Open AccessBenzo[de]naphtho[1,8-gh]quinolines: synthesis, photophysical studies and nitro explosives detection
Author(s) -
Igor L. Nikonov,
Igor А. Khalymbadzha,
Leila К. Sadieva,
Мaria I. Savchuk,
Еkaterina S. Starnovskaya,
Dmitry S. Kopchuk,
Igor S. Коvalev,
Grigory А. Кim,
О. Н. Чупахин
Publication year - 2021
Publication title -
chimica techno acta
Language(s) - English
Resource type - Journals
eISSN - 2411-1414
pISSN - 2409-5613
DOI - 10.15826/chimtech.2021.8.4.15
Subject(s) - chemistry , fluorescence , quantum yield , nitro , intramolecular force , homo/lumo , titration , yield (engineering) , photochemistry , explosive material , medicinal chemistry , stereochemistry , molecule , organic chemistry , materials science , alkyl , physics , quantum mechanics , metallurgy
A rational synthetic approach to substituted naphtho[1,8-gh]quinolines using intramolecular cyclization in the presence of potassium in the series of (naphthalen-1-yl)isoquinolines is described. The photophysical properties of the obtained compounds were studied; in particular, fluorescence emission was detected in the range 454 - 482 nm with a quantum yield of up to 54%. We also calculated the HOMO-LUMO energies and optimized molecular structures for the resulting fluorophores. Based on the results of fluorescence titration, the Stern-Volmer constants (up to 21587 M-1) and the detection limits of nitroanalytes (up to 1.4 ppm) were calculated, confirming the possibility of their use as potential chemosensors for the visual detection of nitro-containing explosives.
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