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Description
Quinacridones are a class of fluorescent compounds sharing an aromatic structural motif, and as such, they can be employed as fluorophores when using both visual and instrumental techniques, especially for the research of biomolecules (DNA, RNA, saccharides, etc.). These compounds have a special advantage over other fluorophores, as they provide a solution to the problem posed by the autofluorescence of biomolecules in the blue area of the electromagnetic spectrum. This can cause interference if techniques relying on blue-emitting fluorophores are used. Namely, this problem can generally be solved using higher wavelength emitting fluorophores, a criterion for which these compounds are a good match.
This study offers a relatively fast and simple synthetic method, involving derivatization of the starting material (basic structural motif of the desired compound) by simplifying the variation of the derivatives’ substituents. Diethyl succinate is used as a starting material, while the specific derivatives are obtained by reacting diethyl succinylo succinate with an appropriate arylamine. The synthetic steps were optimized, and the reaction was monitored by TLC. The derivatives are characterized using UV-VIS spectroscopy, powder XRD, vibrational spectroscopy (IR and Raman), and NMR. The fluorescence of the compounds is observed under UV light.
Twenty-three novel fluorescent compounds were synthesized, and several trends were observed. A correlation between optoelectronic properties and the electron donating or withdrawing effect of the substituents was identified and analysed. The effect of hydrogen bonding and extended aromatic systems was also studied.
