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2012 | 10 | 1 | 205-215
Article title

1,4-bis-(3-hydroxy-4-oxo-4H-chromen-2-yl)-benzene (bis-flavonol): synthesis, spectral properties and principle possibility of the excited state double proton transfer reaction

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Abstracts
EN
Synthesis and systematic investigation of the spectral-luminescent properties of “bis-flavonol” {1,4-bis-(3-hydroxy-4-oxo-4H-chromen-2-yl)-benzene} were performed. Hypothetical possibility for the double excited-state proton transfer reaction in bis-flavonol is discussed based on both quantum-chemical modeling and experimental data. Consecutive S1*-state transfer of the two protons of the title molecule is shown to be energetically unfavorable, however, still preserving a possibility for the concerted double proton transfer in the excited dienol form.
Publisher
Journal
Year
Volume
10
Issue
1
Pages
205-215
Physical description
Dates
published
1 - 2 - 2012
online
24 - 11 - 2011
References
  • [1] P.M. Kiefer, V.B.P. Leite, R.M. Whitnell, Chem. Phys. 194, 33 (1995) http://dx.doi.org/10.1016/0301-0104(94)00374-J[Crossref]
  • [2] K.C. Hass, W.F. Schneider, C.M. Estevez, R.D. Bach, Chem. Phys. Lett. 263, 414 (1996) http://dx.doi.org/10.1016/S0009-2614(96)01235-3[Crossref]
  • [3] S. Santra, S.K. Dogra, Chem. Phys. 226, 285 (1998) http://dx.doi.org/10.1016/S0301-0104(97)00311-X[Crossref]
  • [4] M. Kasha, J Chem. Soc. Faraday Trans II 82, 2379 (1986) http://dx.doi.org/10.1039/f29868202379[Crossref]
  • [5] Y. Kostov, G. Rao, Rev. Sci. Instrum. 70, 4466 (1999) http://dx.doi.org/10.1063/1.1150098[Crossref]
  • [6] A.P. Demchenko, Lab Chip 5, 1210 (2005) http://dx.doi.org/10.1039/b507447a[Crossref]
  • [7] J. Catalan, J.C. Del Valle, C. Diaz, J. Palomar, J.L.G. De Paz, M. Kasha, Int. J. Quant. Chem. 72, 421 (1999) http://dx.doi.org/10.1002/(SICI)1097-461X(1999)72:4<421::AID-QUA26>3.0.CO;2-3[Crossref]
  • [8] P.-T. Chou, M. L. Martinez, J.-H. Clemens, J. Phys. Chem. 97, 2618 (1993) http://dx.doi.org/10.1021/j100113a024[Crossref]
  • [9] D. McMorrow, M. Kasha, J. Phys. Chem. 88, 2235 (1984) http://dx.doi.org/10.1021/j150655a012[Crossref]
  • [10] V.V. Shynkar, A.S. Klymchenko, E. Piemont, A.P. Demchenko, Y. Mely, J. Phys. Chem. A 108, 8151 (2004) http://dx.doi.org/10.1021/jp047990l[Crossref]
  • [11] A.D. Roshal, A.V. Grigorovich, A.O. Doroshenko, V.G. Pivovarenko, A.P. Demchenko, J. Phys. Chem. A 102, 5907 (1998) http://dx.doi.org/10.1021/jp972519w[Crossref]
  • [12] X. Poteau, G. Saroja, C. Spies, R.G. Brown, J. Photochem. Photobiol. A: Chem. 162, 431 (2004) http://dx.doi.org/10.1016/S1010-6030(03)00429-5[Crossref]
  • [13] D. Svechkarev, B. Dereka, A. Doroshenko, J. Phys. Chem. A 115, 4223 (2011) http://dx.doi.org/10.1021/jp110974n[Crossref]
