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

Описание

Тип публикации: статья из журнала

Год издания: 2018

Идентификатор DOI: 10.1016/j.dyepig.2017.11.009

Ключевые слова: Fluorescence, Molecular structure, Pentacyclic heterocycles, Phenoxazine, Synthesis

Аннотация: 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-Показать полностью(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. © 2017 Elsevier Ltd

Ссылки на полный текст

Издание

Журнал: Dyes and Pigments

Выпуск журнала: Vol. 150

Номера страниц: 97-104

Издатель: Elsevier Ltd

Авторы

  • Ivakhnenko E.P. (Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki St., Rostov on Don, Russian Federation)
  • Romanenko G.V. (International Tomography Center, Siberian Branch of Russian Academy of Sciences, 3a Institutskaya St., Novosibirsk, Russian Federation)
  • Kovalenko A.A. (Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki St., Rostov on Don, Russian Federation)
  • Revinskii Y.V. (Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki St., Rostov on Don, Russian Federation)
  • Knyazev P.A. (Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki St., Rostov on Don, Russian Federation)
  • Kuzmin V.A. (N.M. Emanuel Institute of Biochemical Physics of Russian Academy of Sciences, 4 Kosygina St., Moscow, Russian Federation)
  • Minkin V.I. (Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki St., Rostov on Don, Russian Federation)

Вхождение в базы данных