The solvatochromism and electronic structure of(E)-2-(2-hydroxystyryl)quinolin-8-ol

Abstract

The (E)-2-(2-hydroxystyryl)quinolin-8-ol (abbreviated as HSQ) molecule was synthesized and characterized. The ESIPT, solvatochromism properties, electronic structure, and ground and excited electric dipole moments of this molecule were measured using absorption and fluorescence spectra recorded in 13 different solvents. Its electronic structure via electronic transitions was investigated to find the quantitative values of solvatochromism properties by LSER calculations. The ESIPT mechanism was clarified; ground and excited dipole moments were determined using solvatochromic shift methods. The DFT (B3LYP)/6-311 ++ G(d,p) method and basis set with potential energy surface (PES) calculations of proton transfer were used to explain the ESIPT mechanism. NBO analysis, NLO properties, and behavior under an electric field were also determined.

Synthesis of Quinoline‐Pyrene Derivatives and Theoretical Investigation of Their Fluorescence and Electronic Properties

“…Nucleus independent chemical shift (NICS) was introduced by Schleyer and coworkers as a simple and efficient probe for aromaticity [37] . Thereafter, many studies have been published via computation of NICS to determine aromaticities of the related systems [38,39] . The stability of metal complexes can also be determined by investigation of chelatoaromaticity [40] .…”

“…[37] Thereafter, many studies have been published via computation of NICS to determine aromaticities of the related systems. [38,39] The stability of metal complexes can also be determined by investigation of chelatoaromaticity. [40] According to Zborowski et al aromaticity of ligands is enhanced upon complexation with cations.…”

Heterocyclic molecules with ESIPT emission: synthetic approaches, molecular diversities, and application strategies

“…In terms of ESIPT research, the most common heterocyclic compounds that have been developed are 2-(2-hydroxyphenyl)benzimidazole (HBI), 2-(2-hydroxyphenyl)benzoxazole (HBO), and 2-(2-hydroxyphenyl)benzothiazole (HBT), as well as their many derivatives. Besides these compounds, quinoline [ 2 ], benzophenone [ 3 ], flavone [ 4 ], anthraquinone [ 5 ], benzotriazole [ 6 ], quinoxaline [ 7 , 8 ], salicylidenaniline [ 9 ], pyrazole [ 10 ], and imidazolone [ 11 ] have been found to have ESIPT emission. Menges and his colleagues, on the other hand, recently found that, in addition to the ring systems indicated above, imidazole with a carbonyl in the C-2 position (CIM: C-2 carbonyl imidazole; CIN: C-2 carbonyl indole) and an indole ring with an oxalate functionality also emit ESIPT [ 12 , 13 ].…”