2,7-Disubstituted 1,3,6,8-tetraazabenzopyrenes: Synthesis, characterization, optical and electrochemical properties

2,7-Disubstituted 1,3,6,8-tetraazabenzopyrenes: Synthesis, characterization, optical and electrochemical properties Full article

Journal

Dyes and Pigments
ISSN: 0143-7208 , E-ISSN: 1873-3743

Output data

Year: 2019, Volume: 168, Pages: 219-227 Pages count : 9 DOI: 10.1016/j.dyepig.2019.04.062

Tags

Tetraazabenzopyrenes; Double peri-annulation; Alkylation; Nucleophilic substitution; Photophysical properties

Authors

Baranov Denis S. ^1,2 , Krivenko Olga L. ¹ , Nevostruev Danil A. ¹ , Glebov Evgeni M. ^1,2 , Uvarov Mikhail N. ^1,2 , Kazantsev Maxim S. ^2,3 , Mostovich Evgeny A. ^2,3 , Kulik Leonid, V ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, VV Voevodsky Inst Chem Kinet & Combust, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk, Russia

The syntheses of 2,7-diamino-1,3,6,8-tetraazabenzopyrene framework was achieved through CuI-catalyzed double annulation of 1,4-diiodoanthraquinone with guanidine. In addition, the preparation of series of 2,7-disubstituted 1,3,6,8-tetraazabenzopyrenes functionalized by NR2, C=O, Cl, alkoxy and phenoxy groups with good yields was achieved through the simple transformations such as diazotization, alkylation and nucleophilic aromatic substitution. The properties of 1,3,6,8-tetraazabenzopyrenes synthesized were studied by DFT-calculations, optical and photoluminescence spectroscopy, cyclic voltammetry and light-induced EPR spectroscopy. The luminescence of amino derivatives is quenched in acidic solutions depending on the degree of protonation.

Baranov D.S. , Krivenko O.L. , Nevostruev D.A. , Glebov E.M. , Uvarov M.N. , Kazantsev M.S. , Mostovich E.A. , Kulik L.V.
2,7-Disubstituted 1,3,6,8-tetraazabenzopyrenes: Synthesis, characterization, optical and electrochemical properties
Dyes and Pigments. 2019. V.168. P.219-227. DOI: 10.1016/j.dyepig.2019.04.062 WOS Scopus РИНЦ

Published print:

Sep 1, 2019

Web of science	WOS:000471733000026
Scopus	2-s2.0-85065059896
Elibrary	38699766
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