Substituent effects on the photophysical properties of amino-aurone-derivatives

Muñoz-Becerra K.; Villegas-Escobar N.; Zúñiga-Loyola C.; Cortés-Arriagada D.; Toro-Labbé A.

Abstract

Aurones are potential candidates to be employed as fluorescent probes or as pharmacophores for biological applications. This work describes a density functional theory (DFT) and time-dependent -DFT study at the PBE0/6-31+G(d) level of theory to analyse the structural, electronic and photophysical properties of a series of new proposed 4-amine-aurone derivatives in its E and Z isomeric conformations. The maximum absorption wavelength of the proposed aurones appears in the range 390-514nm, while the most allowed emission pathways were computed in the range 493-530nm. The bathochromic shift of these compounds with respect to the non-substituted aurone is modulated by the acceptor strength of the added 4-substituents, in addition to the ability of the substituents to localise the frontier molecular orbitals over the acceptor benzofuranone moiety without losing the tricyclic planarity, which favours the push-pull nature of these molecules. The influence of the 4-substituent is also evidenced in the Stokes shifts for the whole series; as the electron-withdrawing character of the 4-substituents enhances, higher is the polarisation of the structure resulting in higher Stokes shifts. As a result, -CF3 and -NO2 substituents were responsible of larger Stokes shifts, then compounds containing these substituents are proposed as potential fluorescence probes for useful applications in biological systems. [GRAPHICS] .

Más información

Título según WOS: Substituent effects on the photophysical properties of amino-aurone-derivatives
Título según SCOPUS: Substituent effects on the photophysical properties of amino-aurone-derivatives
Título de la Revista: MOLECULAR PHYSICS
Volumen: 117
Número: 09-dic
Editorial: TAYLOR & FRANCIS LTD
Fecha de publicación: 2018
Idioma: English
DOI:

10.1080/00268976.2018.1559372

Notas: ISI, SCOPUS