Reaction of 3,5-di-(tert-butyl)-o-benzoquinone with arylamines developing to the formation of a pentaheterocyclic 12Н-quinoxaline[2,3-b]phenoxazine system. A deeper insight into the reaction mechanism

Reaction of 3,5-di-(tert-butyl)-o-benzoquinone with arylamines developing to the formation of a pentaheterocyclic 12Н-quinoxaline[2,3-b]phenoxazine system. A deeper insight into the reaction mechanism Full article

Journal

Dyes and Pigments
ISSN: 0143-7208

Output data

Year: 2018, Volume: 150, Pages: 97-104 Pages count : 8 DOI: 10.1016/j.dyepig.2017.11.009

Tags

Phenoxazine, Synthesis, Fluorescence, Molecular structure, Pentacyclic heterocycles

Authors

Ivakhnenko Eugeny P. ¹ , Romanenko Galina V. ² , Kovalenko Anastasia A. ¹ , Revinskii Yurii V. ¹ , Knyazev Pavel A. ¹ , Kuzmin Vladimir A. ³ , Minkin Vladimir I. ¹

Affiliations

1	Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki St., 344090 Rostov on Don, Russian Federation
2	International Tomography Center, Siberian Branch of Russian Academy of Sciences, 3a Institutskaya St., 630090 Novosibirsk, Russian Federation
3	N.M. Emanuel Institute of Biochemical Physics of Russian Academy of Sciences, 4 Kosygina St., 119334 Moscow, Russian Federation

Reaction between sterically crowded 3,5-di-(tert-butyl)-o-benzoquinone and aromatic amines occurring at the oxidative conditions and developing to the formation of compounds 8, derivatives of the pentaheterocyclic 12Н-quinoxaline[2,3-b]phenoxazine system 2 was studied. The products obtained at the intermediate stages, including di-(tert-butyl) derivatives of the tricyclic 10H-phenoxazine system: (E)-N-3Н-phenoxazin-3-ylidene-4-methoxyaniline 3, N-(aryl)-3-arylimine-3Н-phenoxazine-2-amine 4, 1-phenyl-10H-phenoxazine 5 and 1-phenyl- 3H-phenoxazin-3-one 6 were preparatively isolated and their molecular structures determined by X-ray crystallography. A stable 1-phenyl-6,8-di-(tert-butyl)-10H-phenoxazine radical 7, a primary product of oxidation of 5 was prepared and characterized by the ESR spectroscopy. Compounds 8 exhibit strong red luminescence distinguished by small Stokes shifts, short ﬂuorescent lifetimes and high quantum yields.

Ivakhnenko E.P. , Romanenko G.V. , Kovalenko A.A. , Revinskii Y.V. , Knyazev P.A. , Kuzmin V.A. , Minkin V.I.
Reaction of 3,5-di-(tert-butyl)-o-benzoquinone with arylamines developing to the formation of a pentaheterocyclic 12Н-quinoxaline[2,3-b]phenoxazine system. A deeper insight into the reaction mechanism
Dyes and Pigments. 2018. V.150. P.97-104. DOI: 10.1016/j.dyepig.2017.11.009 WOS Scopus

Published print:

Nov 15, 2017

Web of science:	WOS:000427332200014
Scopus:	2-s2.0-85034589049

DB	Citing
Scopus	15
Web of science	13