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

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

Anna Kolbus et al. J Fluoresc. 2019 Nov.

Abstract

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.

Keywords: Binary solvent mixture; Derivative of coumarin; Fluorescence study; Quantum yield.

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Figures

Scheme 1
Scheme 1

a diethyl malonate/piperidine and next HCl; b DMF/POCl3; c toluene/NaH/100 °C/24 h; d ethanol/piperidine (cat) /boiling/2 h.

Fig. 1
Fig. 1

Optimized chemical structure of NOSQ obtained by DFT calculation in Scigress program (a). Particular atoms have been marked with colors: carbon – dark grey, hydrogen – white, nitrogen – light grey, oxygen – red and sulfur – yellow. On the right (b), the electron density is shown. Red indicates the highest electronegativity and blue indicates positive values of potential

Fig. 2
Fig. 2

Absorption spectra of NOSQ in binary mixture for different content of water and methanol. For solid lines, the arrow shows the water volume percentage increase in the system

Fig. 3
Fig. 3

Fluorescence spectra of NOSQ in binary mixture for different content of water and methanol. For solid lines, the arrow shows the water volume percentage increase in the system

Fig. 4
Fig. 4

The solvent polarity dependence on Stokes shifts, quantum yield and fluorescence lifetimes

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