Singlet excited state pyridinic deprotonation of the N 9- methylbetacarboline cations in aqueous sodium hydroxide solutions

Journal of Fluorescence

Volumn 20, Issue 1, 2010, Pages 163-170

  Sánchez Coronilla, Antonio ^a   Carmona, Carmen ^a   Muñoz, María A ^a   Balón, Manuel ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

Betacarboline; Deprotonation; Excited state; Proton transfer

Indexed keywords

BETACARBOLINE; EXCIPLEXES; EXCITED STATE LIFETIMES; EXCITED STATE REACTIONS; NAOH SOLUTIONS; PH RANGE; SINGLET EXCITED STATE; SODIUM HYDROXIDE SOLUTIONS; STEADY STATE; TIME-RESOLVED FLUORESCENCE MEASUREMENTS; WATER MOLECULE;

COOLING SYSTEMS; DEPROTONATION; PH EFFECTS; PLATINUM COMPOUNDS; POSITIVE IONS; POSITIVE TEMPERATURE COEFFICIENT; PROTONS;

EXCITED STATES;

9 METHYL BETA CARBOLINE; 9-METHYL-BETA-CARBOLINE; CARBOLINE DERIVATIVE; FORMAMIDE DERIVATIVE; N,N DIMETHYLFORMAMIDE; N,N-DIMETHYLFORMAMIDE; PROTON; PYRIDINE DERIVATIVE; SODIUM HYDROXIDE; WATER;

ABSORPTION; ARTICLE; CHEMISTRY; SOLUTION AND SOLUBILITY; SPECTROFLUOROMETRY;

ABSORPTION; CARBOLINES; FORMAMIDES; PROTONS; PYRIDINES; SODIUM HYDROXIDE; SOLUTIONS; SPECTROMETRY, FLUORESCENCE; WATER;

EID: 77951022248     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-009-0534-3     Document Type: Article

References (27)

