Abstract
Important scientific areas, such as cellular biology, medicine, pharmacy, and environmental sciences, are dependent on very sensitive analytical techniques to track and detect biomolecules. In this work, we develop a simple, low-cost and effective synthetic strategy to produce new red-shifted 4-styrylcoumarin derivatives as promising inexpensive fluorescent labels for biomolecules. The extension of the delocalized π-electron system results in bathochromic shifts in these new coumarin derivatives, which also present large Stokes shifts. In addition, density functional theory and time-dependent density functional theory calculations helped to rationalize the photophysical properties observed by the experimental results.
Highlights
Cellular biology, medicine, pharmacy and environmental sciences require highly sensitive analytical techniques to track and detect nucleic acids, oligonucleotides, antibodies, amino acids, proteins, lipids, carbohydrates, and other biomolecules [1,2,3,4,5,6]
The main synthetic strategy to obtain 4-styrylcoumarin derivatives was based on the high acidity of the methyl protons present at position 4 in 2-(7-(diethylamino)-4-methyl-2Hchromen-2-ylidene)malononitrile (3), which enable aldol condensation reactions
We reasoned that the incorporation of one 4-styryl group containing electron-donating groups (EDGs) or electron-withdrawing groups (EWGs) at the para position could increase the π delocalization and the push−pull character of the chromophore
Summary
Medicine, pharmacy and environmental sciences require highly sensitive analytical techniques to track and detect nucleic acids, oligonucleotides, antibodies, amino acids, proteins, lipids, carbohydrates, and other biomolecules [1,2,3,4,5,6]. The amine-reactive fluorescent labels, since amino groups are either abundant or introduced into biomolecules, are the most frequently used to prepare numerous bioconjugates for direct or indirect immunochemistry, fluorescence in situ hybridization (FISH), histochemistry, cell tracing, receptor binding and other biological applications [20,21,22]. In this context, due to the high cost of the available commercial fluorescent labels, coumarin derivatives can be a solution to develop low-cost new fluorophores with absorption and emission at long wavelengths, combined with large Stokes shifts
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