Synthesis and photophysical properties of a novel phthalimide derivative using solvatochromic shift method for the estimation of ground and singlet excited state dipole moments

Akshaya, K. B.; Varghese, Anitha; Lobo, Prajwal L.; Kumari, R. Ananda; George, Louis

doi:10.1016/j.molliq.2016.09.115

Cited by 31 publications

(6 citation statements)

References 31 publications

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“…The ground state dipole moment (µ gs ) is calculated from the dielectric measurements in dilute solutions using number of methods. One of such method is Guggenheim method 36 .…”

Section: Methods IImentioning

confidence: 99%

Studies on Photophysical Properties of Mono-carbonyl Curcumin Analogues: Experimental and Theoretical approach

2018

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The solvatochromic fluorescence behaviour of mono-carbonyl curcumin analogues has been studied in ten different solvents ranging from non-polar to polar. The solvent effect on the spectral properties of analogues has been discussed. The ground state dipole moments were estimated experimentally by Bilot-Kawski equation which is a function of Stokes shift with the solvent polarity parameters and Guggenheim method and theoretically by TD-DFT studies. The excited state dipole moment was determined using Bilot-Kawski equations. The excited state dipole moments for the two molecules were found to be higher than their corresponding ground state dipole moments. Theoretically Frontier molecular orbital (HOMO/ LUMO) energies were determined by Gaussian 09 W software using TD-DFT.

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“…The ground state dipole moment (µ gs ) is calculated from the dielectric measurements in dilute solutions using number of methods. One of such method is Guggenheim method 36 .…”

Section: Methods IImentioning

confidence: 99%

Studies on Photophysical Properties of Mono-carbonyl Curcumin Analogues: Experimental and Theoretical approach

2018

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“…Due to the resistance that hardness provides throughout the chemical process, the distortion of the chemical system's electron cloud under mild disturbance is seen. Larger HOMO-LUMO gaps are seen in hard molecules, whereas smaller gaps are found in soft molecules that are more reactive [32][33] . Hard molecules are comparatively small and significantly less polarizable than soft molecules, which are big and highly polarizable.…”

Section: Global Chemical Reactivity Descriptor (Gcrd) Parametersmentioning

confidence: 99%

Designing Highly Fluorescent BenzoCoumarin‐Sesamol Conjugates for Optoelectronic Applications

Madar,

Pujar,

A. H.

et al. 2024

ChemistrySelect

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In this report we have studied, the substitutional effect on photophysical properties of newly synthesized isomeric benzocoumarin‐Sesamol conjugates using absorption, steady‐state fluorescence emission, and time‐resolved emission measurements. The structural characterization of the synthesized dyes was carried out using FT‐IR, 1H‐NMR, 13C‐NMR, and MS. The ground state dipole moment of both the molecules in the gaseous phase is estimated from ab initio computations by using Gaussian 09W software and also from solvatochromic method and the results are compared. Stoke's shift exhibits a redshift with an increase in solvent polarity for synthesized indicating a π–π* transition. The HOMO‐LUMO energy gaps computed from density functional theory and absorption threshold wavelengths are found to be in good agreement with each other. The Global chemical reactivity descriptor parameter and electrostatic potential (MESP) plots suggest that molecules have strong electrophilic and nucleophilic sites. The preliminary photophysical observations and results suggest that the fluorescent dyes can be considered as potential material for the construction of solar cells, fluorescent probes, and chemosensors.

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“…The determination of HOMO-LUMO energies also helps in understanding the chemical stability of a molecule in terms of a parameter known as chemical hardness (η). The molecules possessing large HOMO-LUMO energy gap are considered as hard, whereas moleculespossessing small HOMOLUMO energy gaps are considered as soft molecules [31][32].…”

Section: Computational Analysismentioning

confidence: 99%

Effect of D-π-A substituted Bromomethylcoumarin Derivatives on Optoelectronic Properties: Experimental and Computational Studies

Madar¹,

Pujar

Shridhar³

et al. 2022

Preprint

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Here we report a simple method for the synthesis of a D−π−A substituted bromomethyl coumarin derivatives 1-(6-Bromo-benzo[1, 3]dioxol-5-yloxymethyl)-benzo[f]chromen-3-one (1BDYMBC) and 4-(6-Bromo-benzo[1, 3]dioxol-5-yloxymethyl)-benzo[h]chromen-2-one (4BDYMBC) via a one-pot chemical reaction. The FT-IR, 1H-NMR, and MS results confirmed the corresponding structure of the synthesized dyes. The substitution effect, on optoelectronic properties was verified using experimental and theoretical techniques. The absorption and fluorescence spectra of fluorescent dyes were recorded in different solvents of different polarity. Stoke's shift exhibits a redshift with an increase in solvent polarity for all molecules indicating a π−π∗ transition. The ground state dipole moments of all fluorescent dyes are estimated theoretically from ab initio computations (integral equation formalism of polarizable continuum model) and experimentally from the solvatochromic method and the results are compared. The excited state dipole moments are estimated using solvatochromic correlations equation and results show that the excited state dipole moments are higher than the ground state dipole moments which suggests that, all fluorescent dyes are more polar in the excited state. The HOMO-LUMO energy gaps computed from density functional theory and absorption threshold wavelengths are found to be in good agreement with each other and also support intramolecular charge transfer (ICT). The chemical hardness of the molecules is determined and the chemical stability is discussed. Further, using DFT molecular electrostatic potential (MESP) plots, the electrophilic site and nucleophilic site which are useful in photochemical reactions were identified. Finally, all the preliminary observations and results suggest that the fluorescent dyes can be considered as potential candidates for fluorescent probes and for the construction of dye sensitized solar cell in future.

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Synthesis and photophysical properties of a novel phthalimide derivative using solvatochromic shift method for the estimation of ground and singlet excited state dipole moments

Cited by 31 publications

References 31 publications

Studies on Photophysical Properties of Mono-carbonyl Curcumin Analogues: Experimental and Theoretical approach

Studies on Photophysical Properties of Mono-carbonyl Curcumin Analogues: Experimental and Theoretical approach

Designing Highly Fluorescent BenzoCoumarin‐Sesamol Conjugates for Optoelectronic Applications

Effect of D-π-A substituted Bromomethylcoumarin Derivatives on Optoelectronic Properties: Experimental and Computational Studies

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