Acid-base behavior of 3-aminoquinoline in its ground and excited states

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 207, Issue 2-3, 2009, Pages 254-259

  Panda, Debashis ^a   Ghosh, Debanjana ^a   Datta, Anindya ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Fluorescence; Nafion; Photophysics; pKb

Indexed keywords

EID: 70249097290     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2009.07.017     Document Type: Article

References (28)

1. Farruggia G., Iotti S., Prodi L., Montalti M., Zaccheroni N., Savage P.B., Trapani V., Sale P., and Wolf F.I. 8-Hydroxyquinoline derivatives as fluorescent sensors for magnesium in living cells. J. Am. Chem. Soc. 128 (2006) 344-350
2. Jayaraman S., and Verkman A.S. Quenching mechanism of quinolinium-type chloride-sensitive fluorescent indicators. Biophys. Chem. 85 (2000) 49-57
3. Solntsev K.M., Clower C.E., Tolbert L.M., and Huppert D. 6-Hydroxyquinoline-N-oxides: a new class of "super" photoacids. J. Am. Chem. Soc. 127 (2005) 8534-8544
4. Kwon O.-H., Lee Y.-S., Yoo B.K., and Jang D.-J. Excited-state triple proton transfer of 7-hydroxyquinoline along a hydrogen-bonded alcohol chain: vibrationally assisted proton tunneling. Angew. Chem. Int. Ed. 45 (2006) 415-419
5. Panda D., and Datta A. The role of the ring nitrogen and the amino group in the solvent dependence of the excited-state dynamics of 3-aminoquinoline. J. Chem. Phys. 125 (2006) 054513/1-054513/9
6. Lee P.C., and Meisel D. Luminescence quenching in the cluster network of perfluorosulfonate membrane. J. Am. Chem. Soc. 102 (1980) 5477-5481
7. Szentirmay M.N., and Martin C.R. Ion-exchange selectivity of nafion films on electrode surfaces. Anal. Chem. 56 (1984) 1898-1902
8. Mukherjee T.K., and Datta A. Regulation of the extent and dynamics of excited-state proton transfer in 2-(2′-pyridyl)benzimidazole in nafion membranes by cation exchange. J. Phys. Chem. B 110 (2006) 2611-2617
9. Moilanen D.E., Piletic I.R., and Fayer M.D. Tracking water's response to structural changes in nafion membranes. J. Phys. Chem. A 110 (2006) 9084-9088
10. Dixon J.M., Taniguchi M., and Lindsey J.S. PhotochemCAD 2: a refined program with accompanying spectral databases for photochemical calculations. Photochem. Photobiol. 81 (2005) 212-213
11. Panda D., Khatua S., and Datta A. Enhanced fluorescence of epicocconone in surfactant assemblies as a consequence of depth-dependent microviscosity. J. Phys. Chem. B 111 (2007) 1648-1656
12. Becke A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98 (1993) 5648-5652
13. Becke A.D. A new mixing of Hartree-Fock and local-density-functional theories. J. Chem. Phys. 98 (1993) 1372-1377
14. Frisch M.J., et al. Gaussian 03, Revision C. 02 (2004), Gaussian, Inc., Wallingford, CT
15. Mennucci B., Cances E., and Tomasi J. Evaluation of solvent effects in isotropic and anisotropic dielectrics and in ionic solutions with a unified integral equation method: theoretical bases, computational implementation, and numerical applications. J. Phys. Chem. B 101 (1997) 10506-10517
16. a calculations for carboxylic acids using complete basis set and Gaussian-n models combined with CPCM continuum solvation methods. J. Am. Chem. Soc. 123 (2001) 7314-7319
17. a calculations with continuum dielectric methods. J. Phys. Chem. 95 (1991) 5610-5620
18. a calculations of aliphatic amines, diamines, and aminoamides via density functional theory with a Poisson-Boltzmann continuum solvent model. J. Phys. Chem. 111 (2007) 4422-4430
19. Wehry E.L. Modern Fluorescence Spectroscopy (1976), Plenum Press, New York/London
20. 13C NMR spectra, and AM1 studies of protonation of aminopyridines. J. Mol. Struct. 322 (1994) 223-232
21. Smith B.J. Calculation of aqueous proton dissociation constants of quinoline and hydroxyquinolines: a comparison of solvation models. Phys. Chem. Chem. Phys. 2 (2000) 5383-5388
22. Pouët M.-F., Baures E., Vaillant S., and Thomas O. Hidden isosbestic point(s) in ultraviolet spectra. Appl. Spectrosc. 58 (2004) 486-490
23. Panda D., and Datta A. Implications of area normalization of multi-component spectra. Appl. Spectrosc. 62 (2008) 341-344
24. Tissandier M.D., Cowen K.A., Feng W.Y., Gundlach E., Cohen M., Earhart A.D., and Coe J.V. The proton's absolute aqueous enthalpy and Gibbs free energy of solvation from cluster-ion solvation data. J. Phys. Chem. A 102 (1998) 7787-7794
25. +". J. Phys. Chem. A 109 (2005) 10795-10797
26. Pliego J.R., and Riveros J.M. Gibbs energy of solvation of organic ions in aqueous and dimethyl sulfoxide solutions. Phys. Chem. Chem. Phys. 4 (2002) 1622-1627
27. +. J. Phys. Chem. A 108 (2004) 3692-3694
28. a values of guanine in water: density functional theory calculations combined with Poisson-Boltzmann continuum-solvation model. J. Phys. Chem. B 107 (2003) 344-357