Potential chiral fluorescent molecular probes based on an α,β-unsaturated ketone for anion detection

Abstract

A series of potential chiral compounds containing an α,β-unsaturated ketone was developed for anion detection. The interplay of compounds and biological momentous anions (Cl−, H2PO4−, I−, AcO−, HS−, F−, and Br−) was evaluated by UV-vis experiments, fluorescence experiments, and electrochemical tests. By comparison, compound 1 had the best selectivity and compound 5 had the strongest binding ability among the five compounds. And compound 5 had the highest sensitivity to H2PO4− among the measured anions, and it also can be applied to actual samples, the content of H2PO4− tested in the potassium dihydrogen phosphate fertilizer solution reached above 97.5% of the marked content, and the recovery rates were within the range of 98.5–99.1%, attesting that this method was reliable for the test of H2PO4− in fertilizer. Through HRMS titration, circular dichroism and optical rotation experiments, the probable interacted mechanism was proved that the interaction site was the C=C of the α,β-unsaturated ketone structure. In addition, the interacted mechanism was researched from the perspective of chirality. Furthermore, theoretical investigation analysis was introduced to reveal that the roles of molecular frontier orbitals in molecular interplay were determined. Therefore, this series of potential chiral compounds has potential application prospects in anion recognition.

Artemisinin: a novel chiral electrochemiluminescence luminophore-assisted enantiospecific recognition and mechanism identification

“…To test the enantiomer selectivity of the system, we measured the ECL strength of the artemisinin-potassium persulfate system when adding l -Cys + d -Cys mixtures with different enantiomer overpass values (ee%). 49,50 The prepared ee value was obtained from the concentration of the enantiomer using the formula ([ l ] − [ d ])/([ l ] + [ d ]) × 100%. Fig.…”

“…To test the enantiomer selectivity of the system, we measured the ECL strength of the artemisinin-potassium persulfate system when adding L-Cys + D-Cys mixtures with different enantiomer overpass values (ee%). 49,50 The prepared ee value was obtained from the concentration of the enantiomer using the formula ( 4E shows a linear relationship between ECL intensity and enantiomer overdose (R 2 = 0.9936), indicating that an ART-based ECL system could be used for enantiomer overdose detection.…”

Bioorthogonal Caging-Group-Free Photoactivatable Probes for Minimal-Linkage-Error Nanoscopy

“…To prepare the acrylamide-linked PaX scaffolds ( 9 – 12 ), new acrylate-functionalized PaX were prepared ( S9 , see Supporting Information for details) and coupled to commercially available tetrazine amines to yield the secondary acrylamide products ( 9 , 10 ). To access the tertiary N -methylacrylamides ( 11 , 12 ), N -methyl-4-(6-methyl-1,2,4,5-tetrazin-3-yl)­benzylamine was additionally synthesized and coupled with the acrylic acids S9 and S14 (see Supporting Information). Much to our surprise, the acrylamide-derived PaX scaffolds showed notably slower photoactivation rates, likely due to the greater electron deficiency of the radical trap.…”