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

Ayşegül Gümüş,Selçuk Gümüş,Yadigar Gülseven Sidir,İsa Sidir

doi:10.3906/kim-1903-36

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.

Highlights

Quinoline derivatives have been used in many different applications such as optoelectronic materials and optical switches in nonlinear optics due to their unique electronic structure [1,2]
The HSQ was synthesized by the reaction of 2-methyl quinoline-8-ol and salicylaldehyde by the catalysis of Ca(OTf) 2 (Scheme)
The first electronic absorbance transition peak observed in the absorbance spectrum can be referred to as π –π * electronic transition, which was observed in cyclohexane, diethyl ether, methanol, acetonitrile, ethylene glycol, and water

Summary

Introduction

Quinoline derivatives have been used in many different applications such as optoelectronic materials and optical switches in nonlinear optics due to their unique electronic structure [1,2] These compounds have some biological activities such as anticancer potential [1,3] and are used in the treatment of malaria, topical pathogenic parasitic Leishmania infection, antihepatitis B, etc. All extracts were dried over anhydrous magnesium sulfate and solutions were concentrated under reduced pressure using a rotary evaporator Both absorbance and fluorescence spectra were recorded in cyclohexane, benzene, toluene, o-xylene, diethyl ether, chloroform, 1-butanol, acetone, ethanol, methanol, acetonitrile, ethylene glycol, and water. In Catalan solvatochromism, C 6 (polarizability of solvent) and C 7 (dipolarity of solvent) solvatochromic coefficients indicate the global interactions, while C 8 (solvent of acidity) and C 9 (solvent of basicity) describe the nonglobal interactions, which occur during electronic transitions between solvent and solute [51]

Quantum chemical calculations

Results and discussion

Solvatochromism

Methods

Electric dipole moments

Conclusions