Temperature-dependent time-resolved fluorescence study of cinchonine alkaloid dication

Journal of Fluorescence

Volumn 18, Issue 1, 2008, Pages 17-27

  Mishra, Hirdyesh ^a,b   Pant, Sanjay ^b   Tripathi, Hera B ^b  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b KUMAUN UNIVERSITY   (India)

Author keywords

Cinchonine; Fluorescence quenching; Solvent relaxation

Indexed keywords

CINCHONINE; FLUORESCENCE QUENCHING; SOLVENT RELAXATION;

CHARGE TRANSFER; EXCITED STATES; FLUORESCENCE SPECTROSCOPY; RADIATION; RELAXATION PROCESSES;

POSITIVE IONS;

ANTIMALARIAL AGENT; CINCHONA ALKALOID; CINCHONINE;

ARTICLE; CHEMISTRY; ENERGY TRANSFER; FLUORESCENCE; PHOTOCHEMISTRY; SPECTROFLUOROMETRY; TEMPERATURE; TIME;

ANTIMALARIALS; CINCHONA ALKALOIDS; ENERGY TRANSFER; FLUORESCENCE; PHOTOCHEMISTRY; SPECTROMETRY, FLUORESCENCE; TEMPERATURE; TIME FACTORS;

EID: 38149140773     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-007-0229-6     Document Type: Article

References (39)

