Artículo

Cabanzo Hernández, R.; David Gara, P.M.; Velasco, D.M.; Erra-Balsells, R.; Bilmes, G.M. "Photophysical behavior of new acridine(1,8)dione dyes" (2013) Photochemical and Photobiological Sciences. 12(11):1968-1975
El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

The photophysical behavior of five acridine(1,8)dione dyes of biological interest was studied by absorption and fluorescence spectroscopy, photoacoustics and time resolved phosphorescence techniques. The results obtained in ethanol and acetonitrile solutions show that the main spectroscopic and photophysical parameters of these compounds depend strongly on both the solvent and oxygen concentrations. Oxygen completely quenched the triplet state of all dyes. In nitrogen-saturated solutions, quantum efficiencies of triplet formation in ethanol were lower than those in acetonitrile. © The Royal Society of Chemistry and Owner Societies.

Registro:

Documento: Artículo
Título:Photophysical behavior of new acridine(1,8)dione dyes
Autor:Cabanzo Hernández, R.; David Gara, P.M.; Velasco, D.M.; Erra-Balsells, R.; Bilmes, G.M.
Filiación:Laboratorio de Espectroscopia Atómica y Molecular, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia
Centro de Investigaciones Ópticas-CIOp (CONICET-CIC), Universidad Nacional de la Plata, Casilla de Correo 124, (1900) La Plata, Argentina
Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia
CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón II, (1428) Buenos Aires, Argentina
Año:2013
Volumen:12
Número:11
Página de inicio:1968
Página de fin:1975
DOI: http://dx.doi.org/10.1039/c3pp50159k
Título revista:Photochemical and Photobiological Sciences
Título revista abreviado:Photochem. Photobiol. Sci.
ISSN:1474905X
CODEN:PPSHC
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v12_n11_p1968_CabanzoHernandez

Referencias:

