The synthesis and optical properties of novel fluorescent iminocoumarins and bis-iminocoumarins: Investigations in the series of urea derivatives

Fakhfakh, Mehdi; Turki, H.; Fery–Forgues, Suzanne; Gharbi, Rachid El

doi:10.1016/j.dyepig.2009.07.003

Cited by 25 publications

(10 citation statements)

References 34 publications

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“…The length of spacer groups plays important role during the binding of fluorescent probes with the biomolecules. The purpose of fused iminocoumarin designing was to achieve the planarity which will enhance electron flow within the conjugated ring system and to avoid intersystem crossing due to free rotation of groups present at 3-position on coumarin unit [25,31].…”

Section: Introductionmentioning

confidence: 99%

Novel Iminocoumarin Derivatives: Synthesis, Spectroscopic and Computational Studies

Chemate

Sekar

2015

J Fluoresc

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Three novel iminocoumarin derivatives with high quantum yield are synthesized from 3-benzimidazole substituted coumarin and different aromatic aldehydes. The photophysical behavior of the synthesized compounds was studied using UV-visible and fluorescence spectroscopy in polar and non-polar solvents. The compounds show absorption maxima at around 450 nm and emission maxima at around 500 nm. The quantum yields of compounds in dichloromethane and chloroform are more than 0.90. The absorption, emission and quantum yield of compounds are dependent on the polarity of solvents. Along with an intense absorption, these compounds show shoulder absorption peak in the studied solvents. The solvent polarity plots revealed the charge transfer process in the synthesized molecules from donor to acceptor. Density Functional Theory and Time Dependent Density Functional Theory computations have been used to have more understanding of the structural, molecular, electronic and photophysical parameters of the dyes. The dyes were characterized by FT-IR, (1)H NMR, (13)C NMR and mass spectral analysis.

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Section: Introductionmentioning

confidence: 99%

Novel Iminocoumarin Derivatives: Synthesis, Spectroscopic and Computational Studies

Chemate

Sekar

2015

J Fluoresc

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“…In the first step (Scheme 1), the 3-cyano-2-iminocoumarins 3 were synthesized from an equimolecular mixture of various substituted 2-hydroxy benzaldehyde 1 (1a: 2-hydroxy-3-methoxybenzaldehyde, 1b: 4-diethylamino-2-hydroxybenzaldehyde, 1c: 2,4-dihydroxybenzaldehyde, 1d: 2-hydroxynaphthaldehyde, 1e: 2-hydroxybenzaldehyde, 1f: 2-hydroxy-4-methoxybnezaldehyde, 1g: 5-bromo-2-hydroxybenzaldehyde, 1h: 3-ethoxy-2-hydroxybenzaldehyde) and propanedinitrile 2 in ethanol with 0.5% of piperidine at room temperature. After a reaction time of 8 -9 hours and elimination of volatile compounds in vacuo, the 3-cyano-2-iminocoumarins 3 were prepared easily according to this classical protocol previously developed in our laboratory [18] [19] [20].…”

Section: Synthesis and Characterizationsmentioning

confidence: 99%

3-(Tetrazol-5-yl)-2-imino-coumarins Derivatives: Synthesis, Characterization, and Evaluation on Tumor Cell Lines

Bouattour¹,

Fakhfakh²,

El-Gharbi³

et al. 2021

IJOC

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The first report of new 3-(tetrazol-5-yl)-2-iminocoumarin derivatives is described. The title compounds were prepared in two steps and were obtained in good yields (55-93%). They have been fully characterized by 1 H, 13 C NMR, FTIR, UV-Visible and HRMS. They were tested for their antiproliferative activities against six representative human tumor cell lines (Huh 7-D12, Caco2, MDA-MB231, HCT 116, PC3 and NCI-H727) and HaCat keratinocytes. Among them, compound 5e was active on HCT 116 (IC 50 15 μM).

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“…[ 7 ] It is well known that coumarin derivatives incorporating an electron‐donating group in the 7‐position and an electron‐withdrawing group in the 3‐position of coumarin leads to well absorption and strong fluorescence. [ 8 ] Some probes utilized 7‐(diethylamino)‐3‐[( R ‐imino)methyl]‐2 H ‐chromen‐2‐one as skeleton had been explored as excellent colorimetric chemosensors. [ 9 ] In recent years, boronic acid‐based receptors have attracted considerable interests due to their favorable physicochemical properties and reduced toxicity under physiological conditions.…”

Section: Introductionmentioning

confidence: 99%

A Coumarin‐boronic Based Fluorescent “ON‐OFF” Probe for Hg²⁺ in Aqueous Solution

Lin

Zhang

Yan

et al. 2020

Zeitschrift anorg allge chemie

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In this work, we reported a simple coumarin-boronic acid ester fluorescent probe 1, which displayed very high "ON-OFF" fluorescence response for Hg 2+ in an aqueous environment (H 2 O/CH 3 CN = 1:1, v/v) or in a PBS solution (pH = 7.4). With the addition of Hg 2+ to the solution of probe, a color change from light yellow to orange could be observed by naked eye. The detection limits were lower than Scheme 1. The synthesis procedure of probe 1.

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The synthesis and optical properties of novel fluorescent iminocoumarins and bis-iminocoumarins: Investigations in the series of urea derivatives

Cited by 25 publications

References 34 publications

Novel Iminocoumarin Derivatives: Synthesis, Spectroscopic and Computational Studies

Novel Iminocoumarin Derivatives: Synthesis, Spectroscopic and Computational Studies

3-(Tetrazol-5-yl)-2-imino-coumarins Derivatives: Synthesis, Characterization, and Evaluation on Tumor Cell Lines

A Coumarin‐boronic Based Fluorescent “ON‐OFF” Probe for Hg²⁺ in Aqueous Solution

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The synthesis and optical properties of novel fluorescent iminocoumarins and bis-iminocoumarins: Investigations in the series of urea derivatives

Cited by 25 publications

References 34 publications

Novel Iminocoumarin Derivatives: Synthesis, Spectroscopic and Computational Studies

Novel Iminocoumarin Derivatives: Synthesis, Spectroscopic and Computational Studies

3-(Tetrazol-5-yl)-2-imino-coumarins Derivatives: Synthesis, Characterization, and Evaluation on Tumor Cell Lines

A Coumarin‐boronic Based Fluorescent “ON‐OFF” Probe for Hg2+ in Aqueous Solution

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A Coumarin‐boronic Based Fluorescent “ON‐OFF” Probe for Hg²⁺ in Aqueous Solution