1. Franz MH, Röper S, Wartchow R, Hoffmann HMR (2004) The first and second cinchona rearrangement. Two fundamental transformations of alkaloid chemistry. J Org Chem 69:2983-2991
2. Hoffmann HMR, Frackenpohl J (2004) Recent advances in cinchona alkaloid chemistry. Eur J Org Chem 21:4293-4312
3. Kold HC, Van Nieuwenhze MS, Sharpless KB (1994) Catalytic asymmetric diydroxylation. Chem Rev 94:2463-2547
4. Braje WM, Wartchow R, Hoffmann HMR (1999) Structure and mechanism in cinchona alkaloid chemistry: overturning a 50-year-old misconception. Angew Chem Int Ed Engl 38:2539-2543
5. Yu D, Sujuki M, Xie L, Moriss-Natschke SL, Lee KH (2003) Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Med Res Rev 23:322-345
6. Hutzter JM, Walker GS, Wienkers LC (2003) Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol 16:450-459
7. Spikes JD (1998) Photosensitizing properties of quinine and synthetic antimalarials. J Photochem Photobiol B Biol 42:1-11
8. 2 (diamine)] with Cinchona alkaloid in some organic solvents. Bull Korean Chem Soc 9:355-359
9. Joshi HC, Upadhyay A, Mishra H, Tripathi HB, Pant DD (1999) Edge excitation red shift and microenvironmental effects on the photophysics of quinine bisulphate. J Photochem Photobiol A Chem 122:185-189
10. Pant S, Tripathi HB, Pant DD (1995) Solvent polarity and viscosity effect on the fluorescence spectrum and excited state decay time of quinine dication. J Photochem Photobiol A Chem 85:33-38
11. Demchenko AP (2002) The red-edge effects: 30 years of exploration. Luminescence 17:19-42
12. Pant D, Tripathi UC, Joshi GC, Tripathi HB, Pant DD (1990) Photophysics of doubly-charged quinine: steady state and time-dependent fluorescence. J Photochem Photobiol A Chem 51:313-325
13. Pant D, Tripathi HB, Pant DD (1990) Photophysics of protonated 6-methoxyquinoline: steady state and time-dependent fluorescence. J Photochem Photobiol A Chem 54:239-249
14. Itoh K, Azumi T (1975) Shift of the emission band upon excitation at the long wavelength absorption edge. II. Importance of the solute-solvent interaction and the solvent reorientation relaxation process. J Chem Phys 62:3431-3438
15. O'Connor DV, Meech SR, Phillips D (1982) Complex fluorescence decay of quinine bisulphate in aqueous sulphuric acid solution. Chem Phys Lett 88:22-26
16. Bakhshiev NG (1962) Universal molecular interactions and their effect on the position of the electronic spectra of molecules in two component solutions. II. Phthalimide derivatives (liquid solutions). Opt Spektrosk 12:582-587
17. Bakhshiev NG (1962) Universal intermolecular interactions and their effect on the position of electron spectra of molecules in dissolved two-component solutions. VI. Dipole moments and the structure of molecules of some derivatives of phthalimide in the ground and the first excited electron states. Opt Spektrosk 13:192-201
18. Bakhshiev NG, Mazurenko YT, Peterskaya IV (1966) Luminescence decay in various regions of the luminescence spectrum of molecules in viscous solvents. Opt Spektrosk 21(5):550-554
19. Bakhshiev NG, Klochkov VP, Neporent BS, Cherkasov AS (1962) Absorption and fluorescence of the vapor of anthracene and its derivatives. Opt Spektrosk 12:582-587
20. Bakhshiev NG, Gularyan SK, Dobretsov GE, Kirillova YA, Svetlichny VY (2006) Solvatochromism and solvatofluorochromism of the intramolecular charge transfer and of 4-dimethylaminochalcone in the electronic spectra of its solutions. Opt Spectrosc 100:700-708
21. Azumi T, Itoh K, Shiraishi H (1976) Shift of emission band upon the excitation at the long wavelength absorption edge. III. Temperature dependence of the shift and correlation with the time dependent spectral shift. J Chem Phys 65:2550-2555
22. Ikeyama T, Azumi T, Murso T, Yamazaki I (1983) Shift of emission band upon excitation at the long-wavelength absorption edge. Time-dependent fluorescence shift of a fluid ethanol solution of 6-methoxyquinoline. Chem Phys Lett 96:419-421
23. Meech SR, Phillips D (1983) Photophysics of some common fluorescence standards. J Photochem 23:193-217
24. Mishra H (2002) Photoinduced electronic excited state relaxation and proton transfer phenomena in some hydrogen bonded molecules. Ph.D. Thesis, Kumaon University, Nainital, India
25. Pant S, Pant D, Tripathi HB (1993) Photophysics of the dications of cinchonine and cinchonidine. J Photochem Photobiol A Chem 75:137-149
26. Liu Y, Yang YW, Zhang HY, Hu BW, Ding F, Li CJ (2004) Diastereoisomer selective inclusion of Cinchona alkaloids with a modified β-cyclodextrin: fluorescent behaviour enhance by chiral teather binding. Short communication. Chem Biodivers 1:481-488
27. Mishra H, Pant D, Pant TC, Tripathi HB (2006) Edge excitation red shift and energy migration in quinine bisulphate dication. J Photochem Photobiol A Chem 177:197-204
28. Strickler S, Berg RA (1962) Relationship between absorption intensity and fluorescence decay time of molecules. J Chem Phys 37:814
29. Kosower EM, Dodiuk H, Kanety H (1978) Intramolecular donor-acceptor system. 4. Solvent effects on radiative and nonradiative processes for the charge-transfer states of N-arylaminonaphthalenesulfonates. J Am Chem Soc 100:4179-4188
30. Ghiggino KP, Lee AG, Meech SR, O'Connor DV, Phillips D (1981) Time-resolved emission spectroscopy of the dansyl fluorescence probe. Biochemistry 20:5381-5389
31. Bismuto E, Jameson DM, Gratton E (1987) Dipolar relaxations in glycerol: a dynamic fluorescence study of 4-[2′-(dimethylamino)-6′-naphthoyl] cyclohexanecarboxylic acid (DANCA). J Am Chem Soc 109:2354-2357
32. Sun JS, Rougee M, Delarue M, Garestier TM, Helene C (1990) Solvent relaxation around excited 2-methoxy-6-chloro-9-aminoacridine in aqueous solvents. J Phys Chem 94:968-977
33. DeToma RP, Ester JH, Brand L (1976) Dynamic interaction of fluorescence probes with the solvent environment. J Am Chem Soc 98:5001-5007
34. Jimenez R, Fleming GR, Kumar PV, Maroncelli M (1994) Femtosecond solvation dynamics of water. Femtosecond solvation dynamics of water. Nature 369:471-473
35. Impey W, Madden PA, Mcdonald IR (1983) Hydration and mobility of ions in solution. J Phys Chem 87:5071-5083
36. Guardia E, Padro JA (1990) Molecular dynamics simulation of single ions in aqueous solutions: effects of the flexibility of the water molecules. J Phys Chem 94:6049-6055
37. Wang Y, Tominaga Y (1994) Dynamical structure of water in aqueous electrolyte solutions by low-frequency Raman scattering. J Chem Phys 101:3453-3458
38. Obst S, Bradaczek H (1996) Molecular dynamics study of the structure and dynamics of the hydration shell of alkaline and alkaline-earth metal cations. J Phys Chem 100:15677-15687
39. 2+ in water studied by Born-Oppenheimer ab initio QM/MM dynamics. J Phys Chem A 101:6299-6309