  • Maidwell, N.L., Reza Rezai, M., Roeschlaub, C.A., Sammes, P.G., On the development of NAD(P)H-sensitive fluorescent probes (2000) J. Chem. Soc., Perkin Trans. 1, pp. 1541-1546
  • Mohan, H., Mittal, J.P., Venkatachalapathy, B., Srividya, N., Ramamurthy, P., Reaction of OH, OOH, O- and specific one-electron oxidants with 3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-(1,8) (2H,5H)-acridinedione. Ground- and excited-state and transient acid-base properties (1997) J. Chem. Soc., Faraday Trans., 93, pp. 4269-4274
  • Gopalakrishnan, M., Miller, T.R., Buckner, S.A., Milidc, I., Molinari, E.J., Whiteaker, K.L., Davis-Taher, R., Carroll, W.A., Pharmacological characterization of a 1,4-dihydropyridine analogue, 9-(3,4-dichlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H) -acridinedione (A-184209) as a novel K<inf>ATP</inf> channel inhibitor (2003) Br. J. Pharmacol., 138, pp. 393-399
  • Jeyakanthan, J., Shanmuga Sundara Raj, S., Velmurugan, D., Fun, H.-K., Rajan, T.J., Ramakrishnan, V.T., Two benzoylaminoacridinedione derivatives (2000) Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 56, pp. 1109-1112
  • Karolac-Wojciechowska, J., Mrozek, A., Amiel, P., Brouant, P., Barbe, J., A Potential Antiprotozoal Drug Containing Acridine and Thiadiazole Moieties (1996) Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 52, pp. 2939-2941
  • Sankaranarayanan, R., Shanmuga Sundara Raj, S., Velmurugan, D., Fun, H.-K., 1,2,3,4,5,6,7,8-Octahydro-3,3,6,6-tetramethylacridine-1,8-dione (1999) Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 55, pp. 1513-1514
  • Sankaranarayanan, R., Velmurugan, D., Murugan, P., Ramasubbu, N., 1,2,3,4,5,6,7,8,9,10-Decahydro-3,3,6,6-tetramethyl-1,8-dioxo-10- vinylacridin-9-ylmethyl acetate (1998) Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 54, pp. 1534-1535
  • Ganesh, V.K., Velmurugan, D., Bidya Sagar, M., Murugan, P., 9-(4-Dimethylaminophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1, 8(2H,5H)-acridinedione (1998) Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 54, pp. 557-559
  • Ganesh, V.K., Banumathi, S., Velmurugan, D., Ramasubbu, N., Ramakrishnan, V.T., 9-(4-Methoxyphenyl)-10-phenyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H) -acridinedione (1998) Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 54, pp. 633-635
  • Aravindan, P.G., Yogavel, M., Velmurugan, D., Murugan, P., Shanmuga Sundara Raj, S., Fun, H.-K., 3,3,6,6-Tetramethyl-9-(4-pyridyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H) -acridinedione monohydrate (2003) Acta Crystallogr., Sect. E: Struct. Rep. Online., 59, pp. 659-661
  • Timpe, H.J., Ulrich, S., Decker, C., Fouassier, J.P., Photoinitiated polymerization of acrylates and methacrylates with decahydroacridine-1,8-dione/onium salt initiator systems (1993) Macromolecules, 26, pp. 4560-4566
  • Ulrich, S., Timpe, H.J., Fouassier, J.P., Photochemistry and use of decahydroacridine-1,8-diones as photosensitizers for onium salt decomposition (1993) J. Photochem. Photobiol., A, 73, pp. 139-150
  • Karunakaran, V., Ramamurthy, P., Josephrajan, T., Ramakrishnan, V.T., Solvent effects and photophysical studies of a new class of acridine(1,8)dione dyes (2002) Spectrochim Acta, Part A, 58, pp. 1443-1451
  • Srividya, N., Ramamurthy, P., Ramakrishnan, V.T., Photophysical studies of acridine(1,8)dione dyes: A new class of laser dyes (1998) Spectrochim Acta, Part A, 54, pp. 245-253
  • Srividya, N., Ramamurthy, P., Ramakrishnan, V.T., Solvent effects on the absorption and fluorescence spectra of some acridinedione dyes: Determination of ground and excited state dipole moments (1997) Spectrochim Acta, Part A, 53, pp. 1743-1753
  • Lakowicz, J.R., (2006) Principles of Fluorescence Spectroscopy, , Springer-Verlag, New York
  • Wilkinson, F., McGarvey, D.J., Olea, A.F., Factors governing the efficiency of singlet oxygen production during oxygen quenching of singlet and triplet states of anthracene derivatives in cyclohexane solution (1993) J. Am. Chem. Soc., 115, pp. 12144-12151
  • Gensch, T., Viappiani, C., Time-resolved photothermal methods: Accessing time-resolved thermodynamics of photoinduced processes in chemistry and biology (2003) Photochem. Photobiol. Sci., 2, pp. 699-721
  • Biondic, M.C., Erra-Balsells, R., Photochemical reaction of harmaline. Part 1. Electronic spectra (1992) J. Chem. Soc., Perkin Trans. 2, pp. 1049-1058
  • Rodgers, M.A.J., Snowden, P.T., Lifetime of oxygen (O2(1.DELTA.G)) in liquid water as determined by time-resolved infrared luminescence measurement (1982) J. Am. Chem. Soc., 104, pp. 5541-5543
  • Scurlock, R.D., Nonell, S., Braslavsky, S.E., Ogilby, P.R., Effect of solvent on the radiative decay of singlet molecular oxygen (a1.DELTA.G) (1995) J. Phys. Chem., 99, pp. 3521-3526
  • Stracke, F., Heupel, M., Thiel, E., Singlet molecular oxygen photosensitized by rhodamine dyes: Correlation with photophysical properties of the sensitizers (1999) J. Photochem. Photobiol., A, 126, pp. 51-58
  • Martí, C., Jürgens, O., Cuenca, O., Casals, M., Nonell, S., Aromatic ketones as standards for singlet molecular oxygen O2( 1Δ<inf>g</inf>) photosensitization. Time-resolved photoacoustic and near-IR emission studies (1996) J. Photochem. Photobiol., A, 97, pp. 11-18
  • Braslavsky, S.E., Heibel, G.E., Time-resolved photothermal and photoacoustic methods applied to photoinduced processes in solution (1992) Chem. Rev., 92, pp. 1381-1410
  • Rothberg, L.J., Simon, J.D., Bernstein, M., Peters, K.S., Pulsed laser photoacoustic calorimetry of metastable species (1983) J. Am. Chem. Soc., 105, pp. 3464-3468
  • Rudzki Small, J., Libertini, L.J., Small, E.W., Analysis of photoacoustic waveforms using the nonlinear least squares method (1992) Biophys. Chem., 42, pp. 29-48
  • Mesaros, M., Tarzi, O.I., Erra-Balsells, R., Bilmes, G.M., The photophysics of some UV-MALDI matrices studied by using spectroscopic, photoacoustic and luminescence techniques (2006) Chem. Phys. Lett., 426, pp. 334-340
  • Srividya, N., Ramamurthy, P., Ramakrishnan, V.T., Photooxidation of acridine(1,8)dione dyes: Flash photolysis investigation of the mechanistic details (2000) Phys. Chem. Chem. Phys., 2, pp. 5120-5126
  • Venkatachalapathy, B., Ramamurthy, P., Excited state proton and electron transfer reactions of acridinedione dyes with amines (1999) Phys. Chem. Chem. Phys., 1, pp. 2223-2230
  • Mohan, H., Srividya, N., Ramamurthy, P., Mittal, J.P., Kinetics and spectral characteristics of transient species formed on one-electron oxidation of acridine-1,8-dione in aqueous solution pulse radiolysis study (1996) J. Chem. Soc., Faraday Trans., 92, pp. 2353-2359
  • Mohan, H., Mittal, J.P., Electron-transfer and excited-state properties of radiolytically generated transients of acridine(1,8)dione dyes in an organic matrix (2001) J. Photochem. Photobiol., A, 141, pp. 25-32
  • Li, Q., Batchelor-Mcauley, C., Lawrence, N.S., Hartshorne, R.S., Compton, R.G., Anomalous solubility of oxygen in acetonitrile/water mixture containing tetra-n-butylammonium perchlorate supporting electrolyte; The solubility and diffusion coefficient of oxygen in anhydrous acetonitrile and aqueous mixtures (2013) J. Electroanal. Chem., 688, pp. 328-355
  • Srividya, N., Ramamurthy, P., Shanmugasundaram, P., Ramakrishnan, V.T., Synthesis, characterization, and electrochemistry of some acridine-1,8-dione dyes (1996) J. Org. Chem., 61, pp. 5083-5089
  • Murugan, P., Shanmugasundaram, P., Ramakrishnan, V.T., Venkatachalapathy, B., Srividya, N., Ramamurthy, P., Gunasekaran, K., Velmurugan, D., Synthesis and laser properties of 9-alkyl-3,3,6,6-tetramethyl-1,2,3,4,5, 6,7,8,9,10-decahydroacridine-1,8-dione derivatives (1998) J. Chem. Soc. Perkin Trans. 2., pp. 999-1004
  • Miller, J.N., (1981) Standards in Fluorescence Spectrometry, , Chapman & Hall, London
  • Schmidt, R., Tanielian, C., Dunsbach, R., Wolff, C., Phenalenone, a universal reference compound for the determination of quantum yields of singlet oxygen O<inf>2</inf>(1Δ<inf>g</inf>) sensitization (1994) J. Photochem. Photobiol., A, 79, pp. 11-17
  • Mesaros, M., Bonesi, S.M., Ponce, M.A., Erra-Balsellsv, R., Bilmes, G.M., The photophysics of nitrocarbazoles studied by using spectroscopic, photoacoustic and luminescence techniques (2003) Photochem. Photobiol. Sci., 2, pp. 808-816
  • Van Haver, P., Viaene, L., Van Der Auweraes, M., De Schryver, F.C., References for laser-induced opto-acoustic spectroscopy using UV excitation (1990) J. Photochem. Photobiol., A, 63, pp. 265-277

