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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.

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References

  1. N. L. Maidwell, M. Reza Rezai, C. A. Roeschlaub, P. G. Sammes, On the development of NAD(P)H-sensitive fluorescent probes, J. Chem. Soc., Perkin Trans. 1, 2000, 1541–1546.

    Google Scholar 

  2. H. Mohan, J. P. Mittal, B. Venkatachalapathy, N. Srividya, P. Ramamurthy, Reaction of ˙H, ˙OH, 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, J. Chem. Soc., Faraday Trans., 1997, 93, 4269–4274.

    Article  CAS  Google Scholar 

  3. M. Gopalakrishnan, T. R. Miller, S. A. Buckner, I. Milidc, E. J. Molinari, K. L. Whiteaker, R. Davis-Taher, V. E. Scott, C. Cassidy, J. P. Sullivan, W. A. Carroll, 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 KATP channel inhibitor, Br. J. Pharmacol., 2003, 138, 393–399.

    Article  CAS  Google Scholar 

  4. J. Jeyakanthan, S. Shanmuga Sundara Raj, D. Velmurugan, H.-K. Fun, T. J. Rajan, V. T. Ramakrishnan, Two benzoylaminoacridinedione derivatives, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 2000, 56, 1109–1112.

    Article  Google Scholar 

  5. J. Karolac-Wojciechowska, A. Mrozek, P. Amiel, P. Brouant, J. Barbe, A Potential Antiprotozoal Drug Containing Acridine and Thiadiazole Moieties, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1996, 52, 2939–2941.

    Article  Google Scholar 

  6. R. Sankaranarayanan, S. Shanmuga Sundara Raj, D. Velmurugan, H.-K. Fun, 1,2,3,4,5,6,7,8-Octahydro-3,3,6,6-tetramethylacridine-1,8-dione, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1999, 55, 1513–1514.

    Article  Google Scholar 

  7. R. Sankaranarayanan, D. Velmurugan, P. Murugan, N. Ramasubbu, 1,2,3,4,5,6,7,8,9,10-Decahydro-3,3,6,6-tetramethyl-1,8-dioxo-10-vinylacridin-9-ylmethyl acetate, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1998, 54, 1534–1535.

    Article  Google Scholar 

  8. V. K. Ganesh, D. Velmurugan, M. Bidya Sagar, P. Murugan, 9-(4-Dimethylaminophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1998, 54, 557–559.

    Article  Google Scholar 

  9. V. K. Ganesh, S. Banumathi, D. Velmurugan, N. Ramasubbu, V. T. Ramakrishnan, 9-(4-Methoxyphenyl)-10-phenyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1998, 54, 633–635.

    Article  Google Scholar 

  10. P. G. Aravindan, M. Yogavel, D. Velmurugan, P. Murugan, S. Shanmuga Sundara Raj, H.-K. Fun, 3,3,6,6-Tetramethyl-9-(4-pyridyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione monohydrate, Acta Crystallogr., Sect. E: Struct. Rep. Online., 2003, 59, 659–661.

    Article  Google Scholar 

  11. H. J. Timpe, S. Ulrich, C. Decker, J. P. Fouassier, Photoinitiated polymerization of acrylates and methacrylates with decahydroacridine-1,8-dione/onium salt initiator systems, Macromolecules, 1993, 26, 4560–4566.

    Article  CAS  Google Scholar 

  12. S. Ulrich, H. J. Timpe, J. P. Fouassier, Photochemistry and use of decahydroacridine-1,8-diones as photosensitizers for onium salt decomposition, J. Photochem. Photobiol., A, 1993, 73, 139–150.

    Article  Google Scholar 

  13. V. Karunakaran, P. Ramamurthy, T. Josephrajan, V. T. Ramakrishnan, Solvent effects and photophysical studies of a new class of acridine(1,8)dione dyes, Spectrochim Acta, Part A, 2002, 58, 1443–1451.

    Article  CAS  Google Scholar 

  14. N. Srividya, P. Ramamurthy, V. T. Ramakrishnan, Photophysical studies of acridine(1,8)dione dyes: a new class of laser dyes, Spectrochim Acta, Part A, 1998, 54, 245–253.

    Article  Google Scholar 

  15. N. Srividya, P. Ramamurthy, V. T. Ramakrishnan, Solvent effects on the absorption and fluorescence spectra of some acridinedione dyes: determination of ground and excited state dipole moments, Spectrochim Acta, Part A, 1997, 53, 1743–1753.

    Article  Google Scholar 

  16. J. R. Lakowicz, Principles of fluorescence spectroscopy, Springer-Verlag, New York, 2006.

    Book  Google Scholar 

  17. F. Wilkinson, D. J. McGarvey, A. F. Olea, Factors governing the efficiency of singlet oxygen production during oxygen quenching of singlet and triplet states of anthracene derivatives in cyclohexane solution, J. Am. Chem. Soc., 1993, 115, 12144–12151.

    Article  CAS  Google Scholar 

  18. T. Gensch, C. Viappiani, Time-resolved photothermal methods: accessing time-resolved thermodynamics of photoinduced processes in chemistry and biology, Photochem. Photobiol. Sci., 2003, 2, 699–721.

    Article  CAS  Google Scholar 

  19. M. C. Biondic, R. Erra-Balsells, Photochemical reaction of harmaline. Part 1. Electronic spectra, J. Chem. Soc., Perkin Trans. 2, 1992, 1049–1058.

    Google Scholar 

  20. M. A. J. Rodgers, P. T. Snowden, Lifetime of oxygen (O2(1.DELTA.g)) in liquid water as determined by time-resolved infrared luminescence measurement, J. Am. Chem. Soc., 1982, 104, 5541–5543.

