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Facile synthesis of functionalized urea, imidazolium salt, azide, and triazole from a 2-amino-5,7-dimethyl-1,8-naphthyridine scaffold and their utilization in fluoride ion sensing
Ist Teil von
New journal of chemistry, 2018, Vol.42 (12), p.10059-10066
Ort / Verlag
Cambridge: Royal Society of Chemistry
Erscheinungsjahr
2018
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
Four new 2-amino-5,7-dimethyl-1,8-naphthyridine derivatives (
1–4
) possessing urea, amide-imidazolium salt, amide-azide, or amide-triazole moieties were synthesized in good to excellent yields by derivatization of 2-amino-5,7-dimethyl-1,8-naphthyridine. We examined their anion recognition abilities towards different anions such as fluoride, chloride, bromide, iodide, nitrate, dihydrogen phosphate, cyanide, hexafluorophosphate, perchlorate, hydrogen sulphate and acetate by
1
H NMR and UV-Vis spectroscopy. Among various 2-amino-5,7-dimethyl-1,8-naphthyridine derivatives, only
1a
and
2
showed spectroscopic and colorimetric change when treated with fluoride ions among other anions. The F
−
ions first established a hydrogen-bonding interaction with
1a
to give the most stable 1 : 1 complex and then, after addition of a second equivalent, the F
−
ions induced urea deprotonation due to the formation of HF
2
−
. Moreover,
2
underwent deprotonation of amide –NH proton after the addition of 1 equiv. of fluoride ions. The action of the probes was thoroughly investigated by DFT calculations that also supported the H-bonding induced deprotonation sensing mechanism.