A Theoretical Study of Solvent Effects on the Structure and UV–vis Spectroscopy of 3-Hydroxyflavone (3-HF) and Some Simplified Molecular Models

Abstract

Solvent effects on the UV–vis spectra of 3-hydroxyflavone and other structurally related molecules (3-hydroxychromen-4-one, 3-hydroxy-4-pyrone, and 4-pyrone) have been studied by combining time-dependent density functional theory (TDDFT) and the polarizable continuum method (PCM). Among the first five excited states of the four considered molecules, electronic states of n → π* and π → π* nature appear. In general, the stability of the n → π* states decreases as the π space becomes larger in such a way that only for 4-pyrone and 3-hydroxy-4-pyrone are they the first excited states. In addition, they become less stabilized in ethanol solution than the ground state, and this causes blueshift transitions in solution. The opposite trend is found for the π → π* excited states. They are less energetic with the π-system size and when passing from gas phase to solution. The solvent shift also depends strongly on the size of the π systems and on the formation of an intramolecular hydrogen bond; thus, it decreases when going from 4-pyrone to 3-hydroxyflavone. The performance of the three versions (cLR, cLR2, and IBSF) of the specific-state PCM method in predicting transition energies are compared.

In Vitro and in Silico Studies of 3‐Hydroxyflavone‐Based Sulfonate Esters: Potent Acetylcholinesterase, Carbonic Anhydrase and α‐Glycosidase Inhibitors

“…These rings and chains are linked together by various types of bonds. [17] In the recent year, the synthesis of some sulfonate ester derivatives has gained significant attention from researchers. This class of molecules has quickly become prominent in the field due to their importantant biological activity, [18][19][20][21][22] as presented in Figure 2.…”

“…The structure of 3‐hydroxyflavone is based on a 15‐carbon skeleton consisting of three rings (A, B, and C) and one open chain (Figure 1). These rings and chains are linked together by various types of bonds [17] …”