Dual Fluorescence and Solvatochromic Study on 3-Acyl Coumarins

Samundeeswari, S.; Kulkarni, Manohar V.; Yenagi, Jayashree; Tonannavar, J.

doi:10.1007/s10895-017-2052-z

Cited by 15 publications

(11 citation statements)

References 44 publications

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“…TSF was synthesized according to method 2, namely the classical H 2 SO 4 catalyzed route involving the use of thiosemicarbazide and appropriate 5-sulfosalicylic acid as the substrate (Scheme 2) [38,39].…”

Section: Methodsmentioning

confidence: 99%

“…In method 1, the effect of polarization dependence and hydrogen bonding effects with solvents can be expressed by the function ETN which was first proposed by Reichardt [28,38,39]. A normalized E T (30) value, specifically the microscopic solvent polarity (ETN) is useful in measuring solvent polarity by solvatochromic methods using betaine dye as a probe solute.…”

Section: Methodsmentioning

confidence: 99%

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Non-Typical Fluorescence Effects and Biological Activity in Selected 1,3,4-thiadiazole Derivatives: Spectroscopic and Theoretical Studies on Substituent, Molecular Aggregation, and pH Effects

Budziak

Karcz

Makowski

et al. 2019

IJMS

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The below article presents the results of spectroscopic research, theoretical (time-dependent density functional theory (TD-DFT)), microbiological, and antioxidative calculations for three compounds from the group of 1,3,4-thiadiazoles: 2-amino-5-phenyl-1,3,4-thiadiazole (TB), 2-amino-5-(2-hydroxyphenyl)-1,3,4-thiadiazole (TS), 2-amino-5-(2-hydroxy-5-sulfobenzoyl)-1,3,4-thiadiazole (TSF). In the fluorescence emission spectra (TS) of solutions with varying concentrations of hydrogen ions, a particularly interesting effect of dual fluorescence was observed. The aforementioned effect was observed even more clearly in the environment of butan-1-ol, relative to the compound’s concentration. Depending on the modification of the resorcylic substituent (TS and TSF), we observed the emergence of two separate, partially overlapping, fluorescence emission spectra or a single emission spectrum. Interpretation of the obtained spectra using stationary and time-resolved spectroscopy allowed the correlation of the effect’s emergence with the phenomenon of molecular aggregation (of a particular type) as well as, above all, the structure of the substituent system. The overlap of said effects most likely induces the processes related to the phenomenon of charge transfer (in TS) and is responsible for the observed fluorescence effects. Also, the position of the –OH group (in the resorcylic ring) is significant and can facilitate the charge transfer (CT). The determinations of the changes in the dipole moment and TD-DFT calculations further corroborate the above assumption. The following paper presents the analysis (the first for this particular group of analogues) of the fluorescence effects relative to the changes in the structure of the resorcylic group combined with pH effects. The results of biological studies also indicate the highest pharmacological potential of the analogue in the case where the effects of dual fluorescence emission are observed, which predisposes this particular group of fluorophores as effective fluorescence probes or potential pharmaceuticals with antimycotic properties.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Non-Typical Fluorescence Effects and Biological Activity in Selected 1,3,4-thiadiazole Derivatives: Spectroscopic and Theoretical Studies on Substituent, Molecular Aggregation, and pH Effects

Budziak

Karcz

Makowski

et al. 2019

IJMS

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“…Method 1. Based on the papers by Bakshiev and Kawski-Chamma-Viallet [44], the change in the dipole moment can be calculated from the following two Eqs (4 and 5):…”

