Spectroscopic and theoretical studies of dual fluorescence in 2-hydroxy-n-(2-phenylethyl)benzamide induced by ESIPT process – Solvent effects

Niemczynowicz, Agnieszka; Czernel, Grzegorz; Matwijczuk, Arkadiusz; Makowski, Marcin; Pustuła, Katarzyna; Karcz, Dariusz; Matwijczuk, Alicja; Górecki, Andrzej; Piotrowicz-Cieślak, Agnieszka I.

doi:10.1016/j.jlumin.2018.12.024

Cited by 12 publications

(2 citation statements)

References 68 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This is a typical characteristic of the tautomer emission. 44,62,63 Like in ether and acetonitrile, two different fluorescence lifetimes were obtained for DHP in 2-propanol, 1-propanol, and 1-butanol (Table 2). Similar to that in aprotic solvents, the relative amplitude of the shorter decay increases at longer wavelengths and that of the longer decay decreases at longer wavelengths in these three solvents.…”

Section: Resultsmentioning

confidence: 99%

Light-Driven Switching between Intramolecular Proton-Transfer and Charge-Transfer States

2021

View full text Add to dashboard Cite

A molecular photoswitch, 2-(4′-diethylamino-2′-hydroxyphenyl)-1Himidazo-[4,5-b]pyridine (DHP), with mutually independent paths of excited-state intramolecular proton transfer (ESIPT) and twisted intramolecular charge transfer (TICT) was developed. Control over these processes was attained by switching the solvents. Depending on the solvent's hydrogen-bond capacity and polarity, either one of the photoprocesses (ESIPT or TICT) or both can be triggered. Accordingly, normal and tautomer emissions, normal and TICT emissions, or triple emission of normal, tautomer, and TICT were obtained from the molecule. The emissions were resolved by fluorescence lifetime. The conclusions were established by synthesizing and studying the methoxy derivative of the molecule.

show abstract

Section: Resultsmentioning

confidence: 99%

Light-Driven Switching between Intramolecular Proton-Transfer and Charge-Transfer States

2021

View full text Add to dashboard Cite

show abstract

“…These compounds show a wide spectrum of pharmacological properties, including neuroprotective [ 6 , 7 ], anti-cancer [ 8 ], antibacterial [ 9 ], antioxidative [ 10 , 11 ], and antimycotic [ 12 , 13 ] effects. Contemporary researchers working in the fields of biophysics and photophysics or photochemistry and utilizing the methods of molecular spectroscopy are faced with the extremely difficult task, posed by medical and pharmaceutical sciences, of determining the molecular properties of continuously developed new compounds [ 1 , 2 , 14 , 15 , 16 , 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

ESIPT-Related Origin of Dual Fluorescence in the Selected Model 1,3,4-Thiadiazole Derivatives

et al. 2020

Self Cite

View full text Add to dashboard Cite

In our previous work, we discussed the emergence of the dual fluorescence phenomenon in selected compounds from the group of 1,3,4-thiadiazoles. The results obtained in a number of experimental studies, supported by [TD]DFT calculations, clearly indicated that the phenomenon of dual fluorescence stemmed from an overlap of several factors, including the correct conformation of the analyzed molecule and, very significantly in this context, aggregation effects. Where those two conditions were met, we could observe the phenomenon of intermolecular charge transfer (CT) and the emergence of electronic states responsible for long wave emissions. However, in light of the new studies presented in this paper, we were able, for the first time, to provide a specific theory for the effect of dual fluorescence observed in the analyzed group of 1,3,4-thiadiazoles. We present the results of spectroscopic measurements conducted for two selected analogues from the 1,3,4-thiadiazole group, both in polar and non-polar solvents, which clearly evidence (as we have already suspected in the past, albeit have not shown in publications to date) the possibility of processes related to emission from the tautomer formed in the process of excited state intramolecular proton transfer, which is responsible for the long-wavelength emissions observed in the selected analogues. The presented results obtained with the use of UV-Vis, fluorescence (stationary and time-resolved), FTIR, and Raman spectroscopy, as well as from calculations of dipole moment changes between the ground and excited state with the use of two derivatives with different structures of the resorcylic system, corroborated our standing hypothesis. At the same time, they excluded the presence of ground state keto forms of the analyzed analogues unless necessitated by the structure of the molecule itself. In this case, aggregation factors enhance the observed effects related to the dual fluorescence of the analyzed compounds (by way of AIE—aggregated induced emissions).

show abstract

Spectral Properties of Highly Emissive Derivative of Coumarin with N,N-Diethylamino, Nitrile and Tiophenecarbonyl Moieties in Water-Methanol Mixture

et al. 2019

View full text Add to dashboard Cite

The new derivative of coumarin (E)-3-[7-(diethyloamino)-2-oxo-chromen-3yl]-2-(tiophene-2-carbonyl)prop-2-enenitrile (NOSQ) was easy synthesized with commercial substrates as a result of the search of new Michael type addition sensors based on coumarins. Spectral properties of highly emissive NOSQ were investigated by steady state analysis (absorption and fluorescence measurements) and time-resolved analysis (fluorescence lifetime measurements). The effect of water-methanol mixture on the photophysical properties of the NOSQ molecule was analyzed. With increasing of volumetric fraction of water the intensity of absorbance and fluorescence was strongly reduced. The NOSQ quantum yield in methanol was quite high and the first portions of water caused a significant increase in this value. Water, which is usually a quencher, in this case caused the increase in the quantum yield. The fluorescence lifetimes had second-order decay and the values of fluorescence lifetime increased with increasing alcohol content. Density functional theory (DFT) calculations and experimental data remained in agreement and showed that the interaction between the NOSQ molecule and the solvent affects the appearance of the new conformer.

show abstract

Spectroscopic and theoretical studies of dual fluorescence in 2-hydroxy-n-(2-phenylethyl)benzamide induced by ESIPT process – Solvent effects

Cited by 12 publications

References 68 publications

Light-Driven Switching between Intramolecular Proton-Transfer and Charge-Transfer States

Light-Driven Switching between Intramolecular Proton-Transfer and Charge-Transfer States

ESIPT-Related Origin of Dual Fluorescence in the Selected Model 1,3,4-Thiadiazole Derivatives

Spectral Properties of Highly Emissive Derivative of Coumarin with N,N-Diethylamino, Nitrile and Tiophenecarbonyl Moieties in Water-Methanol Mixture

Contact Info

Product

Resources

About