1. JF Ireland PAH Wyatt 1976 Acid-base properties of electronically excited states of organic molecules Phys Org Chem 12 131 221 1:CAS:528: DyaE28XktVClt7Y%3D
2. Kelly RN, Schulman G (1998) Proton transfer kinetics of electronically excited acids and bases, in molecular luminescence spectroscopy. Methods and applications: Part 2, Chap 6. Wiley, pp 461-511
3. L Arnaut S Formosinho 1993 Excited-state proton-transfer reactions. I Fundamentals and intermolecular reactions J Photochem Photobiol A: Chem 75 1 20 10.1016/1010-6030(93)80157-5 1:CAS:528:DyaK2cXhs1aqtrs%3D
4. Waluk J (2000) Conformational aspects of intra- and intermolecular excited-state proton transfer, in Conformational Analysis of Molecules in Excited States, Chap 2. Wiley-VCH, pp 57-111
5. D Marx 2006 Proton transfer 200 years after von Grotthus: insights from ab initio simulations Chem Phys Chem 7 9 1848 1870 1:CAS:528:DC%2BD28XhtVWgtL7L 16929553
6. N Agmon 2005 Elementary steps in excited-state proton transfer J Phys Chem A 109 1 13 35 10.1021/jp047465m 1:CAS:528:DC%2BD2cXhtVyltrnE 16839085 (Pubitemid 40121017)
7. OF Mohammed D Pines J Dreyer E Pines ETJ Nibbering 2005 Sequential proton transfer through water bridges in acid-base reactions Science 310 83 86 10.1126/science.1117756 1:CAS:528:DC%2BD2MXhtVOjsr7M 16210532 (Pubitemid 41434539)
8. BJ Siwick HJ Bakker 2007 On the role of water in intermolecular proton-transfer reactions J Am Chem Soc 129 44 13412 13420 10.1021/ja069265p 1:CAS:528:DC%2BD2sXhtFKhtbvL 17935322 (Pubitemid 350071769)
9. RA Abramovitch ID Spencer 1964 The carbolines Adv Heterocycl Chem 3 1 79 207 10.1016/S0065-2725(08)60542-5 1:CAS:528:DyaF2MXmsFyqtQ%3D%3D 5332970
10. JRF Allen BR Holmstedt 1980 The simple 3-carboline alkaloids Phytochem 19 1573 1982 10.1016/S0031-9422(00)83773-5 1:CAS:528:DyaL3MXhvFKi
11. M Balón MA Muñoz P Guardado J Hidalgo C Carmona 1994 Photophysics and photochemistry of betacarbolines Trends Photochem and Photobiol 3 1 117 138
12. M Balón J Hidalgo P Guardado MA Muñoz C Carmona 1993 Acid-base and spectral properties of betacarbolines. Part 2. dehydro and fully aromatic betacarbolimes J Chem Soc Perkin Trans 2 99 104
13. M Balón C Carmona P Guardado MA Muñoz 1998 Hydrogen-bonding and proton transfer interactions between Harmane and trifluoroethanol in the ground and excited singlet states Photochem Photobiol 67 4 414 419 10.1111/j.1751-1097.1998.tb05220.x (Pubitemid 128472695)
14. C Carmona M Galán G Angulo MA Muñoz P Guardado M Balón 2000 Ground and singlet excited states hydrogen bonding interactions of betacarbolines Phys Chem Chem Phys 2 22 5076 5083 10.1039/b005455k 1:CAS:528:DC%2BD3cXnvVyntrk%3D
15. 9-methyl harmane J Phys Chem A 105 45 10334 10338 10.1021/jp0104942 1:CAS:528:DC%2BD3MXns12lsLo%3D (Pubitemid 35378467)
16. C Carmona M Balón M Galán P Guardado MA Muñoz 2002 Dynamic study of excited state hydrogen-bonded complexes of harmane in cyclohexane-toluene mixtures Photochem Photobiol 76 3 239 246 10.1562/0031-8655(2002)076<0239:DSOESH>2.0.CO;2 1:CAS:528: DC%2BD38XnsFGrtbY%3D 12403443
17. C Carmona M Balón A Sánchez Coronilla MA Muñoz 2004 New insights on the excited-state proton-transfer reactions of betacarbolines: cationic exciplex formation J Phys Chem A 108 1910 1918 10.1021/jp030829a 1:CAS:528:DC%2BD2cXhsVWktLc%3D
18. 9- methylbetacarboline in water-N,N-dimethylformamide mixtures J Fluoresc 10.1007/s10895-0502-y
19. R Sakuros KP Ghiggino 1982 Excited state proton transfer in betacarboline J Photochem 18 1 1 8 10.1016/0047-2670(82)80002-6
20. OV Wolfbeis E Fürlinger R Wintersteiger 1982 Solvent and pH-dependence of the absorption and fluorescence spectra of Harman: detection of three ground state and four excited state species Monatsh Chem 113 509 517 10.1007/BF00799926 1:CAS:528:DyaL38XksFKisr4%3D
21. S Draxler ME Lippitsch 1993 Excited-state acid-base kinetics and equilibria in norharman J Phys Chem 99 44 11493 11496 10.1021/j100146a024
22. A Dias AP Varela MG Miguel RS Becker HD Burrows AL Maçanita 1996 β-Carbolines. 2. Rate constants of proton transfer from multiexponential decays on the lowest singlet excited state of harmine in water as a function of pH J Phys Chem 100 45 17970 17977 10.1021/jp961406u 1:CAS:528:DyaK28Xmt1Ggur8%3D (Pubitemid 126790078)
23. A Dias AP Varela MG Miguel AL Maçanita RS Becker 1992 β-Carboline Photosensitizers. 1. Photophysics, kinetics and excited-state equilibria in organic solvents, and theoretical calculations J Phys Chem 96 25 10290 10296 10.1021/j100204a036 1:CAS:528:DyaK38XmsVamtL4%3D
24. A Sánchez-Coronilla C Carmona MA Muñoz M Balón 2006 Ground state isomerism and dual emission of the β-carboline anhydrobase (N2-methyl-)H-pyrido[3, 4-b]indole) in aprotic solvents Chem Phys 327 1 70 76 10.1016/j.chemphys.2006.03.032
25. A Sánchez-Coronilla M Balon MA Muñoz C Carmona 2008 Influence of hydrogen bonding in the ground and the excited states of the isomers of the β-carboline anhydrobase (N2-methyl-9H-pyrido[3. 4-b]indole) in aprotic solvents Chem Phys 344 1 72 78 10.1016/j.chemphys.2007.11.011
26. A Sánchez-Coronilla M Balon MA Muñoz J Hidalgo C Carmona 2008 Ground state isomerism in betacarboline hydrogen bond complexes: the charge transfer nature of its large Stokes shifted emission Chem Phys 351 1 27 32 10.1016/j.chemphys.2008.03.025
27. Lakowicz JR (1999) Principles of fluorescence spectroscopy, Second Edition, Chapter 4. Kluwer Academic/Plenum Publishers, New York, pp 95-140