Section: Time-correlated Single Photon Counting (Tcspc)mentioning

confidence: 99%

Spectroscopic and theoretical studies of fluorescence effects induced by the ESIPT process in a new derivative 2-Hydroxy-N-(2-phenylethyl)benzamide – Study on the effects of pH and medium polarity changes

et al. 2020

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The paper presents the results of studies conducted with the use of stationary and timeresolved fluorescence spectroscopy for the new derivative 2-Hydroxy-N-(2-phenylethyl) benzamide (SAL-3) in aqueous solutions with various concentrations of hydrogen ions as well as in solvent mixtures (i.e. media with changing polarity/polarizability). For the compound selected for the study placed in aqueous solutions with varying concentrations of hydrogen ions, the fluorescence emission spectra revealed a single emission band within most of the pH range, however, at low pH (pH<3) a significant broadening (noticeable effect of dual fluorescence) and shifting of the band was observed. Whereas, for water and polar (protic) solvents, we observed a very interesting phenomenon of dual fluorescence never before reported for this particular group of analogues (with the specific substituent system). Based on the results of the experiments, it was observed that the presented effects may be related both with conformational effects (related to the possible positioning of the-OH group on the side of the carbonyl system, which facilitates the possibility of proton transfer) as well as, most importantly, the effects of excited state intramolecular proton transfer (ESIPT-Excited State Intramolecular Proton Transfer) related in this case with the necessary (new/ previously unobserved in published literature) presence of ionic and non-ionic forms of the compound). Both the conducted quantum-mechanical [TD]DFT-Time-Dependent Density Functional Theory) calculations and excited state dipole moment change calculations for

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“…Solvent polarity and the local environment both suppress the emission intensity and shift the spectra (Figure ), the latter of which is one of the earliest observations in fluorescence . The increase of solvent polarity increases red shift of fluorescence maxima band.…”

Section: Uncertaintymentioning

confidence: 99%

Experimental methods in chemical engineering: Fluorescence emission spectroscopy

et al. 2019

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Fluorescence is a luminescence phenomenon in which a compound emits light after absorption of electromagnetic irradiation. Specialized terms such as photoluminescence, cathodoluminescence, anodoluminescence, radioluminescence, and x-ray fluorescence sometimes are used to indicate the type of exciting radiation. Fluorescence spectroscopy provides reliable quantitative and qualitative data. It precisely tracks chemical reactions from fluorescent materials compounds with aromatic groups, or conjugated planar, or cyclic molecules. It is up to 1000 times more sensitive than UV-vis or infrared spectroscopy. Fluorescence intensity depends on the fluorophore (compound that fluoresces), its concentration, excitation and emission wavelengths, temperature and contamination. We adjust the slit dimensions, photomultiplier tube voltage and bandpass filter cutoff to maximize the signal while avoiding saturating the detector. Together with x-ray diffraction, it is the most common spectroscopic technique with applications in geology, chemistry, medicine, and astronomy. A bibliometric analysis of the top 10 000 cited papers identified 5 clusters based on keywords centered around: (1) cancer, cells, and proteins;(2) aggregation induced emission, LED, and complexes; (3) live cells, sensors, and probes; (4) quantum dots, DNA, and biosensors; and (5) nanoparticles, in vivo, and drug delivery. Chemical engineers have yet to fully embrace fluorescence spectroscopy as the category is ranked 16th among all scientific categories that exploit it.

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Dual Fluorescence and Solvatochromic Study on 3-Acyl Coumarins

Cited by 15 publications

References 44 publications

Non-Typical Fluorescence Effects and Biological Activity in Selected 1,3,4-thiadiazole Derivatives: Spectroscopic and Theoretical Studies on Substituent, Molecular Aggregation, and pH Effects

Non-Typical Fluorescence Effects and Biological Activity in Selected 1,3,4-thiadiazole Derivatives: Spectroscopic and Theoretical Studies on Substituent, Molecular Aggregation, and pH Effects

Spectroscopic and theoretical studies of fluorescence effects induced by the ESIPT process in a new derivative 2-Hydroxy-N-(2-phenylethyl)benzamide – Study on the effects of pH and medium polarity changes

Experimental methods in chemical engineering: Fluorescence emission spectroscopy

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