  • [14] A. Sytnik, D. Gormin, M. Kasha, Proc. Natl. Acad. Sci. USA. 91, 11968 (1994) http://dx.doi.org/10.1073/pnas.91.25.11968[Crossref]
  • [15] S. Ercelen, A.S. Klymchenko, Y. Mely, A.P. Demchenko, Int. J. Biol. Macromol. 35, 231 (2005) http://dx.doi.org/10.1016/j.ijbiomac.2005.02.002[Crossref]
  • [16] A.S. Klymchenko, V.V. Shvadchak, D.A. Yushchenko, N. Jain, Y. Mely. J. Phys. Chem. B 112, 12050 (2008) http://dx.doi.org/10.1021/jp8058068[Crossref]
  • [17] D.A. Yushchenko, O.B. Vadzyuk, S.O. Kosterin, G. Duportail, Y. Mely, V.G. Pivovarenko, Anal. Biochem. 369, 218 (2007) http://dx.doi.org/10.1016/j.ab.2007.05.005[Crossref]
  • [18] A.S. Klymchenko, G. Duportail, T. Ozturk, V.G. Pivivarenko, Y. Mely, A.P. Demchenko, Chem. Biol. 9, 1199 (2002) http://dx.doi.org/10.1016/S1074-5521(02)00244-2[Crossref]
  • [19] D.A. Yushchenko, V.V. Shvadchak, M.D. Bilokin’, A.S. Klymchenko, G. Duportail, Y. Mely, V.G. Pivovarenko, Photochem. Photobiol. Sci. 5, 1038 (2006) http://dx.doi.org/10.1039/b610054f[Crossref]
  • [20] G. M’Baye, V.V. Shynkar, A.S. Klymchenko, Y. Mely, G. Duportail, J. Fluoresc. 16, 35 (2006) http://dx.doi.org/10.1007/s10895-005-0022-3[Crossref]
  • [21] V.V. Shynkar, A.S. Klymchenko, C. Kunzelmann, G. Duportail, C.D. Muller, A.P. Demchenko, J-M. Freyssinet, Y. Mely, J. Am. Chem. Soc. 129, 2187 (2007) http://dx.doi.org/10.1021/ja068008h[Crossref]
  • [22] D.A. Svechkarev, I.V. Bukatich, A.O. Doroshenko, J. Photochem. Photobiol. A: Chem. 200, 426 (2008) http://dx.doi.org/10.1016/j.jphotochem.2008.09.005[Crossref]
  • [23] A. P. Demchenko, J. Fluoresc. 20, 1099 (2010) http://dx.doi.org/10.1007/s10895-010-0644-y[Crossref]
  • [24] A.S. Klymchenko, A. P. Demchenko, Phys. Chem. Chem. Phys. 5, 461 (2003) http://dx.doi.org/10.1039/b210352d[Crossref]
  • [25] H. Zhang, P. van der Meulen, M. Glasbeek, Chem. Phys. Lett. 253, 97 (1996) http://dx.doi.org/10.1016/0009-2614(96)00213-8[Crossref]
  • [26] K. Stock, C. Schriever, S. Lochbrunner, E. Riedle, Chem. Phys. 349, 197 (2008) http://dx.doi.org/10.1016/j.chemphys.2008.03.007[Crossref]
  • [27] J. Maranon, A. Fantoni, J.R. Grigera, J. Theor. Biol. 201, 93 (1999) http://dx.doi.org/10.1006/jtbi.1999.1008[Crossref]
  • [28] M. Meuwly, A. Müller, S. Leutwyler, Phys. Chem. Chem. Phys. 5, 2663 (2003) http://dx.doi.org/10.1039/b212732f[Crossref]
  • [29] H. Sekiya, K. Sakota, J. Photochem. Photobiol. C 9, 81 (2008) http://dx.doi.org/10.1016/j.jphotochemrev.2008.04.001[Crossref]
  • [30] J.C. Hargis, E. Vohringer-Martinez, H.L. Woodcock, A. Toro-Labb, H.F. Schaefer, J. Phys. Chem. A 115, 2650 (2011) http://dx.doi.org/10.1021/jp111834v[Crossref]
  • [31] M. Glasbeek, P. Toele, H. Zhang, J. Lumin. 94–95, 623 (2001) http://dx.doi.org/10.1016/S0022-2313(01)00348-9[Crossref]
