Proton Transfer Dynamics of 4'- N, N -Dimethylamino-3-hydroxyflavone Observed in hydrogen-bonding solvents and aqueous micelles

Journal of Physical Chemistry B

Volumn 119, Issue 17, 2015, Pages 5650-5661

  Ghosh, Deborin ^a   Batuta, Shaikh ^b   Das, Sreeparna ^b   Begum, Naznin Ara ^b   Mandal, Debabrata ^a  

^a UNIVERSITY OF CALCUTTA   (India)

^b VISVA BHARATI UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DYNAMICS; EXCITED STATES; FLAVONOIDS; FLUOROPHORES; LASER SPECTROSCOPY; MICELLES; MOLECULES; PHASE INTERFACES; PROTON TRANSFER; SOLVENTS;

EXCITED-STATE ENERGY SURFACES; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; INTERMOLECULAR HYDROGEN BONDS; MICELLE-WATER INTERFACE; PHOTOPHYSICAL STUDIES; SOLVATION DYNAMICS; SOLVENT RELAXATION; TIME-RESOLVED SPECTROSCOPY;

HYDROGEN BONDS;

EID: 84928969129     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/acs.jpcb.5b00021     Document Type: Article

References (53)

1. Schwartz, B. J.; Peteanu, L. A.; Harris, C. B. Direct Observation of Fast Proton Transfer: Femtosecond Photophysics of 3-Hydroxyflavone J. Phys. Chem. 1992, 96, 3591-3598
2. Ameer-Beg, S.; Ormson, S. M.; Brown, R. G.; Matousek, P.; Towrie, M.; Nibbering, E. T. J.; Foggi, P.; Neuwahl, F. V. R. Ultrafast Measurements of Excited State Intramolecular Proton Transfer (ESIPT) in Room Temperature Solutions of 3-Hydroxyflavone and Derivatives J. Phys. Chem. A 2001, 105, 3709-3718
3. Bader, A. N.; Pivovarenko, V. G.; Demchenko, A. P.; Ariese, F.; Gooijer, C. Excited State and Ground State Proton Transfer Rates of 3-Hydroxyflavone and Its Derivatives Studied by Shpol'skii Spectroscopy: The Influence of Redistribution of Electron Density J. Phys. Chem. B 2004, 108, 10589-10595
4. Strandjord, A. J. G.; Courtney, S. H.; Friedrich, D. M.; Barbara, P. F. Excited State Dynamics of 3-Hydroxyflavone J. Phys. Chem. 1983, 87, 1125-1133
5. McMorrow, D.; Kasha, M. Intramolecular Excited-State Proton Transfer in 3-Hydroxyflavone. Hydrogen-Bonding Solvent Perturbations J. Phys. Chem. 1984, 88, 2235-2243
6. Strandjord, A. J. G.; Barbara, P. F. Proton Transfer Kinetics of 3-Hydroxyflavone: Solvent Effects J. Phys. Chem. 1985, 89, 2355-2361
7. Strandjord, A. J. G.; Smith, D. E.; Barbara, P. F. Structural Effects on the Proton-Transfer Kinetics of 3-Hydroxyflavones J. Phys. Chem. 1985, 89, 2362-2366
8. Brucker, G. A.; Swinney, T. C.; Kelley, D. F. Proton-Transfer and Solvent Polarization Dynamics in 3-Hydroxyflavone J. Phys. Chem. 1991, 95, 3190-3195
9. Basu, S.; Mondal, S.; Mandal, D. Proton Transfer Reactions in Nanoscopic Polar Domains: 3-Hydroxyflavone in AOT Reverse Micelles J. Chem. Phys. 2010, 132, 034701-1-034701-6
10. Swinney, T. C.; Kelley, D. F. Proton Transfer Dynamics in Substituted 3-Hydroxyflavones: Solvent Polarization Effects J. Chem. Phys. 1993, 99, 211-221
11. Chou, P.-T.; Martinez, M. L.; Clements, J. H. Reversal of Excitation Behaviour of Proton-Transfer Vs. Charge-Transfer by Dielectric Perturbation of Electronic Manifolds J. Phys. Chem. 1993, 97, 2618-2622
