Rotational diffusion of the 7-diethylamino-4-methylcoumarin C1 dye molecule in polar protic and aprotic solvents

Photochemical and Photobiological Sciences

Volumn 2, Issue 3, 2003, Pages 329-341

  Gustavsson, T ^a   Cassara, L ^a   Marguet, S ^a   Gurzadyan, G ^a,b   Van Der Meulen, P ^a,c   Pommeret, S ^a   Mialocq, J C ^a  

^a CEA SACLAY   (France)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

7 DIETHYLAMINO 4 METHYLCOUMARIN; ALCOHOL DERIVATIVE; COUMARIN DERIVATIVE; DYE; SOLVENT; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; DIFFUSION; FLUORESCENCE; HYDRODYNAMICS; HYDROGEN BOND; PRIORITY JOURNAL; VISCOSITY;

EID: 20544440282     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b211755j     Document Type: Article

References (114)

1. K. B. Eisenthal and K. H. Drexhage, Measurement of orientational relaxation using picosecond light pulses, J. Chem. Phys., 1969, 51, 5720-5721.
2. T. J. Chuang and K. B. Eisenthal, Studies of effects of hydrogen bonding on orientational relaxation using picosecond light pulses, Chem. Phys. Lett., 1971, 11, 368-370.
3. P. Debye, Polar Molecules, Dover Publications, London, 1929.
4. G. R. Fleming, Chemical Applications of Ultrafast Spectroscopy, Oxford University Press, 1986.
5. D. R. Bauer, J. I. Brauman and R. Pecora, Molecular reorientation in liquids. Experimental test of hydrodynamic models, J. Am. Chem. Soc., 1974, 96, 6840-6843.
6. G. T. Evans and D. Kivelson, The orientational-correlation time intercept in liquids, J. Chem. Phys., 1986, 84, 385-390.
7. F. Perrin, Mouvement Brownien d'un ellipsoide (I). Dispersion diélectrique pour des molécules ellipsoidales, J. Phys. Paris, 1934, 5, 497.
8. T. Tao, Time-dependent fluorescence depolarization and Brownian rotational diffusion coefficients of macromolecules, Biopolymers, 1969, 8, 609-632.
9. C. M. Hu and R. Zwanzig, Rotational friction coefficients for spheroids with the slipping boundary condition, J. Chem. Phys., 1974, 60, 4354-4357.
10. G. K. Youngren and A. Acrivos, Rotational friction coefficients for ellipsoids and chemical molecules with the slip boundary condition, J. Chem. Phys., 1975, 63, 3846-3848.
11. G. R. Fleming, J. M. Morris and G. W. Robinson, Direct observation of rotational diffusion by picosecond spectroscopy, Chem. Phys., 1976, 17, 91-100.
12. G. Porter, P. J. Sadkowski and C. J. Tredwell, Picosecond rotational diffusion in kinetic and steady state fluorescence spectroscopy, Chem. Phys. Lett., 1977, 49, 416-420.
13. K. G. Spears and L. E. Cramer, Rotational diffusion in aprotic and protic solvents, Chem. Phys., 1978, 30, 1-8.
14. D. P. Millar, R. Shah and A. H. Zewail, Picosecond saturation spectroscopy of cresyl violet: Rotational diffusion by a "sticking" boundary condition in the liquid, Chem. Phys. Lett., 1979, 66, 435-440.
15. R. W. Wijnaendts van Resandt and L. de Maeyer, Picosecond rotational diffusion by differential single-photon fluorescence spectroscopy, Chem. Phys. Lett., 1981, 78, 219-223.
16. G. S. Beddard, T. Doust and J. Hudales, Structural Features in ethanol-water mixtures revealed by picosecond fluorescence anisotropy, Nature, 1981, 294, 145.
17. D. H. Waldeck and G. R. Fleming, Influence of viscosity and temperature on rotational reorientation. Anisotropic absorption studies of 3,3′-diethyloxadicarbocyanine iodide, J. Phys. Chem., 1981, 85, 2614-2617.
