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2008 | 6 | 3 | 443-449
Tytuł artykułu

2-(benzimidazol-2-yl)-3-hydroxychromone derivatives: spectroscopic properties and a possibile alternative intramolecular proton phototransfer

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Three 2-(benzimidazol-2-yl)-3-hydroxychromone derivatives were synthesized. Their spectroscopic and fluorescent properties, due to excited state intramolecular proton transfer (ESIPT) from OH to carbonyl, were studied. Theoretical possibility of an alternative intramolecular H-bonding and experimental evidence for such behavior are discussed. [...]
Wydawca

Czasopismo
Rocznik
Tom
6
Numer
3
Strony
443-449
Opis fizyczny
Daty
wydano
2008-09-01
online
2008-08-11
Twórcy
  • Institute for Chemistry at Kharkov V.N. Karazin National University, 61077, Kharkov, Ukraine
  • Institute for Chemistry at Kharkov V.N. Karazin National University, 61077, Kharkov, Ukraine
  • Institute for Chemistry at Kharkov V.N. Karazin National University, 61077, Kharkov, Ukraine
Bibliografia
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  • [2] Kasha M., Proton transfer spectroscopy, J. Chem. Soc., Faraday Trans., 82, 2379–2392 (1986) http://dx.doi.org/10.1039/f29868202379[Crossref]
  • [3] Arnaut L.G., Formosinho S.J., Excited state proton transfer reactions. I. Fundamentals and intramolecular reactions, J. Photochem. Photobiol., A:Chem. 75, 1–20 (1993) http://dx.doi.org/10.1016/1010-6030(93)80157-5[Crossref]
  • [4] Formosinho S.J., Arnaut L.G., Excited state proton transfer reactions. II. Intramolecular reactions, J. Photochem. Photobiol., A:Chem. 75, 21–48 (1993) http://dx.doi.org/10.1016/1010-6030(93)80158-6[Crossref]
  • [5] LeGourrierec D., Ormson S.M., Brown R.G., Excited state intramolecular proton transfer. Part 2: ESIPT to oxygen, Progr. React. Kinet. 19, 221–295(1994)
  • [6] McMorrow D., Kasha M., Proton-transfer spectroscopy of 3-hydroxychromones. Extreme sensitivity to hydrogen-bonding perturbations, J. Amer. Chem. Soc. 105, 5134–5135 (1983) http://dx.doi.org/10.1021/ja00353a047[Crossref]
  • [7] McMorrow D., Kasha M., Intramolecular excitedstate proton transfer in 3-hydroxyflavone. Hydrogenbonding solvent perturbations, J. Phys. Chem. 88, 2235–2243 (1984) http://dx.doi.org/10.1021/j150655a012[Crossref]
  • [8] Svechkarev D. A., Baumer V. N., Syzova Z. A., Doroshenko A. O., New benzimidazolic 3-hydroxychromone derivative with two alternative mechanisms of the excited state intramolecular proton transfer reaction, J. Mol. Struct, 882, 63–69 (2008) http://dx.doi.org/10.1016/j.molstruc.2007.09.009[WoS][Crossref]
  • [9] Algar J., Flynn J.P., New synthesis of flavonols, Proc. Roy. Irish. Acad. Sci., 42B, 1–8 (1934)
  • [10] Smith M.A., Neumann R.M., Webb R.A., A modification of the Algar-Flynn-Oyamada preparation of flavonols, J. Het. Chem. 5, 425–426 (1968) http://dx.doi.org/10.1002/jhet.5570050323[Crossref]
  • [11] Melhuish W.H., Absolute spectrofluorometry, J. Res. Nat. Bur. Stand. USA. 76A 547–560 (1972) [Crossref]
  • [12] Siano D.B., Metzler D.E., Band shapes of the electronic spectra of complex molecules, J. Chem. Phys. 51, 1856–1861 (1969) http://dx.doi.org/10.1063/1.1672270[Crossref]
  • [13] Reichardt C., Solvatochromic dyes as solvent polarity indicators, Chem. Rev. 94, 2319–2358. (1994) http://dx.doi.org/10.1021/cr00032a005[Crossref]
  • [14] Klymchenko A.S., Demchenko A.P., Multiparametric probing of intermolecular interactions with fluorescent dye exhibiting excited state intramolecular proton transfer, Phys. Chem. Chem. Phys. 5, 461–468 (2003) http://dx.doi.org/10.1039/b210352d[Crossref]
  • [15] Klymchenko A.S., Pivovarenko V.G., Demchenko A.P., Elimination of the hydrogen bonding effect on the solvatochromism of 3-hydroxyflavones, J. Phys. Chem. A. 107, 4211–4216 (2003) http://dx.doi.org/10.1021/jp027315g[Crossref]
  • [16] Guharay J., Sengupta P.K., Excited-state proton transfer and dual fluorescence of robinetin in different environments, Spectrochim. Acta, Part A. 53, 905–912 (1997) http://dx.doi.org/10.1016/S1386-1425(97)89475-9[Crossref]
  • [17] Sytnik A., Gormin D., Kasha M., Interplay between excited-state intramolecular proton transfer and charge transfer in flavonols and their use as protein-binding-site fluorescent probes, Proc. Natl. Acad. Sci. USA. 91, 11968–11972 (1994) http://dx.doi.org/10.1073/pnas.91.25.11968[Crossref]
  • [18] Doroshenko A.O., Posokhov E.A., Verezubova A.A., Ptyagina L.M., Skripkina V.T., Shershukov V.M., Radiationless deactivation of the excited phototautomer form and molecular structure of ESIPT-compounds, Photochem. Photobiol. Sci. 1, 92–99 (2002) http://dx.doi.org/10.1039/b107255m[Crossref]
  • [19] Dewar M.J.S., Zoebich E.G., Healy E.F., AM1: a new general purpose quantum mechanical molecular model, J. Amer. Chem. Soc. 107, 3902–3908 (1985) http://dx.doi.org/10.1021/ja00299a024[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-008-0039-y
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