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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

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Abstract

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 1H 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 HF2. 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.

Graphical abstract: 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

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Publication details

The article was received on 29 Jan 2018, accepted on 24 Apr 2018 and first published on 24 Apr 2018


Article type: Paper
DOI: 10.1039/C8NJ00503F
Citation: New J. Chem., 2018, Advance Article
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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

    M. K. Chahal, T. A. Dar and M. Sankar, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ00503F

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