18. L. A. Philips, S. P. Webb and J. H. Clark, High-pressure studies of rotational reorientation dynamics: The role of dielectric friction, J. Chem. Phys., 1985, 83, 5810-5821.
19. G. J. Blanchard and M. J. Wirth, Anomalous temperature-dependent reorientation of cresyl violet in 1-dodecanol, J. Phys. Chem., 1986, 90, 2521-2525.
20. E. F. Gudgin Templeton and G. A. Kenney-Wallace, Correlation between molecular reorientation dynamics of ionic probes in polar fluids and dielectric friction by picosecond modulation spectroscopy, J. Phys. Chem., 1986, 90, 5441-5448.
21. 2O system, J. Phys. Chem., 1986, 90, 2896-2900.
22. M. Maroncelli and G. R. Fleming, Picosecond solvation dynamics of coumarin 153: the importance of molecular aspects of solvation, J. Chem. Phys., 1987, 86, 6221.
23. G. J. Blanchard, A study of the state-dependent reorientation dynamics of oxazine 725 in primary normal aliphatic alcohols, J. Phys. Chem., 1988, 92, 6303-6307.
24. G. J. Blanchard, State-dependent reorientation characteristics of methylene blue: The importance of dipolar solvent-solute interactions, J. Phys. Chem., 1989, 93, 4315-4319.
25. G. B. Dutt, S. Doraiswamy and N. Periasamy, Molecular reorientation dynamics of polar dye probes in tertiary-butyl alcohol-water mixtures, J. Chem. Phys., 1991, 94, 5360-5368.
26. G. Imeshev and L. R. Khundkar, Inhomogeneous rotational dynamics of a rodlike probe in 1-propanol, J. Chem. Phys., 1995, 103, 8322-8328.
27. A. Srivastava and S. Doraiswamy, Rotational diffusion of rose bengal, J. Chem. Phys., 1995, 103, 6197-6205.
28. E. F. Gudgin Templeton, E. L. Quitevis and G. A. Kenney-Wallace, Picosecond reorientational dynamics of resorufin: Correlation of dynamics and liquid structure, J. Phys. Chem., 1985, 89, 3238-3243.
29. K. G. Spears and K. M. Steinmetz, Solvent interactions with anions by reorientation studies of resorufin, J. Phys. Chem., 1985, 89, 3623-3629.
30. D. Ben-Amotz and T. W. Scott, Microscopic frictional forces on molecular motion in liquids. Picosecond rotational diffusion in alkanes and alcohols, J. Chem. Phys., 1987, 87, 3739-3748.
31. M. Roy and S. Doraiswamy, Rotational dynamics of nonpolar solutes in different solvents: Comparative evaluation of the hydrodynamic and quasihydrodynamic models, J. Chem. Phys., 1993, 98, 3213-3223.
32. M. A. Pereira, P. E. Share, M. J. Sarisky and R. M. Hochstrasser, Ultrafast rotational dynamics of electronically excited aniline molecules in solution from ultraviolet femtosecond fluorescence anisotropies, J. Chem. Phys., 1991, 94, 2513-2521.
33. R. S. Moog, D. L. Bankert and M. Maroncelli, Rotational diffusion of coumarin 102 in trifluorethanol: the case for solvent attachment, J. Phys. Chem., 1993, 97, 1496-1501.
34. Y. Jiang, P. K. McCarthy and G. J. Blanchard, The role of multiple electronic states in the dissipative energy dynamics of coumarin 153, Chem. Phys., 1994, 183, 249-267.
35. M. L. Horng, J. A. Gardecki and M. Maroncelli, Rotational dynamics of coumarin 153: time-dependent friction, dielectric friction, and other nonhydrodynamic effects, J. Phys. Chem. A, 1997, 101, 1030-1047.
36. T. Gustavsson, L. Cassara, V. Gulbinas, G. Gurzadyan, J.-C. Mialocq, S. Pommeret, M. Sorgius and P. van der Meulen, Femtosecond Spectroscopic Study of Relaxation Processes of Three Amino-Substituted Coumarin Dyes in Methanol and Dimethylsulfoxide, J. Phys. Chem. A, 1998, 102, 4229-4245.
