Diaza-analogs of benzopyrene and perylene containing thienyl and 4-(phenylamino)phenyl groups: Synthesis, characterization, optical and electrochemical properties

Diaza-analogs of benzopyrene and perylene containing thienyl and 4-(phenylamino)phenyl groups: Synthesis, characterization, optical and electrochemical properties Full article

Journal

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

Output data

Year: 2017, Volume: 136, Pages: 707-714 Pages count : 8 DOI: 10.1016/j.dyepig.2016.09.026

Tags

Diazabenzopyrenes; Diazaperylenes; Push-pull polycondensed small molecules; Solid-state luminescence

Authors

Baranov Denis S. ^1,2 , Uvarov Mikhail N. ¹ , Kazantsev Maxim S. ^2,3 , Mostovich Evgeny A. ^2,3 , Glebov Evgeni M. ^1,2 , Gatilov Yurii V. ^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 630090, Russia

Series of 1,8-diazabenzopyrenes and 1,7-diazaperylenes with thienyl or 4-(phenylamino)phenyl groups were designed and synthesized by a one-pot process from the functionalized terminal alkynes and either 1,4- or 1,5-diiodoanthraquinones in order to investigate the effect of extending pi-conjugation at the 2,7 and 2,8-positions on the optical and electrochemical properties. The substances synthesized were characterized by X-ray analysis, cyclic voltammetry, UV-vis and luminescence spectroscopy. Energies and spin-densities of frontier molecular orbitals were calculated by DFT. Practically planar crystal structures of 1,8-diazabenzopyrene and 1,7-diazaperylene with thienyl groups were confirmed by X-ray diffraction data. Solid-state luminescence was obtained for the synthesized substances in drop-casted films and in 1,4-dioxane/water mixtures. (C) 2016 Elsevier Ltd. All rights reserved.

Baranov D.S. , Uvarov M.N. , Kazantsev M.S. , Mostovich E.A. , Glebov E.M. , Gatilov Y.V. , Kulik L.V.
Diaza-analogs of benzopyrene and perylene containing thienyl and 4-(phenylamino)phenyl groups: Synthesis, characterization, optical and electrochemical properties
Dyes and Pigments. 2017. V.136. P.707-714. DOI: 10.1016/j.dyepig.2016.09.026 WOS Scopus РИНЦ

Published print:

Jan 1, 2017

Web of science	WOS:000387837200085
Scopus	2-s2.0-84988481796
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