  • [32] L. Torres, M. Moreno, J.M. Lluch, Chem. Phys. Lett. 340, 591 (2001) http://dx.doi.org/10.1016/S0009-2614(01)00449-3[Crossref]
  • [33] G. Villani, Phys. Chem. Chem. Phys. 12, 2664 (2010) http://dx.doi.org/10.1039/b917672a[Crossref]
  • [34] E. Falkovskaia, V.G. Pivovarenko, J.C. del Valle, Chem. Phys. Lett. 352, 415 (2002) http://dx.doi.org/10.1016/S0009-2614(01)01490-7[Crossref]
  • [35] E. Falkovskaia, V.G. Pivovarenko, J.C. del Valle, J. Phys. Chem. A 107, 3316 (2003) http://dx.doi.org/10.1021/jp021791p[Crossref]
  • [36] V.G. Pivovarenko, L. Jozwiak, J. Blazejowski, Eur. J. Org. Chem. 2002, 3979 (2002) http://dx.doi.org/10.1002/1099-0690(200212)2002:23<3979::AID-EJOC3979>3.0.CO;2-5[Crossref]
  • [37] Y. Chauhan, M. Chaudhari, A. Dhalla, S. Maruvada, S. Naik, V. Pai-Paranjape, P. Schottland, G. Shankarling, K. Puthamane, M. Sait, US Patent 2008/0265176 A1 (issued 30 Oct. 2008)
  • [38] J. Algar, J.P. Flynn, Proc. Roy. Irish. Acad. Sci. 42B, 1 (1934)
  • [39] M.A. Smith, R.M. Neumann, R.A. Webb, J. Het. Chem. 5, 425 (1968) http://dx.doi.org/10.1002/jhet.5570050323[Crossref]
  • [40] W.H. Melhuish, J. Res. Nat. Bur. Stand. USA. 76A, 547 (1972) http://dx.doi.org/10.6028/jres.076A.049[Crossref]
  • [41] D.B. Siano, D.E. Metzler, J. Chem. Phys. 51, 1856 (1969) http://dx.doi.org/10.1063/1.1672270[Crossref]
  • [42] C. Reichardt. Chem. Rev. 94, 2319 (1994) http://dx.doi.org/10.1021/cr00032a005[Crossref]
  • [43] A.D. Becke, J. Chem. Phys. 98, 5648 (1993) http://dx.doi.org/10.1063/1.464913[Crossref]
  • [44] D.E. Woon, T.H. Dunning, J. Chem. Phys. 98, 1358 (1993) http://dx.doi.org/10.1063/1.464303[Crossref]
  • [45] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox. Gaussian 09, Revision B.01 (Gaussian, Inc., Wallingford CT, 2010)
  • [46] _E.J. Bylaska, W.A. de Jong, N. Govind, K. Kowalski, T.P. Straatsma, M. Valiev, D. Wang, E. Apra, T.L. Windus, J. Hammond, P. Nichols, S. Hirata, M.T. Hackler, Y. Zhao, P.-D. Fan, R.J. Harrison, M. Dupuis, D.M.A. Smith, J. Nieplocha, V. Tipparaju, M. Krishnan, Q. Wu, T. Van Voorhis, A.A. Auer, M. Nooijen, E. Brown, G. Cisneros, G.I. Fann, H. Fruchtl, J. Garza, K. Hirao, R. Kendall, J.A. Nichols, K. Tsemekhman, K. Wolinski, J. Anchell, D. Bernholdt, P. Borowski, T. Clark, D. Clerc, H. Dachsel, M. Deegan, K. Dyall, D. Elwood, E. Glendening, M. Gutowski, A. Hess, J. Jaffe, B. Johnson, J. Ju, R. Kobayashi, R. Kutteh, Z. Lin, R. Littlefield, X. Long, B. Meng, T. Nakajima, S. Niu, L. Pollack, M. Rosing, G. Sandrone, M. Stave, H. Taylor, G. Thomas, J. van Lenthe, A. Wong, Z. Zhang, NWChem, A Computational Chemistry Package for Parallel Computers, Version 5.1 (Pacific Northwest National Laboratory, Richland, Washington, USA, 2007)
  • [47] A.V. Luzanov, O.A. Zhikol, Int. J. Quant. Chem. 110, 902 (2010)
