Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access August 11, 2008

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

D. Svechkarev, G. Karpushina, L. Lukatskaya and A. Doroshenko
From the journal Open Chemistry

Abstract

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.

[1] Sengupta P.K., Kasha M., Excited state proton-transfer spectroscopy of 3-hydroxyflavone and quercetin, Chem. Phys. Lett. 68, 382 (1979) http://dx.doi.org/10.1016/0009-2614(79)87221-810.1016/0009-2614(79)87221-8Search in Google Scholar

[2] Kasha M., Proton transfer spectroscopy, J. Chem. Soc., Faraday Trans., 82, 2379–2392 (1986) http://dx.doi.org/10.1039/f2986820237910.1039/f29868202379Search in Google Scholar

[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)80157-510.1016/1010-6030(93)80157-5Search in Google Scholar

[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)80158-610.1016/1010-6030(93)80158-6Search in Google Scholar

[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) Search in Google Scholar

[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/ja00353a04710.1021/ja00353a047Search in Google Scholar

[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/j150655a01210.1021/j150655a012Search in Google Scholar

[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.2007.09.00910.1016/j.molstruc.2007.09.009Search in Google Scholar

[9] Algar J., Flynn J.P., New synthesis of flavonols, Proc. Roy. Irish. Acad. Sci., 42B, 1–8 (1934) Search in Google Scholar

[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.557005032310.1002/jhet.5570050323Search in Google Scholar

[11] Melhuish W.H., Absolute spectrofluorometry, J. Res. Nat. Bur. Stand. USA. 76A 547–560 (1972) 10.6028/jres.076A.049Search in Google Scholar PubMed PubMed Central

[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/10.1063/1.167227010.1063/1.1672270Search in Google Scholar

[13] Reichardt C., Solvatochromic dyes as solvent polarity indicators, Chem. Rev. 94, 2319–2358. (1994) http://dx.doi.org/10.1021/cr00032a00510.1021/cr00032a005Search in Google Scholar

[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/b210352d10.1039/b210352dSearch in Google Scholar

[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/jp027315g10.1021/jp027315gSearch in Google Scholar

[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)89475-910.1016/S1386-1425(97)89475-9Search in Google Scholar

[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.91.25.1196810.1073/pnas.91.25.11968Search in Google Scholar PubMed PubMed Central

[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/b107255m10.1039/b107255mSearch in Google Scholar PubMed

[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/ja00299a02410.1021/ja00299a024Search in Google Scholar

Published Online: 2008-8-11
Published in Print: 2008-9-1

© 2008 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Scroll Up Arrow