37. L. Cassara, T. Gustavsson, S. Pommeret, J.-C. Mialocq, J. Chalom and A. Reveilleau, Ultrafast spectroscopic investigation of the relaxation dynamics of a new class of water-soluble coumarins, Fast Elementary Processes in Chemical anil Biological Systems, 1996, 364, 486-495.
38. P. Hébert, G. Baldacchino, T. Gustavsson and J.-C. Mialocq, Photochemistry of an unsymmetrical polymethine-cyanine dye; solute-solvent interactions and relaxation dynamics of LDS 751, J. Photochem. Photobiol. A: Chem., 1994, 84, 45-55.
39. D. V. O'Connor, V. Phillips, Time-correlated Single Photon Counting, Academic Press, 1984.
40. A. Jablonsky, Acta Phys. Pol., 1957, 16, 471.
41. M. J. Kamlet, J. L. Abboud and R. W. Taft, The solvatochromic comparison method. 6. The pi-scale of solvent polarities, J. Am. Chem. Soc., 1977, 99, 6027-6038.
42. M. J. Kamlet, J. L. Abboud, M. H. Abraham and R. W. Taft, Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, pi*, alpha, and beta, and some methods for simplifying the generalized solvatochromic equation, J. Org. Chem., 1983, 48, 2877-2887.
43. Y. Marcus, M. J. Kamlet and R. W. Taft, Linear solvation energy relationships. Standard molar Gibbs free energies and enthalpies of ions from water into nonaqueous solvents, J. Phys. Chem., 1988, 92, 3613-3622.
44. J. T. Edward, Molecular Volumes and the Stokes-Einstein equation, J. Chem. Educ., 1970, 47, 261-270.
45. K. Rotkiewicz, K. H. Grellman and Z. R. Grabowski, Reinterpretation of the anomalous fluorescence of p-N,N-dimethylaminobenzonitrile, Chem. Phys. Lett., 1973, 19, 315-318.
46. G. Jones II, W. R. Jackson, C. Choi and W. R. Bergmark, Solvent effects on emission yield and lifetime for coumarin laser dyes. Requirements for a rotary decay mechanism, J. Phys. Chem., 1985, 89, 294-300.
47. W. Rettig and A. Klock, Intramolecular fluorescence quenching in aminocoumarins. Identification of an excited state with full charge separation, Can. J. Chem., 1985, 63, 1649-1653.
48. T. Lopez Arbeloa, F. Lopez Arbeloa, M. J. Tapia and I. Lopez Arbeloa, Hydrogen-bonding effect on the photophysical properties of 7-aminocoumarin derivatives, J. Phys. Chem., 1993, 97, 4704-4707.
49. M. Diraison, P. Millié, S. Pommeret, T. Gustavsson and J.-C. Mialocq, Solvation structure of coumarin 1 in acetonitrile: the role of the electrostatic solute-solvent potential, Chem. Phys. Lett., 1998, 282, 152-158.
50. G. J. Blanchard, Picosecond spectroscopic measurement of a solvent dependent chance of rotational diffusion rotor shape, J. Chem. Phys., 1987, 87, 6802-6808.
51. S. K. Garg and C. P. Smyth, J. Phys. Chem., 1965, 69, 1294.
52. M. L. Horng, J. A. Gardecki, A. Papazyan and M. Maroncelli, Subpicosecond measurements of polar solvation dynamics: Coumarin 153 revisited, J. Phys. Chem., 1995, 99, 17311-17337.
53. N. Ito, O. Kajimoto and K. Hara, High-Pressure Studies of Rotational Dynamics for Coumarin 153 in Alcohols and Alkanes, J. Phys. Chem. A, 2002, 106, 6024-6029.
54. J. L. Dote, D. Kivelson and R. N. Schwartz, A molecular quasi-hydrodynamic free-space model for molecular rotational relaxation in liquids, J. Phys. Chem., 1981, 85, 2169-2180.