  • [48] R.F.W. Bader, Acc. Chem. Res. 18, 9 (1985) http://dx.doi.org/10.1021/ar00109a003[Crossref]
  • [49] R.F.W. Bader, Chem. Rev. 91, 893 (1991) http://dx.doi.org/10.1021/cr00005a013[Crossref]
  • [50] R.F.W. Bader, J. Phys. Chem. A 102, 7314 (1998) http://dx.doi.org/10.1021/jp981794v[Crossref]
  • [51] R.F.W. Bader, J. Phys. Chem. A 113, 10391 (2009) http://dx.doi.org/10.1021/jp906341r[Crossref]
  • [52] E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett. 285, 170 (1998) http://dx.doi.org/10.1016/S0009-2614(98)00036-0[Crossref]
  • [53] R. Parthasarathi, V. Subramanian, N. Sathyamurthy, J. Phys. Chem. A 110, 3349 (2006) http://dx.doi.org/10.1021/jp060571z[Crossref]
  • [54] A.O. Doroshenko, E.A. Posokhov, A.A. Verezubova, L.M. Ptyagina, V.T. Skripkina, V.M. Shershukov, Photochem. Photobiol. Sci. 1, 92 (2002) http://dx.doi.org/10.1039/b107255m[Crossref]
  • [55] A.D. Roshal, V.G. Mitina, V.D. Orlov, O.A. Ponomarev, A.A. Sukhorukov, S.V. Fialkova, Funct. Mater. 4, 121 (1997)
  • [56] A.O. Doroshenko, J. Mol. Struct. 933, 169 (2009) http://dx.doi.org/10.1016/j.molstruc.2009.06.012[Crossref]
  • [57] D. McMorrow, M. Kasha, J. Phys. Chem. 88, 2235 (1984) http://dx.doi.org/10.1021/j150655a012[Crossref]
  • [58] A. Douhal, M. Sanz, L. Tormo, J.A. Organero, Chem. Phys. Chem. 6, 419 (2005) http://dx.doi.org/10.1002/cphc.200400375[Crossref]
  • [59] L. Tormo, A. Douhal, J. Photochem. Photobiol., A: Chem. 173, 358 (2005) http://dx.doi.org/10.1016/j.jphotochem.2005.04.015[Crossref]
  • [60] S. Protti, A. Mezzetti, J-P. Cornard, C. Lapouge, M. Fagnoni, Chem. Phys. Lett. 467, 88 (2008) http://dx.doi.org/10.1016/j.cplett.2008.11.005[Crossref]
  • [61] P.K. Mandal, A. Samanta, J. Phys. Chem. A 107, 6334 (2003) http://dx.doi.org/10.1021/jp027613d[Crossref]
  • [62] V.I. Tomin, R. Javorski, Opt. Spectr. (Engl. Ed.) 102, 242 (2007) http://dx.doi.org/10.1134/S0030400X07020129
  • [63] L.V. Chepeleva, A.Y. Matsakov, Z.A. Kondratyuk, F.G. Yaremenko, A.O. Doroshenko, J. Photochem. Photobiol. A: Chem. 209, 163 (2010) http://dx.doi.org/10.1016/j.jphotochem.2009.11.010[Crossref]
  • [64] A.R. Katritzky, D.C. Fara, H. Yang, K. Tamm, T. Tamm, M. Karelson, Chem. Rev. 104, 175 (2004) http://dx.doi.org/10.1021/cr020750m[Crossref]
  • [65] J. Catalan, J. Phys. Chem. B 113, 5951 (2009) http://dx.doi.org/10.1021/jp8095727[Crossref]
  • [66] D. Le Gourrierec, S.M. Ormson, R.G. Brown, Progr. React. Kinet. 19, 221 (1994)
  • [67] S.J. Formosinho, L.G. Arnaut, J. Photochem. Photobiol. A: Chem. 75, 21 (1993) http://dx.doi.org/10.1016/1010-6030(93)80158-6[Crossref]
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bwmeta1.element.-psjd-doi-10_2478_s11532-011-0127-2
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