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  • Acridine-based fluorophores...
    Baig Moghal, Zubair Khalid; Manivannan, Ramalingam; Son, Young-A

    Dyes and pigments, January 2022, 2022-01-00, Letnik: 197
    Journal Article

    9-arylated acridine-based derivatives (AUPAO &AUEA) with high visibility, fluorescence, and excellent lightfastness were synthesized in good yield. The molecules were characterized by 1H NMR, 13C NMR, HRMS and further investigated for photophysical properties. Initially, absorption and emission studies were carried out in wide-ranging polarity solvents to choose a solvent of interest for further investigations. Concentration-dependent studies were carried out in ethanol to determine an optimized concentration to study lightfastness studies. These molecules showed excellent lightfastness properties in solution form when compared to commercially available acridine orange. pH-dependent studies were also carried out to observe the behavior of cationic dyes in a wide range of pH to optimize pH for dyeing. The presence of extended conjugation at the 9th position and additional four methoxy groups resulted in highly fluorescent dyes with excellent quantum yield. The steric interactions, higher twist, and unrestricted rotation of the conjugation pathway between the aromatic ring at the 9th position and the acridine core decreased the transition probability and energy transfer that helped improve the lightfastness. The introduction of a hydroxyl group in AUEA increased the solubility and helped in controlled dispersion while dyeing. Further, they were dyed on modacrylic fabric as high visibility fluorophores, and later the color coordinates, color strengths were measured. •9-arylated acridine-based high visible fluorophores (AUPAO &AUEA) were synthesized in good yields.•These molecules showed a high molar absorption coefficient and fluorescence with more quantum yield.•These molecules are promising candidates with improved lightfastness when compared to acridine orange (AO).•The presence of aromatic ring at 9th position and four methoxy groups helped in increased fluorescence and quantum yield.•The presence of the hydroxyl group gave AUEA an advantage over AUPAO in solubility and diverse pH conditions.•These molecules also demonstrated good dyeing properties on modacrylic fibers.