Novel anthraquinone α-aryl-α-aminophosphonates: Synthesis, spectroscopy and imaging by confocal laser scanning microscopy of trematode Opisthioglyphe ranae

A small library of new anthraquinone α-aryl-α-aminophosphonates with N-C-P molecular fragment was synthesized under Kabachnik-Fields one-pot solvent-free reaction conditions from 1-aminoanthraquinone. 1H-, 13C-, 31P NMR and FTIR spectroscopy and high-resolution accurate mass measurement was employed to confirm structures of new dyes. The photophysical parameters of the studied α-aminophosphonates have been investigated by means of UV–Vis and fluorescence spectroscopy in organic solvents of varying polarity. Obtained compounds were found to emit light from 586 nm (EtOAc) to 620 nm (DMSO) with fluorescence bathochromic shifts reaching up to 30 nm, Stokes shift of 4573 cm– 1 and photostability of up to 60 % of initial intensity upon photofading for 4 h. α-Aryl-α-aminophosphonate was used for the first time as a dye for rapid bioimaging of trematode Opisthioglyphe ranae in confocal laser scanning microscopy.