Citas:

---------- APA ----------
Cabanzo Hernández, R., David Gara, P.M., Velasco, D.M., Erra-Balsells, R. & Bilmes, G.M. (2013) . Photophysical behavior of new acridine(1,8)dione dyes. Photochemical and Photobiological Sciences, 12(11), 1968-1975.
http://dx.doi.org/10.1039/c3pp50159k
---------- CHICAGO ----------
Cabanzo Hernández, R., David Gara, P.M., Velasco, D.M., Erra-Balsells, R., Bilmes, G.M. "Photophysical behavior of new acridine(1,8)dione dyes" . Photochemical and Photobiological Sciences 12, no. 11 (2013) : 1968-1975.
http://dx.doi.org/10.1039/c3pp50159k
---------- MLA ----------
Cabanzo Hernández, R., David Gara, P.M., Velasco, D.M., Erra-Balsells, R., Bilmes, G.M. "Photophysical behavior of new acridine(1,8)dione dyes" . Photochemical and Photobiological Sciences, vol. 12, no. 11, 2013, pp. 1968-1975.
http://dx.doi.org/10.1039/c3pp50159k
---------- VANCOUVER ----------
Cabanzo Hernández, R., David Gara, P.M., Velasco, D.M., Erra-Balsells, R., Bilmes, G.M. Photophysical behavior of new acridine(1,8)dione dyes. Photochem. Photobiol. Sci. 2013;12(11):1968-1975.
http://dx.doi.org/10.1039/c3pp50159k