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Solvent effects of photoinduced electron transfer reactions of triplet fluorenone with amines

  • Article
  • Organic Chemistry
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Chinese Science Bulletin

Abstract

The property of the lowest excited triplet state of fluorenone (FL) in acetonitrile, ethyl acetate, toluene, cyclohexane has been investigated using time-resolved laser flash photolysis. The appearances of the corresponding cation radicals and anion radicals suggest that the electron transfer reaction occurs between 3FL* and amines. Experimental results show a decrease in the quenching rate constants along with reducing solvent polarity. The change of quenching rate constants of the FL excited triplet with the three N,N-dimethylaniline derivatives are explained using the Hammett constant.

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References

  1. Lathioor E C, Leigh W J. Bimolecular hydrogen abstraction from phenols by aromatic ketone triplets. Photochem Photobiol, 2006, 82: 291–300

    Article  Google Scholar 

  2. Pan Y, Sheng Z Y, Ye X D, et al. Photochemistry of quinoxaline derivatives and mechanism of the triplet state quenching by electron-poor alkenes. Photochem Photobiol A: Chem, 2005, 174: 98–105

    Article  Google Scholar 

  3. Scaiano J C. Solvent effects in the photochemistry of xanthone. J Am Chem Soc, 1980, 102: 7747–7753

    Article  Google Scholar 

  4. Pan Y, Fu Y, Liu S X, et al. Studies on photoinduced H-atom and electron transfer reactions of o-naphthoquinones by laser flash photolysis. J Phys Chem A, 2006, 110: 7316–7322

    Article  Google Scholar 

  5. Hoffmann N, Görner H. Photoinduced electron transfer from N-methylpyrrolidine to ketones and radical addition to an electron-deficient alkene. Chem Phys Lett, 2004, 383: 451–455

    Article  Google Scholar 

  6. Devadoss C, Fessenden R W. Picosecond and nanosecond studies of the photoreduction of benzophenone by 1,4-diazabicyclo[2.2.2]-octane (DABCO): Characterization of the transient. J Phys Chem, 1990, 94: 4540–4549

    Article  Google Scholar 

  7. Pan Y, Gao Y H, Yan L, et al. Reactivity of aromatic amines with triplet 1,8-dihydroxyanthraquinone: A laser flash photolysis study. Spectrochimi Acta Part A: Mol Biomol Spectro, 2007, 66: 63–67

    Article  Google Scholar 

  8. Sheng Z Y, Pan Y, Yan L Q, et al. Steady-state and laser flash photolysis studies on the oxidative splitting of cyclobutane thymine dimer by triplet 9,10-anthraquinone-2-sulfonate. J Photochem Photobiol A: Chem, 2004, 161: 99–104

    Article  Google Scholar 

  9. Wang J T, Pan Y, Zhang L M, et al. Photoinduced electron and H-atom transfer reactions of xanthone by laser flash photolysis. Chin J Chem Phys, 2007, 20: 395–400

    Article  Google Scholar 

  10. Andrews L J, Deroulede A, Linschltz H. Photophysical processes in fluorenone. J Phys Chem, 1978, 82: 2304–2309

    Article  Google Scholar 

  11. Samant V, Singh A K, Ramakrishna G, et al. Ultrafast intermolecular hydrogen bond dynamics in the excited state of fluorenone. J Phys Chem A, 2005, 109: 8693–8704

    Article  Google Scholar 

  12. Nakajima A. A laser-photolytic study of 9-fluorenone. Preliminary observations of transient absorption spectra. Mol Photochem, 1976, 7: 251–262

    Google Scholar 

  13. Greene B I, Hochstrasser R M, Weisman R B. Picosecond transient spectroscopy of molecules in solution. J Chem Phys. 1979, 70: 1247–1259

    Article  Google Scholar 

  14. Misra T, Maiti M, Saini R D, et al. Photophysical investigations on some synthesized electron donor aryl-briged compounds. J Lumin, 2003, 101: 123–134

    Article  Google Scholar 

  15. Maiti M, Misra T, Sinha S, et al. Photoinduced electron transfer (ET) within some novel synthesized derivatives of phenanthrene acting as donors and 9-fluorenone/9-cyanoanthracene behaving as acceptors. J Lumin, 2001, 93: 261–274

    Article  Google Scholar 

  16. Misra T, De A K, Pal S K, et al. Photophysical properties of 5-hydroxyindole (5HI): Laser flash photolysis study. Proc Indian Acad Sci, 2002, 114: 547–556

    Article  Google Scholar 

  17. Scaiano J C, Tanner M, Weir D. Exploratory study of the intermolecular reactivity of excited diphenylmethyl radicals. J Am Chem Soc, 1985, 107: 4396–4403

    Article  Google Scholar 

  18. Nad S, Pal H. Electron transfer from aromatic amines to excited coumarin dyes: Fluorescence quenching and picosecond transient absorption studies. J Phys Chem A, 2000, 104: 673–680

    Article  Google Scholar 

  19. Hamanoue K, Nakayama T, Asada S, et al. Electron transfer from ground-state triethylamine to the second and lowest excited triplet states of haloanthraquinones (1-chloro, 2-chloro, 1,5-dichloro, 1,8-dichloro, and 1,8-dibromo compounds) in acetonitrile at room temperature studied by picosecond and nanosecond laser spectroscopy. J Phys Chem, 1992, 96: 3736–3741

    Article  Google Scholar 

  20. Lide D R. CRC Handbook of Chemistry and Physics. 90th ed. Boca Raton: CRC Press, 2009. 15

    Google Scholar 

  21. Rehm D, Weller A. Kinetics of fluorescence quenching by electron and hydrogen-atom transfer. Isr J Chem, 1970, 8: 259–271

    Google Scholar 

  22. Zhao G J, Han K L. Ultrafast Hydrogen bond strengthening of the photoexcited fluorenone in the alcohols for facilitating the fluorescence quenching. J Phys Chem A, 2007, 111: 9218–9223

    Article  Google Scholar 

  23. Biczok L, Berces T, Linschitz H. Quenching processes in hydrogen-bonded pairs: Interactions of excited fluorenone with alcohols and phenols. J Am Chem Soc, 1997, 119: 11071–11077

    Article  Google Scholar 

  24. Abraham M H, Duce P P, Prior D V. Hydrogen Bonding. Part 9. Solute proton donor and proton acceptor scales for use in drug design. J Chem Soc Perkin Trans II, 1989, 1355–1375

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Authors and Affiliations

  1. Department of Chemical Physics, University of Science and Technology of China, Hefei, 230026, China

    JinTing Wang, Qian Sun, LiMin Zhang & ShuQin Yu

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  1. JinTing Wang
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  2. Qian Sun
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  3. LiMin Zhang
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  4. ShuQin Yu
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Correspondence to ShuQin Yu.

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Wang, J., Sun, Q., Zhang, L. et al. Solvent effects of photoinduced electron transfer reactions of triplet fluorenone with amines. Chin. Sci. Bull. 55, 2891–2895 (2010). https://doi.org/10.1007/s11434-010-3165-9

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  • DOI: https://doi.org/10.1007/s11434-010-3165-9

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