55. G. R. Fleming, A. E. W. Knight, J. M. Morris, R. J. Robbins and G. W. Robinson, Slip boundary conditions for molecular rotation: Time dependent fluorescence depolarization studies of BBOT, Chem. Phys. Lett., 1977, 51, 399-102.
56. G. R. Fleming, A. E. W. Knight, J. M. Morris, R. J. Robbins and G. W. Robinson, Rotational diffusion of the mode-locking dye DODCI and its photoisomer, Chem. Phys. Lett., 1977, 49, 1-7.
57. H. E. Lessing, A. von Jena and M. Reichert, Orientational aspect of transient absorption in solutions, Chem. Phys. Lett., 1975, 36, 517- 522.
58. A. von Jena and H. E. Lessing, Rotational-diffusion anomalies in dye solutions from transient-dichroism experiments, Chem. Phys., 1979, 40, 245-256.
59. A. von Jena and H. E. Lessing, Rotational diffuson of dyes in solvents of low viscosity from transient-dichroism experiments, Chem. Phys. Lett., 1981, 78, 187.
60. T.-W. Nee and R. Zwanzig, Theory of dielectric relaxation in polar liquids, J. Chem. Phys., 1970, 52, 6353-6363.
61. J. B. Hubbard and P. G. Wolynes, Dielectric friction and molecular reorientation, J. Chem. Phys., 1978, 69, 998-1006.
62. P. Madden and D. Kivelson, Dielectric friction and molecular reorientation, J. Phys. Chem., 1982, 86, 4244-4256.
63. D. S. Alavi and D. H. Waldeck, Rotational dielectric friction on a generalized charge distribution, J. Chem. Phys., 1991, 94, 6196-6202.
64. D. S. Alavi and D. H. Waldeck, Erratum: Rotational dielectric friction on a generalized charge distribution, J. Chem. Phys., 1993, 98, 3580-3581.
65. D. Kivelson and K. G. Spears, Dielectric friction as a source of rotational drag on charged noncentrosymmetric molecules, J. Phys. Chem., 1985, 89, 1999-2001.
66. J. D. Simon, Time-resolved studies of solvation in polar media, Acc. Chem. Res., 1988, 21, 128-134.
67. G. A. Kenney-Wallace, S. Paone and C. Kalpouzos, Femtosecond laser spectroscopy and dynamics of solvation in liquids and electrolytes, Faraday Discuss. Chem. Soc., 1988, 85, 185-198.
68. G. J. Blanchard, Detection of a transient solvent-solute complex using time-resolved pump-probe spectroscopy, Anal. Chem., 1989, 61, 2394-2398.
69. G. J. Blanchard, Counterion-dependent reorientation dynamics of an oxazine in polar protic and aprotic solvents, J. Phys. Chem., 1991, 95, 5293-5299.
70. J. D. Simon and P. A. Thompson, Spectroscopy and rotational dynamics of oxazine 725 in alcohols: A test of dielectric friction theories, J. Chem. Phys., 1990, 92, 2891-2896.
71. G. B. Dutt, S. Doraiswamy, N. Periasamy and B. Venkataraman, Rotational reorientation dynamics of polar dye molecular probes by picosecond laser spectroscopic technique, J. Chem. Phys., 1990, 93, 8498-8513.
72. G. B. Dutt and S. Doraiswamy, Picosecond reorientational dynamics of polar dye probes in binary aqueous mixtures, J. Chem. Phys., 1992, 96, 2475-2491.
73. D. S. Alavi, R. S. Hartman and D. H. Waldeck, A test of continuum models for dielectric friction. Rotational diffusion of phenoxazine dyes in dimethylsulfoxide, J. Chem. Phys., 1991, 94, 4509-4520.
74. D. S. Alavi, R. S. Hartman and D. H. Waldeck, The influence of wave vector dependent dielectric properties on rotational friction. Rotational diffusion of phenoxazine dyes, J. Chem. Phys., 1991, 95, 6770-6783.
