Squaramides for colorimetric and fluorescent anion sensing.

Autor: Lane JDE; School of Chemistry, The University of Sydney, NSW, 2006, Australia. kate.jolliffe@sydney.edu.au., Jolliffe KA; School of Chemistry, The University of Sydney, NSW, 2006, Australia. kate.jolliffe@sydney.edu.au.; Australian Research Council Centre of Excellence for Innovations in Peptide and Protein Science, The University of Sydney, 2006, NSW, Australia.; The University of Sydney Nano Institute (Sydney Nano), The University of Sydney, NSW 2006, Australia.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2023 Apr 12; Vol. 21 (15), pp. 3226-3234. Date of Electronic Publication: 2023 Apr 12.
DOI: 10.1039/d3ob00069a
Abstrakt: A series of fluorophore-containing squaramides were synthesised to investigate the fluorescent and colorimetric response to anions of squaramides containing large aromatic substituents. Squaramides in which the fluorophores were conjugated directed to the squaramide motif were found to have highly acidic NH protons, giving rise to complicated fluorescence behaviour and colour changes upon addition of anions. In contrast, squaramides incorporating a methylene spacer to electronically insulate the fluorophore from the squaramide gave a relatively simple fluorescence response upon addition of anions, which was attributed to a decrease in excimer emission relative to monomer emission intensity, likely due to a disaggregation mechanism. The ratio of excimer : monomer emission was used to provide a ratiometric fluorescent response to anions, with the most selective molecules demonstrating a preference for binding to sulfate over other anions.
Databáze: MEDLINE