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Peculiarities of exited state intramolecular proton transfer in 2-amino-3-(2′-benzazolyl)-quinolines

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Abstract

It has been shown that a low fluorescence quantum yield of 2-amino-3-(2′-benzoxazolyl)-quinoline (ABO) and 2-amino-3-(2′-benzothiazolyl)-quinoline (ABT) is due to the relaxation process caused by excited state intramolecular proton transfer (ESIPT). Quantum-chemical calculations have revealed that ESIPT in these compounds is characterized by overcoming a potential barrier, with the lower basicity of the proton-accepting moiety in ABO resulting in a higher barrier than in ABT and, thereby, determining a substantial difference in their fluorescence quantum yields.

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References

  1. Weller, A., Z. Elektrochem. Ber. Bunsenges. Phys. Chem., 1956, vol. 60, no. 9/10, p. 1144.

    CAS  Google Scholar 

  2. Luber, S., Adamczyk, K., Nibbering, E.T.J., and Batista, V.S., J. Phys. Chem. A, 2013, vol. 117, no. 25, p. 5269.

    Article  CAS  Google Scholar 

  3. Clementi, C., Cesaretti, A., Carlotti, B., and Elisei, F., J. Phys. Chem. A, Article ASAP. doi 10.1021/acs.jpca.5b12707

  4. Furukawa, K., Hino, K., Yamamoto, N., Awasthi, K., Nakabayashi, T., Ohta, N., and Sekiya, H., J. Phys. Chem. A, 2015, vol. 119, no. 37, p. 9599.

    Article  CAS  Google Scholar 

  5. Nagaoka, S., Endo, H., Ohara, K., and Nagashima, U., J. Phys. Chem. B, 2015, vol. 119, no. 6, p. 2525.

    Article  CAS  Google Scholar 

  6. Wang, Y., Hu, Y., Wu, T., Zhou, X., and Shao, Y., Anal. Chem., 2015, vol. 87, no. 23, p. 11620.

    Article  CAS  Google Scholar 

  7. Tseng, H.-W., Shen, J.-Y., Kuo, T.-Y., Tu, T.-S., Chen, Y.-A., Demchenko, A.P., and Chou, P.-T., Chem. Sci., 2016, vol. 7, no. 1, p. 655.

    Article  CAS  Google Scholar 

  8. Demchenko, A.P., Tang, K.-C., and Chou, P.-T., Chem. Soc. Rev., 2013, vol. 42, no. 3, p. 1379.

    Article  CAS  Google Scholar 

  9. Chou, P., McMorrow, D., Aartsma, T., and Kasha, M., J. Phys. Chem., 1984, vol. 88, no. 20, p. 4596.

    Article  CAS  Google Scholar 

  10. Chou, P., Martinez, M., and Clements, J., J. Chem. Phys. Lett., 1993, vol. 204, no. 5/6, p. 395.

    Article  CAS  Google Scholar 

  11. Chou, P., Martinez, M., and Clements, J., J. Phys. Chem., 1993, vol. 97, no. 11, p. 2618.

    Article  CAS  Google Scholar 

  12. Catalan, J., Fabero, F., Claramunt, R., Santa, M., Foces-Foces, M., and Cano, F., J. Am. Chem. Soc., 1992, vol. 114, no. 13, p. 5039.

    Article  CAS  Google Scholar 

  13. Stueber, G., Kieninger, M., Schetter, H., Busch, W., Goella, B., Franke, J., Kramer, H., Horer, H., and Henele, S., J. Phys. Chem., 1995, vol. 99, no. 25, p. 10097.

    Article  CAS  Google Scholar 

  14. Scherl, M., Haarer, D., Fischer, J., DeCian, A., Lehn, J.-L., and Eichen, Y., J. Phys. Chem., 1996, vol. 100, no. 40, p. 16175.

