Solvatochromic studies of biologically active iodinated 4-aryloxymethyl coumarins and estimation of dipole moments

Raghavendra, U.; Basanagouda, Mahantesha; Melavanki, Raveendra; Fattepur, R. H.; Thipperudrappa, J.

doi:10.1016/j.molliq.2014.12.003

Cited by 35 publications

(14 citation statements)

References 60 publications

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“…Positive solvatochromism of up to 70 nm was observed for all three compounds from nonpolar to polar solvents suggesting that dielectric constant and refractive index of the solvents play an important role to observe bathochromically shifted emissions. Hence, we have plotted graphs of Lippert Mataga and Mac Raeplot in which Lippert Mataga or Mac‐Rae function verses Stokes shift values were plotted to check the relationship of these functions with Stokes shift . As Lippert‐Mataga represents solely solvent‐solvent interaction while in the Mac‐Rae equation solute‐solvent interaction also included, while for Weller and Rettig plot emission values were used values for regression constant were observed around 0.7‐0.8 which indicates that compounds show active charge transfer takes place from donor to acceptor.…”

Section: Resultsmentioning

confidence: 99%

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

2019

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Three novel hydroxyl substituted and triphenylamine sidearm coumarin decorated molecules were prepared to examine the effect of adjacent hydroxyl substituent as well as coumarin units on the photophysical linear and nonlinear optical properties. Both hydroxyl function adjacent to the phenyl ring and extra coumarin unit is attributed to the red shifted absorption (435‐487 nm) and emission (496‐578 nm) compared to the plain triphenylamine based coumarin derivatives. Positive solvatochromism around 70 nm was observed in solvents with different polarity polarities and it is reinforced by solvent polarity plots and multilinear regression study. Very high viscosity induced emission enhancement (5.7 – 8.2 fold) was observed for in ethanol/polyethylene glycol‐400 system, highlighting their capability to act as efficient fluorescent molecular rotors (FMRs). The nonlinear optical properties were investigated by solvatochromism as well as a computational method using B3LYP 6–311++G (d, p) basis set. All these compounds exhibited large magnitudes of first order (65‐208x10 −30e.s.u) and second order (560‐2120x10 −36e.s.u) hyperpolarizability.

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Section: Resultsmentioning

confidence: 99%

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

2019

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“…However, the influence of solvent basicity and dipolarity/ polarizability cannot be ignored. The influence of solvent polarizability is greater than that of the dipolarity and basicity (28).…”

Section: Correlation With the Multiparameter Solvent Polarity Scalementioning

confidence: 89%

“…The influence of solvent polarizability is greater than that of the dipolarity and basicity (28). The analysis was carried out by means of a multiple linear regression method using the values of α, β and π* (27) for the spectral property Δv.…”

Section: Correlation With the Multiparameter Solvent Polarity Scalementioning

confidence: 99%

Specific interactions of alcohols and non‐alcohols with a biologically active boronic acid derivative: a spectroscopic study

et al. 2015

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The photophysical properties of 4-fluoro-2-methoxyphenyl boronic acid (4FMPBA) are characterized using absorption and fluorescence techniques in series of non-alcohols and alcohols. The results are analyzed using different solvent polarity functions and Kamlet and Catalan's multiple regression approaches. The excited state dipole moment and change in dipole moment are calculated using both the solvatochromic shift method and Reichardt's microscopic solvent polarity parameter ETN. The ground state dipole moment is evaluated using quantum chemical calculations. It is found that general solute-solvent and hydrogen bond interactions are operative in this system. A red shift of ~ 9 nm in the emission spectra is observed with an increase in the solvent polarity, which depicts π→π(*) transitions, as well as the possibility of an intramolecular charge transfer (ICT) character in the emitting singlet state of 4FMPBA. The relative quantum yield, radiative and non-radiative decay constants are calculated in alkanes and alcohols using the single point method. It is found that the quantum yield of the molecule varies from 16.81% to 50.79% with the change in solvent polarity, indicating the dependence of fluorescence on the solvent environment. Copyright © 2015 John Wiley & Sons, Ltd.

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“…The knowledge of the excited state dipole moment of the molecule would be helpful in explaining the nature of excited states, in describing the course of its photophysical/photochemical transformations, and in designing the nonlinear optical devices, and it allows one to judge the site of attack by electrophilic and nucleophilic reagents in photochemical reactions, etc. [18][19][20][21][22][23][24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Modulation of benzofuran structure as a fluorescent probe to optimize linear and nonlinear optical properties and biological activities

Krawczyk

2020

J Mol Model

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The study presents the influence of structure modulation by introducing selected donor and acceptor substituents on optical properties of benzofuran used in biological imaging. As the starting form, 2-(5-formylbenzofuran-2-yl)acetamide described experimentally was used. This molecule contains an aldehyde group as reactive site, through which conjugation with protein occurs. Structure modulation was carried out by attaching additional electron-donating and electron-withdrawing substituents to the amino group, namely -NH2, -NHCH3, -NO2, -OH, and -OCH3. Studies have shown that the -NH2, -NHCH3, -OH, and -OCH3 substituents do not induce a significant change in the position of maximum absorption and fluorescence relative to each other. They also do not change the parameters describing the nonlinear response. Only the presence of the -NO2 substituent results in significant solvatochromic shifts. Changing substituents also does not significantly affect the LD50 value, and all tested fluorescent probes should not be considered toxic to humans. Modulation of the benzofuran derivative structure also does not change the active center in which the biocomplex with the protein is formed. In each case, the conjugation takes place via LYS114. In addition, the study was prompted to analyze the linear and nonlinear optical properties of conjugates formed after the reaction with Concanavalin A. Graphical abstract

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Solvatochromic studies of biologically active iodinated 4-aryloxymethyl coumarins and estimation of dipole moments

Cited by 35 publications

References 60 publications

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

Specific interactions of alcohols and non‐alcohols with a biologically active boronic acid derivative: a spectroscopic study

Modulation of benzofuran structure as a fluorescent probe to optimize linear and nonlinear optical properties and biological activities

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