12. Ormson, S. M.; Brown, R. G.; Vollmer, F.; Rettig, W. Switching between Charge- and Proton-Transfer Emission in the Excited State of a Substituted 3-Hydroqflavone J. Photochem. Photobiol., A 1994, 81, 65-72
13. Klymchenko, A. S.; Demchenko, A. P. Multiparametric Probing of Intermolecular Interactions with Fluorescent Dye Exhibiting Excited State Intramolecular Proton Transfer Phys. Chem. Chem. Phys. 2003, 5, 461-468
14. Roshal, A. D.; Organero, J. A.; Douhal, A. Tuning the Mechanism of Proton-Transfer in a Hydroxyflavone Derivative Chem. Phys. Lett. 2003, 379, 53-59
15. Klymchenko, A. S.; Pivovarenko, V. G.; Demchenko, A. P. Elimination of the Hydrogen Bonding Effect on the Solvatochromism of 3-Hydroxyflavones J. Phys. Chem. A 2003, 107, 4211-4216
16. Douhal, A.; Sanz, M.; Carranza, M. A.; Organero, J. A.; Santos, L. Femtosecond Observation of Intramolecular Charge- and Proton-Transfer Reactions in a Hydroxyflavone Derivative Chem. Phys. Lett. 2004, 394, 54-60
17. Ameer-Beg, S.; Ormson, S. M.; Poteau, X.; Brown, R. G.; Foggi, P.; Bussotti, L.; Neuwahl, F. V. R. Ultrafast Measurements of Charge and Excited-State Intramolecular Proton Transfer in Solutions of 4'-(N, N -Dimethylamino) Derivatives of 3-Hydroxyflavone J. Phys. Chem. A 2004, 108, 6938-6943
18. Pivovarenko, V. G.; Wroblewska, A.; Błazejowski, J. The Effect of Hydrogen Bonding Interactions between 2-[4-(Dimethylamino)Phenyl]-3-Hydroxy-4 H -Chromene-4-One in the Ground and Excited States and Dimethylsulfoxide or Methanol on Electronic Absorption and Emission Transitions J. Mol. Struct. 2004, 708, 175-181
19. Chou, P.-T.; Pu, S.-C.; Cheng, Y.-M.; Yu, W.-S.; Yu, Y.-C.; Hung, F.-T.; Hu, W.-P. Femtosecond Dynamics on Excited-State Proton/Charge-Transfer Reaction in 4'- N, N -Diethylamino-3-Hydroxyflavone. The Role of Dipolar Vectors in Constructing a Rational Mechanism J. Phys. Chem. A 2005, 109, 3777-3787
20. Klymchenko, A. S.; Kenfack, C.; Duportail, G.; Mély, Y. Effects of Polar Protic Solvents on Dual Emissions of 3-Hydroxychromones J. Chem. Sci. 2007, 119, 83-89
21. Shynkar, V. V.; Mély, Y.; Duportail, G.; Piémont, E.; Klymchenko, A. S.; Demchenko, A. P. Picosecond Time-Resolved Fluorescence Studies Are Consistent with Reversible Excited-State Intramolecular Proton Transfer in 4'-(Dialkylamino)-3-Hydroxyflavones J. Phys. Chem. A 2003, 107, 9522-9529
22. Shynkar, V. V.; Klymchenko, A. S.; Piémont, E.; Demchenko, A. P.; Mély, Y. Dynamics of Intermolecular Hydrogen Bonds in the Excited States of 4'-Dialkylamino-3-Hydroxyflavones. On the Pathway to an Ideal Fluorescent Hydrogen Bonding Sensor J. Phys. Chem. A 2004, 108, 8151-8159
23. Organero, J. A.; Tormo, L.; Sanz, M.; Roshal, A.; Douhal, A. Complexation Effect of γ-Cyclodextrin on a Hydroxyflavone Derivative: Formation of Excluded and Included Anions J. Photochem. Photobiol., A 2007, 188, 74-82