    Article  CAS  Google Scholar 

  15. Demchenko, A.P., FEBS Lett., 2006, vol. 580, no. 12, p. 2951.

    Article  CAS  Google Scholar 

  16. Li, X., Hu, B., Li, J., Lu, P., and Wang, Y., Sens._Actuators B, 2014, vol. 203, p. 635.

    Article  CAS  Google Scholar 

  17. Lin, W.-C., Fang, S.-K., Hu, J.-W., Tsai, H.-Y., and Chen, K.-Y., Anal. Chem., 2014, vol. 86, no. 10, p. 4648.

    Article  CAS  Google Scholar 

  18. Uzhinov, B.M. and Khimich, M.N., Usp. Khim., 2011, vol. 80, no. 6, p. 580.

    Article  Google Scholar 

  19. Bisht, P.B., Petek, H., Yoshihara, K., and Nagashima, U., J. Chem. Phys., 1995, vol. 103, no. 13, p. 5290.

    Article  CAS  Google Scholar 

  20. Lochbrunner, S., Wurzer, A., and Riedle, E., J. Phys. Chem. A, 2003, vol. 107, no. 49, p. 10580.

    Article  CAS  Google Scholar 

  21. Khimich, M.N., Gostev, F.E., Shelaev, I.V., Sarkisov, O.M., Birgen, E.A., Bolotin, B.M., and Uzhinov, B.M., High Energy Chem., 2010, vol. 44, no. 6, p. 482.

    Article  CAS  Google Scholar 

  22. Mednykh, Yu.A., Khimich, M.N., Marevtsev, V.S., Gostev, F.E., Petrukhin, A.N., Sarkisov, O.M., and Uzhinov, B.M., Abstracts of Papers, The 5th International Conference on Energy Storage & Applied Photochemistry, 2003, p. 83.

    Google Scholar 

  23. Khimich, M.N. and Uzhinov, B.M., Int. J. Photoenergy, 2006, vol. 2006.

  24. Bardez, E., Devol, I., Larrey, B., and Valeur, B., J. Phys. Chem. B, 1997, vol. 101, no. 39, p. 7786.

    Article  CAS  Google Scholar 

  25. Lan, S.-C. and Liu, Y.-H., Spectrochim. Acta A, 2015, vol. 139, p. 49.

    Article  CAS  Google Scholar 

  26. Khimich, M.N., Birgen, E.A., Bolotin, B.M., Uzhinova, L.D., Kuznetsov, A.S., Zhadanov, B.V., and Uzhinov, B.M., High Energy Chem., 2010, vol. 44, no. 6, p. 492.

    Article  CAS  Google Scholar 

  27. Melhuish, W.H., J. Phys. Chem., 1961, vol. 65, no. 2, p. 229.

    Article  CAS  Google Scholar 

  28. Nemukhin, A.V., Grigorenko, B.L., and Granovskii, A.A., Vestn. Mosk. Univ., Ser. 2: Khim., 2004, vol. 45, no. 2, p. 75.

    Google Scholar 

  29. Granovsky, A.A., J. Chem. Phys., 2011, vol. 134, no. 21, p. 214113.

    Article  Google Scholar 

  30. Khimich, M.N., Birgen, E.A., Bolotin, B.M., and Uzhinov, B.M., High Energy Chem., 2009, vol. 43, no. 2, p. 123.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Moscow State University, Moscow, 119991, Russia

    M. N. Khimich, V. L. Ivanov, M. Ya. Mel’nikov & B. M. Uzhinov

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  1. M. N. Khimich
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  2. V. L. Ivanov
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  3. M. Ya. Mel’nikov
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  4. B. M. Uzhinov
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Correspondence to M. N. Khimich.

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Original Russian Text © M.N. Khimich, V.L. Ivanov, M.Ya. Mel’nikov, B.M. Uzhinov, 2017, published in Khimiya Vysokikh Energii, 2017, Vol. 51, No. 1, pp. 20–26.

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Khimich, M.N., Ivanov, V.L., Mel’nikov, M.Y. et al. Peculiarities of exited state intramolecular proton transfer in 2-amino-3-(2′-benzazolyl)-quinolines. High Energy Chem 51, 17–23 (2017). https://doi.org/10.1134/S0018143916060059

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