75. R. S. Hartman, D. S. Alavi and D. H. Waldeck, An experimental test of dielectric friction models using the rotational diffusion of aminoanthraquinones, J. Phys. Chem., 1991, 95, 7872-7880.
76. R. S. Hartman, D. S. Alavi and D. H. Waldeck, An experimental test of dielectric friction models using the rotational diffusion of aminoanthraquinones. Erratum, J. Phys. Chem., 1993, 97, 12106.
77. R. S. Hartman, D. S. Alavi and D. H. Waldeck, Elucidating the molecular origins of solute/solvent friction, Isr. J. Chem., 1993, 33, 157-166.
78. R. S. Hartman and D. H. Waldeck, A test of dielectric models. Rotational diffusion of fluorenes in dimethyl sulfoxide, J. Phys. Chem., 1994, 98, 1386-1393.
79. E. L. Quitevis and M. L. Horng, Picosecond ground-state rotational diffusion of merocyanine 540 in polar solvents, J. Phys. Chem., 1990, 94, 5684-5688.
80. D. R. Bessire and E. L. Quitevis, Effects of temperature and viscosity on rotational diffusion of merocyanine 540 in polar solvents, J. Phys. Chem., 1994, 98, 13083-13092.
81. M. Levitus, R. M. Negri and P. F. Aramendia, Rotational relaxation of carbocyanines. Comparative study with the isomerization dynamics, J. Phys. Chem., 1995, 99, 14231-14239.
82. M. Maroncelli, Continuum estimates of rotational dielectric friction and polar solvation, J. Chem. Phys., 1997, 106, 1545-1555.
83. P. Madden and D. Kivelson, A consistent molecular treatment of dielectric phenomena, Adv. Chem. Phys., 1984, LVI, 467-566.
84. V. Friedrich and D. Kivelson, Theory of time-dependent polarization about an ion in an isotropic liquid, J. Chem. Phys., 1987, 86, 6425-6431.
85. A. Declémy and C. Rullière, Picosecond solvation dynamics: The role of the solvent microscopic relaxation time in highly polar aprotic solvents, Chem. Phys. Lett., 1988, 146, 1-6.
86. A. Declémy, C. Rullière and P. Kottis, Solvation dynamics studied by picosecond fluorescence: microscopic reorientation and longitudinal relaxation of the solvent, Laser Chem., 1990, 10, 413-429.
87. B. Bagchi, D. W. Oxtoby and G. R. Fleming, Theory of the time development of the Stokes shift in polar media, Chem. Phys., 1984, 86, 257-267.
88. P. K. McCarthy and G. J. Blanchard, AMI study of the electronic structure of coumarins, J. Phys. Chem., 1993, 97, 12205-12209.
89. C. Parkanyi, M. G. Antonius, J. J. Aaron, M. Buna, A. Tine and L. Cisse, Determination of the first excited singlet-state dipole moments of coumarins by the solvatochromic method, Spectrosc. Lett., 1994, 27, 439-449.
90. G. van der Zwan and J. T. Hynes, Time-dependent fluorescence solvent shifts, dielectric friction, and nonequilibrium solvation in polar solvents, J. Phys. Chem., 1985, 89, 4181-4188.
91. G. B. Dutt, M. K. Singh and A. V. Sapre, Rotational dynamics of neutral red: Do ionic and neutral solutes experience the same friction?, J. Chem. Phys., 1998, 109, 5994-6003.
92. G. B. Dutt and S. Raman, Rotational dynamics of coumarins: An experimental test of dielectric friction theories, J. Chem. Phys., 2001, 114, 6702-6713.
93. L. Reynolds, J. A. Gardecki, S. J. V. Frankland, M. L. Horng and M. Maroncelli, Dipole solvation in nondipolar solvents: experimental studies of reorganization energies and solvation dynamics, J. Phys. Chem., 1996, 100, 10337-10354.
94. L. Cassara, Etude femtoseconde de colorants laser solubles dans l'eau: les coumarines, PhD Thesis, Université Paris 6: Paris, 1996.
