Ab initio study of polar and non-polar aprotic solvents effects on some 3-hydroxychromones and 3-hydroxyquinolones derivatives
The photophysical properties of some 3-hydroxychromones (3-HC) and 3-hydroxyquinolones (3-HQ) derivatives are investigated in polar and non-polar aprotic solvents using the TDDFT method and the PCM formalism. In acetonitrile and n-hexane, 2–(2-benzothienyl)-3-HC) (BTHC), 2-furyl-3-HQ (FHQ), and 1-methyl-2-furyl-3-HQ (MFHQ) have exhibited dual emission bands due to the excited state intramolecular proton transfer (ESIPT) reaction, leading to a single excited tautomer form. Our results indicate a very high BTHC light absorption efficiency and radiative rate constant. A charge transfer (CT) analysis suggests that the chromone moiety acts as an acceptor group while quinolone moiety acts as an electron donor. In addition, in non-polar n-hexane the furyl group may act as an acceptor, while in polar acetonitrile it may act as an electron donor. The energies of the upper and lower states of the normal form fluorescence have been decreased by the introduction of ortho-methyl group in FHQ. In all states, MFHQ exhibits large distortions of the dihedral angle between the chromone moiety and the furan group in para position. The ESIPT reaction is irreversible for the three derivatives in all cases studied in this work. Since experimental data with n-hexane are not available, results concerning this solvent are only predictions.
KeywordsPolar Non-polar Aprotic Solvent 3-hydroxychromone 3-hydroxyquinolone
This work was supported by LABORATOIRE D’OPTIQUE ET APPLICATIONS of CEPAMOQ. All our thanks to Université de Strasbourg for access to its facilities.
- 11.Ormson S, Brown R (1994) Excited state intramolecular proton transfer part 2: Esipt to oxygen. Prog React Kinet 19:211–275Google Scholar
- 17.Klymchenko SA, Pivovarenko GV, Demchenko PA (2003) Perturbation of planarity as the possible mechanism of solvent-dependent variations of fluorescence quantum yield in 2-aryl-3-hydroxychromones Spectrochim. Acta A Mol Biomol Spectrosc 59:787–792Google Scholar
- 25.Jensen F (2003) Introduction to computational chemistry. Wiley, ChichesterGoogle Scholar
- 33.Hang Y, Hui L, Guomin X, Chengyan R, Ying S, Hongming W, Jin M, Dajun D (2016) A novel non-fluorescent excited state intramolecular proton transfer phenomenon induced by intramolecular hydrogen bonds: an experimental and theoretical investigation. Scr Theol 6:19774Google Scholar
- 34.Shvadchak, V. V (2009) Sondes fluorescentes à émission duale pour la caractérisation d’interactions impliquant des protéines: Application aux protéines rétrovirales. PhD thesis, University of StrasbourgGoogle Scholar