A ratiometric fluorescence chemosensor based on a coumarin–pyrazolone hybrid: the synthesis and an investigation of the photophysical, tautomeric and anion binding properties by spectroscopic techniques and DFT calculations

Babür, Banu; Seferoğlu, Nurgül; Seferoğlu, Zeynel

doi:10.1016/j.tetlet.2015.03.014

Cited by 30 publications

(7 citation statements)

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“…This coordination is usually followed by deprotonation. As shown in Figure , compounds 62 – 71 − can recognize F – due to the presence of coordinating hydroxyl groups, amines or (thio)ureas.…”

Section: Fluorescent Chemosensors Based On Coumarin Platform For Anionsmentioning

confidence: 99%

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Coumarin-Based Small-Molecule Fluorescent Chemosensors

et al. 2019

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Coumarins are a very large family of compounds containing the unique 2H-chromen-2-one motif, as it is known according to IUPAC nomenclature. Coumarin derivatives are widely found in nature, especially in plants and are constituents of several essential oils. Up to now, thousands of coumarin derivatives have been isolated from nature or produced by chemists. More recently, the coumarin platform has been widely adopted in the design of small-molecule fluorescent chemosensors because of its excellent biocompatibility, strong and stable fluorescence emission, and good structural flexibility. This scaffold has found wide applications in the development of fluorescent chemosensors in the fields of molecular recognition, molecular imaging, bioorganic chemistry, analytical chemistry, materials chemistry, as well as in the biology and medical science communities. This review focuses on the important progress of coumarin-based small-molecule fluorescent chemosensors during the period of 2012− 2018. This comprehensive and critical review may facilitate the development of more powerful fluorescent chemosensors for broad and exciting applications in the future.

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Section: Fluorescent Chemosensors Based On Coumarin Platform For Anionsmentioning

confidence: 99%

“…Chemosensors for F – based on coumarin derivatives can be divided to three types: F – promoted cleavage of silicon–oxygen bonds, − hydrogen bond reactions, − and metal ion displacement mechanisms. − …”

Section: Fluorescent Chemosensors Based On Coumarin Platform For Anionsmentioning

confidence: 99%

Coumarin-Based Small-Molecule Fluorescent Chemosensors

et al. 2019

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“… 27 Dyes 13 , 14 , and 15 containing a pyrazolone ring exhibit bathochromically shifted (only by a few nm) absorption and emission spectra ( Table 2 and Figure 3 ) compared to the model compound ( Cum2 ) ( Figure S2 ). 28 Cum2 exhibits a strong hypsochromic shift of the absorption band with increasing solvent polarity and slightly weaker shift in the emission spectra. The extension of the π-framework negligibly redshifts absorption/emission bands of 9 with respect to 3 .…”

Section: Results and Discussionmentioning

confidence: 99%

Polarized Helical Coumarins: [1,5] Sigmatropic Rearrangement and Excited-State Intramolecular Proton Transfer

et al. 2021

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The tandem process of phenol addition to a cyclic α,β-unsaturated ester followed by intramolecular transesterification and [1,5] sigmatropic rearrangement affords a series of helical coumarins based upon a previously unknown 3-amino-7-hydroxybenzo[3,4]cyclohepta[1,2- c ]chromen-6-one core. These novel polarized coumarins, possessing a β-ketoester moiety, have been employed to synthesize more rigid and helical coumarin–pyrazolones, which display green fluorescence. The enhanced emission of coumarin–pyrazolones in polar solvents depends on the nature of the S 1 state. The coumarin–pyrazolones are predicted to have two vertical states close in energy: a weakly absorbing S 1 ( 1 LE) followed by a bright S 2 state ( 1 CT). In polar solvents, the 1 CT can be stabilized below the 1 LE and may become the fluorescent state. Solvatochromism of the fluorescence spectra confirms this theoretical prediction. The presence of an N—H···O=C intramolecular hydrogen bond in these coumarin–pyrazolone hybrids facilitates excited-state intramolecular proton transfer (ESIPT). This process leads to a barrierless conical intersection with the ground electronic state and opens a radiationless deactivation channel effectively competing with fluorescence. Solvent stabilization of the CT state increases the barrier for ESIPT and decreases the efficiency of the nonradiative channel. This results in the observed correlation between solvatochromism and an increase of fluorescence intensity in polar solvents.

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“…As illustrated in Figure , in the absence of Cr 3+ ions, fluorescent spectra of the COPYR probe exhibited a well-built green emission peak at 506 nm upon exciting with a wavelength of 446 nm. The observed emission peak is due to intramolecular charge transfer between coumarin and pyrazole cores . Furthermore, the COPYR receptor was titrated against Cr 3+ ions.…”

Section: Resultsmentioning

confidence: 99%

Highly Sensitive Coumarin–Pyrazolone Probe for the Detection of Cr³⁺ and the Application in Living Cells

et al. 2018

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3-(7-(Diethylamino)-2-oxo-2H-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazol-5(4H)-one (COPYR) was competently synthesized from methyl 3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate and 2-hydrazino-4-phenyl thiazole. The interactions of receptor COPYR with various ions were investigated through absorption and steady-state fluorescence spectral studies, respectively. The results reveal that the complexation of Cr3+ ions with COPYR results in 1:1 stoichiometry, which resulted in a quick color response from fluorescent green to colorless with significant quenching of fluorescence at 506 nm in dimethyl sulfoxide medium. Theoretical calculations (density functional theory) confirm the photophysical changes such as absorbance and emission spectral changes. Furthermore, the confocal imaging of A-549 cells clearly points out that the synthesized probe COPYR could be applied for detecting Cr3+ in living cells.

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A ratiometric fluorescence chemosensor based on a coumarin–pyrazolone hybrid: the synthesis and an investigation of the photophysical, tautomeric and anion binding properties by spectroscopic techniques and DFT calculations

Cited by 30 publications

References 50 publications

Coumarin-Based Small-Molecule Fluorescent Chemosensors

Coumarin-Based Small-Molecule Fluorescent Chemosensors

Polarized Helical Coumarins: [1,5] Sigmatropic Rearrangement and Excited-State Intramolecular Proton Transfer

Highly Sensitive Coumarin–Pyrazolone Probe for the Detection of Cr³⁺ and the Application in Living Cells

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A ratiometric fluorescence chemosensor based on a coumarin–pyrazolone hybrid: the synthesis and an investigation of the photophysical, tautomeric and anion binding properties by spectroscopic techniques and DFT calculations

Cited by 30 publications

References 50 publications

Coumarin-Based Small-Molecule Fluorescent Chemosensors

Coumarin-Based Small-Molecule Fluorescent Chemosensors

Polarized Helical Coumarins: [1,5] Sigmatropic Rearrangement and Excited-State Intramolecular Proton Transfer

Highly Sensitive Coumarin–Pyrazolone Probe for the Detection of Cr3+ and the Application in Living Cells

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Highly Sensitive Coumarin–Pyrazolone Probe for the Detection of Cr³⁺ and the Application in Living Cells