24. Klymchenko, A. S.; Yushchenko, D. A.; Mély, Y. Tuning Excited State Intramolecular Proton Transfer in 3-Hydroxyflavone Derivative by Reaction of Its Isothiocyanate Group with an Amine J. Photochem. Photobiol., A 2007, 192, 93-97
25. Sanz, M.; Organero, J. A.; Douhal, A. Proton and Charge Transfer Reactions Dynamics of a Hydroxyflavone Derivative in a Polar Solvent and in a Cyclodextrin Nanocavity Chem. Phys. 2007, 338, 135-142
26. Nemkovich, N. A.; Kruchenok, J. V.; Rubinov, A. N.; Pivovarenko, V. G.; Baumann, W. Site Selectivity in Excited-State Intramolecular Proton Transfer in Flavonols J. Photochem. Photobiol., A 2001, 139, 53-62
27. Nemkovich, N. A.; Baumann, W.; Pivovarenko, V. G. Dipole Moments of 4'-Aminoflavonols Determined Using Electro-Optical Absorption Measurements or Molecular Stark-Effect Spectroscopy J. Photochem. Photobiol., A 2002, 153, 19-24
28. Nemkovich, N. A.; Pivovarenko, V. G.; Baumann, W.; Rubinov, A. N.; Sobshuk, A. N. Dipole Moments of 4γ-Aminoflavonol Fluorescent Probes in Different Solvents J. Fluoresc. 2005, 15, 29-36
29. Fukuda, M.; Terazima, M.; Kimura, Y. Study on the Excited State Intramolecular Proton Transfer of 4'-N,N-Diethylamino-3-Hydroxyflavone in Imidazolium-Based Room Temperature Ionic Liquids Chem. Phys. Lett. 2008, 463, 364-368
30. Kimura, Y.; Fukuda, M.; Suda, K.; Terazima, M. Excited State Intramolecular Proton Transfer Reaction of 4'- N, N -Diethylamino-3-Hydroxyflavone and Solvation Dynamics in Room Temperature Ionic Liquids Studied by Optical Kerr Gate Fluorescence Measurement J. Phys. Chem. B 2010, 114, 11847-11858
31. Suda, K.; Terazima, M.; Sato, H.; Kimura, Y. Excitation Wavelength Dependence of Excited State Intramolecular Proton Transfer Reaction of 4'- N, N -Diethylamino-3-Hydroxyflavone in Room Temperature Ionic Liquids Studied by Optical Kerr Gate Fluorescence Measurement J. Phys. Chem. B 2013, 117, 12567-12582
32. Das, R.; Klymchenko, A. S.; Duportail, G.; Mely, Y. Excited State Proton Transfer and Solvent Relaxation of a 3-Hydroxyflavone Probe in Lipid Bilayers J. Phys. Chem. B 2008, 112, 11929-11935
33. Demchenko, A. P.; Klymchenko, A. S.; Pivovarenko, V. G.; Ercelen, S.; Duportail, G.; Mely, Y. Multiparametric Color-Changing Fluorescence Probes J. Fluoresc. 2003, 13, 291-295
34. Kenfack, C. A.; Klymchenko, A. S.; Duportail, G.; Burgerc, A.; Mely, Y. Ab Initio Study of the Solvent H-Bonding Effect on ESIPT Reaction and Electronic Transitions of 3-Hydroxychromone Derivatives Phys. Chem. Chem. Phys. 2012, 14, 8910-8918
35. Smith, M. A.; Neumann, R. M.; Webb, R. A. A Modification of the Alger-Flynn-Oyamade Preparation of Flavonols J. Heterocyclic Chem. 1968, 5, 425-426
36. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A. Gaussian 09, Revision B.01; Gaussian, Inc.: Wallingford CT, 2009.
37. Tan, C. H.; Huang, Z. J.; Huang, X. G. Rapid Determination of Surfactant Critical Micelle Concentration in Aqueous Solutions Using Fiber-Optic Refractive Index Sensing Anal. Biochem. 2010, 401, 144-147