    Article  CAS  Google Scholar 

  21. R. D. Scurlock, S. Nonell, S. E. Braslavsky, P. R. Ogilby, Effect of solvent on the radiative decay of singlet molecular oxygen (a1.DELTA.g), J. Phys. Chem., 1995, 99, 3521–3526.

    Article  CAS  Google Scholar 

  22. F. Stracke, M. Heupel, E. Thiel, Singlet molecular oxygen photosensitized by rhodamine dyes: correlation with photophysical properties of the sensitizers, J. Photochem. Photobiol., A, 1999, 126, 51–58.

    Article  CAS  Google Scholar 

  23. C. Martí, O. Jürgens, O. Cuenca, M. Casals, S. Nonell, Aromatic ketones as standards for singlet molecular oxygen O2(1Δg) photosensitization. Time-resolved photoacoustic and near-IR emission studies, J. Photochem. Photobiol., A, 1996, 97, 11–18.

    Article  Google Scholar 

  24. S. E. Braslavsky, G. E. Heibel, Time-resolved photothermal and photoacoustic methods applied to photoinduced processes in solution, Chem. Rev., 1992, 92, 1381–1410.

    Article  CAS  Google Scholar 

  25. L. J. Rothberg, J. D. Simon, M. Bernstein, K. S. Peters, Pulsed laser photoacoustic calorimetry of metastable species, J. Am. Chem. Soc., 1983, 105, 3464–3468.

    Article  CAS  Google Scholar 

  26. J. Rudzki Small, L. J. Libertini, E. W. Small, Analysis of photoacoustic waveforms using the nonlinear least squares method, Biophys. Chem., 1992, 42, 29–48.

    Article  Google Scholar 

  27. M. Mesaros, O. I. Tarzi, R. Erra-Balsells, G. M. Bilmes, The photophysics of some UV-MALDI matrices studied by using spectroscopic, photoacoustic and luminescence techniques, Chem. Phys. Lett., 2006, 426, 334–340.

    Article  CAS  Google Scholar 

  28. N. Srividya, P. Ramamurthy, V. T. Ramakrishnan, Photooxidation of acridine(1,8)dione dyes: flash photolysis investigation of the mechanistic details, Phys. Chem. Chem. Phys., 2000, 2, 5120–5126.

    Article  CAS  Google Scholar 

  29. B. Venkatachalapathy, P. Ramamurthy, Excited state proton and electron transfer reactions of acridinedione dyes with amines, Phys. Chem. Chem. Phys., 1999, 1, 2223–2230.

    Article  CAS  Google Scholar 

  30. H. Mohan, N. Srividya, P. Ramamurthy, J. P. Mittal, Kinetics and spectral characteristics of transient species formed on one-electron oxidation of acridine-1,8-dione in aqueous solution pulse radiolysis study, J. Chem. Soc., Faraday Trans., 1996, 92, 2353–2359.

    Article  CAS  Google Scholar 

  31. H. Mohan, J. P. Mittal, Electron-transfer and excited-state properties of radiolytically generated transients of acridine(1,8)dione dyes in an organic matrix, J. Photochem. Photobiol., A, 2001, 141, 25–32.

    Article  CAS  Google Scholar 

  32. Q. Li, C. Batchelor-McAuley, N. S. Lawrence, R. S. Hartshorne, R. G. Compton, 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, J. Electroanal. Chem., 2013, 688, 328–355.

    Article  CAS  Google Scholar 

  33. N. Srividya, P. Ramamurthy, P. Shanmugasundaram, V. T. Ramakrishnan, Synthesis, characterization, and electrochemistry of some acridine-1,8-dione dyes, J. Org. Chem., 1996, 61, 5083–5089.

    Article  CAS  Google Scholar 

  34. P. Murugan, P. Shanmugasundaram, V. T. Ramakrishnan, B. Venkatachalapathy, N. Srividya, P. Ramamurthy, K. Gunasekaran, D. Velmurugan, 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, J. Chem. Soc. Perkin Trans. 2., 1998, 999–1004.

    Google Scholar 

  35. J. N. Miller, Standards in fluorescence spectrometry, Chapman & Hall, London, 1981.

    Book  Google Scholar 

  36. R. Schmidt, C. Tanielian, R. Dunsbach, C. Wolff, Phenalenone, a universal reference compound for the determination of quantum yields of singlet oxygen O2(1Δg) sensitization, J. Photochem. Photobiol., A, 1994, 79, 11–17.

    Article  CAS  Google Scholar 

  37. M. Mesaros, S. M. Bonesi, M. A. Ponce, R. Erra-Balsellsv, G. M. Bilmes, The photophysics of nitrocarbazoles studied by using spectroscopic, photoacoustic and luminescence techniques, Photochem. Photobiol. Sci., 2003, 2, 808–816.

    Article  CAS  Google Scholar 

  38. P. Van Haver, L. Viaene, M. Van der Auweraes, F. C. de Schryver, References for laser-induced opto-acoustic spectroscopy using UV excitation, J. Photochem. Photobiol., A, 1990, 63, 265–277.

    Article  Google Scholar 

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Correspondence to Gabriel M. Bilmes.

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Cabanzo Hernández, R., David Gara, P.M., Velasco, D.M. et al. Photophysical behavior of new acridine(1,8)dione dyes. Photochem Photobiol Sci 12, 1968–1975 (2013). https://doi.org/10.1039/c3pp50159k

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  • DOI: https://doi.org/10.1039/c3pp50159k

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