

    Article  CAS  Google Scholar 

  141. S. R. Adams, J. P. Y. Kao, and R. Y. Tsien, Biologically useful chelators that take up Ca2+ upon illumination. J. Am. Chem. Soc. 111, 7957–7968 (1989).

    CAS  Google Scholar 

  142. D. Braun, R. Lapouyade, and W. Rettig (in preparation).

    Google Scholar 

  143. W. Rettig, Photoinduced charge separation via twisted intramolecular charge transfer states, in Topics in Current Chemistry, Vol. 169: Electron Transfer I (J. Mattay, ed.), pp. 253–299, Springer Verlag, Berlin (1994).

    Google Scholar 

  144. W. Rettig, W. Majenz, R. Lapouyade, and M. Vogel, Adiabatic photochemistry with luminescent products, J. Photochem. Photobiol. A: Chem. 65, 95–110 (1992).

    Article  CAS  Google Scholar 

  145. J. Dobkowski, W. Rettig, B. Paeplow, K. H. Koch, K. Müllen, R. Lapouyade, and Z. R. Grabowski, Intramolecular charge transfer states in symmetric biaryls. The unusual case of biperylenyl, New J. Chem. 18, 525–533 (1994).

    CAS  Google Scholar 

  146. R. Zahradnik and J. Fabian, Auf der Suche nach tieffarbigen organischen Verbindungen, Angew. Chem. 101, 693 (1989).

    Google Scholar 

  147. V. Bonačič-Koutecký, K. Schöffel, and J. Michl, Electronic states of cyclobutadiene heteroanalogues. Critical biradicaloids, J. Am. Chem. Soc. 111, 6140 (1989).

    Google Scholar 

  148. V. Kamat, S. Das, K. G. Thomas, and M. V. George, Photochemistry of squaraine dyes. 1. Excited singlet, triplet, and redox states of bis[4-(dimethylamino)phenyl]squaraine and bis[4-(dimethylamino)-2-hydroxyphenyl]squaraine. J. Phys. Chem. 96, 195–199 (1992).

    CAS  Google Scholar 

  149. K. Hamasaki, H. Ikeda, A. Nakamura, A. Ueno, F. Toda, I. Suzuki, and T. Osa, Fluorescence sensors of molecular recognition. Modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence, J. Am. Chem. Soc. 115, 5035–5040 (1993).

    Article  CAS  Google Scholar 

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  1. W. Nernst Institute for Physical and Theoretical Chemistry, Humboldt University at Berlin, D-10117, Berlin, Germany

    W. Rettig

  2. Photophysique et Photochimie Moléculaire, URA (CNRS) No. 348, Université de Bordeaux I, F-33405, Talence, France

    René Lapouyade

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  1. Center for Fluorescence Spectroscopy and Department of Biological Chemistry, University of Maryland School of Medicine, Baltimore, Maryland, USA

    Joseph R. Lakowicz

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Rettig, W., Lapouyade, R. (2002). Fluorescence Probes Based on Twisted Intramolecular Charge Transfer (TICT) States and Other Adiabatic Photoreactions. In: Lakowicz, J.R. (eds) Topics in Fluorescence Spectroscopy. Topics in Fluorescence Spectroscopy, vol 4. Springer, Boston, MA. https://doi.org/10.1007/0-306-47060-8_5

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