Synthesis, Characterization and Photophysical Properties of ESIPT Reactive Triazine Derivatives

Four new reactive fluorescent triazine derivatives were obtained from nucleophilic aromatic substitution of cyanuric chloride. The compounds were characterized by infrared spectroscopy (IR), nuclear magnetic resonance (C-13 and H-1 NMR) and high resolution mass spectrometry (HRMS MALDI). UV-Vis and steady-state fluorescence (in solution and in solid state) spectroscopies were also applied to characterize the photophysical behavior. The dyes are fluorescent by an intramolecular proton transfer mechanism (ESIPT) in the blue-orange region, with a large Stokes shift between 6365-10290 cm(-1). The fluorescent cyanuric derivatives could successfully react with cellulose fibers to give new fluorescent cellulosic materials.