38. Warr, G. G.; Evans, D. F. Spectroscopic Determination of the Effective Dielectric Constant of Micelle-Water Interfaces between 15 and 85°C Langmuir 1988, 4, 217-224
39. Casadesús, R.; Vendrell, O.; Moreno, M.; Lluch, J. M.; Morokuma, K. On the Intramolecular Proton Transfer of 3-Hydroxyflavone in the First Singlet Excited State: A Theoretical Study Chem. Phys. 2006, 325, 243-250
40. Mennucci, B.; Tomasi, J.; Cammi, R.; Cheeseman, J. R.; Frisch, M. J.; Devlin, F. J.; Gabriel, S.; Stephens, P. J. Polarizable Continuum Model (PCM) Calculations of Solvent Effects on Optical Rotations of Chiral Molecues J. Phys. Chem. A 2002, 106, 6102-6113
41. Peng, C.; Schlegel, H. B. Combining Synchronous Transit and Quasi-Newton Methods to Find Transition States Israel J. Chem. 1993, 33, 449-454
42. Horng, M. L.; Gardecki, J. A.; Papazyan, A.; Maroncelli, M. Subpicosecond Measurements of Polar Solvation Dynamics: Coumarin 153 Revisited J. Phys. Chem. 1995, 99, 17311-17337
43. Reichardt, C. Solvatochromic Dyes as Solvent Polarity Indicators Chem. Rev. 1994, 94, 2319-2358
44. Kamlet, M. J.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W. Linear Solvation Energy Relationships. 23. A Comprehensive Collection of the Solvatochromic Parameters, π∗, α and β and Some Methods for Simplifying the Generalized Solvatochromic Equation J. Org. Chem. 1983, 48, 2877-2887
45. Abraham, M. H. Scales of Solute Hydrogen-Bonding: Their Construction and Application to Physicochemical and Biochemical Processes Chem. Soc. Rev. 1993, 22, 73-83
46. Fee, R. S.; Maroncelli, M. Estimating the Time-Zero Spectrum in Time-Resolved Emission Measurements of Solvation Dynamics Chem. Phys. 1994, 183, 235
47. Hara, K.; Kuwabara, H.; Kajimoto, O. Pressure Effect on Solvation Dynamics in Micellar Environment J. Phys. Chem. A 2001, 105, 7174-7179
48. Chakrabarty, D.; Hazra, P.; Sarkar, N. Solvation Dynamics of Coumarin 480 in TritonX-100 (TX-100) and Bile Salt Mixed Micelles J. Phys. Chem. A 2003, 107, 5887-5893
49. Shirota, H.; Segawa, H. Time-Resolved Fluorescence Study on Liquid Oligo(ethylene oxide)s: Coumarin 153 in Poly(ethylene glycol)s and Crown Ethers J. Phys. Chem. A 2003, 107, 3719-3727
50. Shirota, H.; Segawa, H. Deuterium Substitution Study on Solvation Dynamics of Liquid Poly(ethylene glycol)s Chem. Phys. 2004, 306, 43-50
51. Lin, C.-C.; Chen, C.-L.; Chung, M.-W.; Chen, Y.-J.; Chou, P.-T. Effects of Multibranching on 3-Hydroxyflavone Based Chromophores and the Excited-State Intramolecular Proton Transfer Dynamics J. Phys. Chem. A 2010, 114, 10412-10420
52. Demchenko, A. P.; Tang, K.-C.; Chou, P.-T. Excited-State Proton Coupled Charge Transfer Modulated by Molecular Structure and Media Polarization Chem. Soc. Rev. 2013, 42, 1379-1408
53. Sarkar, N.; Datta, A.; Das, S.; Bhattacharyya, K. Solvation Dynamics of Coumarin 480 in Micelles J. Phys. Chem. 1996, 100, 15483-15486