Fluorinated 2,3-diaminophenazines: synthesis, mechanism of formation, and properties Научная публикация
| Журнал |
New Journal of Chemistry
ISSN: 1144-0546 |
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| Вых. Данные | Год: 2023, Том: 47, Номер: 42, Страницы: 19556-19568 Страниц : 1 DOI: 10.1039/d3nj02875e | ||||
| Авторы |
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Реферат:
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, 1
H, 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.
Библиографическая ссылка:
Li J.
, Krasnov V.
, Karpova E.
, Andreev R.
, Genaev A.
, Rumyantseva E.
, Shundrina I.
, Romanov V.
, Selivanova G.
Fluorinated 2,3-diaminophenazines: synthesis, mechanism of formation, and properties
New Journal of Chemistry. 2023. V.47. N42. P.19556-19568. DOI: 10.1039/d3nj02875e WOS Scopus РИНЦ OpenAlex
Fluorinated 2,3-diaminophenazines: synthesis, mechanism of formation, and properties
New Journal of Chemistry. 2023. V.47. N42. P.19556-19568. DOI: 10.1039/d3nj02875e WOS Scopus РИНЦ OpenAlex
Даты:
| Поступила в редакцию: | 21 июн. 2023 г. |
| Принята к публикации: | 28 сент. 2023 г. |
| Опубликована online: | 29 сент. 2023 г. |
| Опубликована в печати: | 14 нояб. 2023 г. |
Идентификаторы БД:
| Web of science: | WOS:001085538500001 |
| Scopus: | 2-s2.0-85174406861 |
| РИНЦ: | 63841666 |
| OpenAlex: | W4387194442 |