Novel Anthraquinone α-aryl-α-aminophosphonates: Synthesis, Spectroscopy and Imaging by Confocal Laser Scanning Microscopy of Trematode Opisthioglyphe Ranae

Journal of Photochemistry and Photobiology A: Chemistry 2023
Armands Maļeckis, Marija Cvetinska, Evans Griškjāns, Ligita Mežaraupe, Muza Kirjušina, Veronika Pavlova, Jeļena Kirilova

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.

Keywords
Anthraquinone; α-aminophosphonates; Kabachnik-Fields reaction; Fluorescence; Confocal microscopy
DOI
10.1016/j.jphotochem.2023.114918
Hyperlink
https://www.sciencedirect.com/science/article/pii/S1010603023003830?via%3Dihub

Maļeckis, A., Cvetinska, M., Griškjāns, E., Mežaraupe, L., Kirjušina, M., Pavlova, V., Kirilova, J. Novel Anthraquinone α-aryl-α-aminophosphonates: Synthesis, Spectroscopy and Imaging by Confocal Laser Scanning Microscopy of Trematode Opisthioglyphe Ranae. Journal of Photochemistry and Photobiology A: Chemistry, 2023, Vol. 444, Article number 114918. ISSN 1010-6030. Available from: doi:10.1016/j.jphotochem.2023.114918

Publication language
English (en)