95. A. J. Cross and J. D. Simon, Rotational dynamics of a solvated dipole: A molecular dynamics study of dielectric friction, J. Chem. Phys., 1987, 86, 7079-7083.
96. M. Bruehl and J. T. Hynes, Dielectric friction and solvation dynamics: a molecular dynamics study, J. Phys. Chem., 1992, 96, 4068-4074.
97. A. Papazyan and M. Maroncelli, Rotational dielectric friction and dipole solvation: Tests of theory based on simulations of simple model solutions, J. Chem. Phys., 1995, 102, 2888-2919.
98. M. G. Kurnikova, D. H. Waldeck and R. D. Coalson, A molecular dynamics study of dielectric friction, J. Chem. Phys., 1996, 105, 628-638.
99. N. Balabai, A. Sukharevsky, I. Read, B. Strazisar, M. Kurnikova, R. S. Hartman, R. D. Coalson and D. H. Waldeck, Rotational diffusion of organic solutes: The role of dielectric friction in polar solvents and electrolyte solutions, J. Mol. Liq., 1998, 77, 37-60.
100. M. G. Kurnikova, N. Balabai, D. H. Waldeck and R. D. Coalson, Rotational relaxation in polar solvents. Molecular dynamics study of solute-solvent interaction, J. Am. Chem. Soc., 1998, 120, 6121-6130.
101. J. A. Riddick, W. B. Bunger, T. K. Sakano, Organic Solvents, Physical properties and methods of purification, Wiley Interscience, New York, 1986.
102. J. A. Dean, Lange's Handbook of Chemistry, 15th edition, McGraw-Hill, New York, 1999.
103. T. Shinomiya, Dielectric dispersion and intermolecular association for 28 pure liquid alcohols. The position dependence of hydroxyl group in the hydrocarbon chain, Bull. Chem. Soc. Jpn., 1989, 62, 908.
104. C. Magallanes, A. Catenaccio and H. Mechette, Relaxation time and viscosity of several n-alcohol/heptane systems, J. Mol. Liq., 1989, 40, 53.
105. F. F. Hanna and I. K. Hakim, Main dielectric dispersion region of mixtures of some long-chain alcohols with non-polar solvents, Z. Naturforsch., 1972, 27A, 1363.
106. T. Shinomiya, Dielectric relaxation and intermolecular association for 1-decanol. Temperature and dilution dependences of monomer and three hydrogen-bonded species, Bull. Chem. Soc. Jpn., 1989, 62, 2258.
107. J. Timmermans, Physico-chemical constants of pure organic compounds, Elsevier, New York, 1950.
108. C. Wohlfarth, Static dielectric constants of pure liquids and binary liquid mixtures, Springer-Verlag, Berlin, 1991.
109. J.-C. Mialocq, T. Gustavsson and S. Pommeret, Spectroscopic laser femtoseconde dans l'eau, milieu biologique, J. Phys. IV, 1999, 9, 101.
110. S. K. Pal, J. Peon and A. H. Zewail, Ultrafast decay and hydration dynamics of DNA bases and mimics, Chem. Phys. Lett., 2002, 363, 57-63.
111. J. Barthel, K. Bachhuber, R. Buchner and H. Hetzenauer, Dielectric spectra of some common solvents in the microwave region. Water and lower alcohols, Chem. Phys. Lett., 1990, 165, 369-373.
112. J. Barthel, K. Bachhuber, R. Buchner, J. B. Gill and M. Kleebauer, Dielectric spectra of some common solvents in the microwave region. Dipolar aprotic solvents and amides, Chem. Phys. Lett., 1990, 167, 62-66.
113. I. Kirschenbaum, Physical properties and analysis of heavy water, McGraw-Hill, New York, 1951.
114. L. M. Mukherjee and E. Grunwald, Physical properties and hydrogen bonding in the system ethanol-2,2,2-trifluoroethanol, J. Phys. Chem., 1958, 62, 1311.