Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Fluorinated 2,3-diaminophenazines: synthesis, mechanism of formation, and properties. / Li, Jiayao; Krasnov, Vyacheslav; Karpova, Elena и др.
в: New Journal of Chemistry, Том 47, № 42, 29.09.2023, стр. 19556-19568.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Fluorinated 2,3-diaminophenazines: synthesis, mechanism of formation, and properties
AU - Li, Jiayao
AU - Krasnov, Vyacheslav
AU - Karpova, Elena
AU - Andreev, Rodion
AU - Genaev, Alexandr
AU - Rumyantseva, Elizabeth
AU - Shundrina, Inna
AU - Romanov, Vasily
AU - Selivanova, Galina
N1 - The investigation was carried out with the financial support of the Ministry of Education and Science of the Russian Federation (Project FWUE-2022-0002). Jiayao Li thanks the China Scholarship Council for financial support. Authors would like to acknowledge the Multi-Access Chemical Research Center SB RAS for spectral and analytical measurements. Публикация для корректировки.
PY - 2023/9/29
Y1 - 2023/9/29
N2 - A series of new fluorinated 2,3-diaminophenazines were obtained by the oxidation of fluorinated o-phenylenediamines with iron trichloride in water acidified with HCl. Isomeric 2,3-diaminophenazines with F atoms in both benzene fragments were obtained when o-phenylenediamines contained an F atom at the ortho-position with respect to the amino group. The ratio of isomers depends on the number and position of F atoms in o-phenylenediamines. DFT calculations for the formation of fluorinated 2,3-diaminophenazines in question were consistent with the experimentally observed ratio of the isomers. The formation of the predominant isomer was attributed to the action of the amino group with the highest N-charge of protonated o-phenylenediamines at the most electron-depleted position of the most stable protonated diimine. New compounds were characterized using various spectroscopy techniques (IR, UV, 1H, 19F, 13C NMR, and mass). Fluorinated 2,3-diaminophenazines are heat-resistant and fluoresce from green to red depending on the number of F atoms in the ring bearing amino groups. The presence of F atoms decreases the emission intensity but at the same time bathochromically shifts the fluorescence maximum. In the absence of the F atom in the ring bearing amino groups, fluorinated 2,3-diaminophenazines exhibited fluorescence intensities comparable to those of a non-fluorinated analog.
AB - A series of new fluorinated 2,3-diaminophenazines were obtained by the oxidation of fluorinated o-phenylenediamines with iron trichloride in water acidified with HCl. Isomeric 2,3-diaminophenazines with F atoms in both benzene fragments were obtained when o-phenylenediamines contained an F atom at the ortho-position with respect to the amino group. The ratio of isomers depends on the number and position of F atoms in o-phenylenediamines. DFT calculations for the formation of fluorinated 2,3-diaminophenazines in question were consistent with the experimentally observed ratio of the isomers. The formation of the predominant isomer was attributed to the action of the amino group with the highest N-charge of protonated o-phenylenediamines at the most electron-depleted position of the most stable protonated diimine. New compounds were characterized using various spectroscopy techniques (IR, UV, 1H, 19F, 13C NMR, and mass). Fluorinated 2,3-diaminophenazines are heat-resistant and fluoresce from green to red depending on the number of F atoms in the ring bearing amino groups. The presence of F atoms decreases the emission intensity but at the same time bathochromically shifts the fluorescence maximum. In the absence of the F atom in the ring bearing amino groups, fluorinated 2,3-diaminophenazines exhibited fluorescence intensities comparable to those of a non-fluorinated analog.
UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85174406861&origin=inward&txGid=32bc9d639ff3e94d9ed874bc0bbb82e8
UR - https://www.mendeley.com/catalogue/55b7ac76-5da1-3309-b0b1-08c769bc4711/
U2 - 10.1039/d3nj02875e
DO - 10.1039/d3nj02875e
M3 - Article
VL - 47
SP - 19556
EP - 19568
JO - New Journal of Chemistry
JF - New Journal of Chemistry
SN - 1144-0546
IS - 42
ER -
ID: 59554268