Synthesis, absorption and fluorescence properties of N-triazinyl derivatives of 2-aminoanthracene

N-(4,6-dichloro-1,3,5-triazin-2-yl)-2-aminoanthracene was synthesized by substitution of one chlorine atom of 2,4,6-trichloro-1,3,5-triazine with 2-aminoanthracene. A new series of N-triazinyl-2-aminoanthracenes was prepared by nucleophilic substitution of one or both chlorine atoms on N-(4,6-dichloro-1,3,5-triazin-2-yl)-2-aminoanthracene with electron-donating methoxy or phenylamino groups. The UV/Vis absorption, fluorescence and excitation spectra as well as the fluorescence quantum yields of the prepared compounds were measured in 1,4-dioxane, ethyl acetate, dibutyl ether and acetonitrile; nanosecond kinetics of the fluorescence decay was measured in different solvents. The influence of the character of the substituent on triazinyl ring and of the solvent polarity upon the absorption and fluorescence spectra and fluorescence quantum yields are discussed.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► N-triazinyl-2-aminoanthracenes were prepared and characterized. ► Relationships structure-UV/Vis absorption and fluorescence spectra were studied. ► Chlorine atoms on triazinyl ring and solvent polarity decrease the qF. ► The fluorescence quenching is caused by the CT states in deactivation cascade.