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Halogenated Diazabutadiene Dyes: Synthesis, Structures, Supramolecular Features, and Theoretical Studies

Novel halogenated aromatic dichlorodiazadienes were prepared via copper-mediated oxidative coupling between the corresponding hydrazones and CCl(4). These rare azo-dyes were characterized using (1)H and (13)C NMR techniques and X-ray diffraction analysis for five halogenated dichlorodiazadienes. Mul...

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Autores principales: Nenajdenko, Valentine G., Shikhaliyev, Namiq G., Maharramov, Abel M., Bagirova, Khanim N., Suleymanova, Gulnar T., Novikov, Alexander S., Khrustalev, Victor N., Tskhovrebov, Alexander G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7663549/
https://www.ncbi.nlm.nih.gov/pubmed/33138101
http://dx.doi.org/10.3390/molecules25215013
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author Nenajdenko, Valentine G.
Shikhaliyev, Namiq G.
Maharramov, Abel M.
Bagirova, Khanim N.
Suleymanova, Gulnar T.
Novikov, Alexander S.
Khrustalev, Victor N.
Tskhovrebov, Alexander G.
author_facet Nenajdenko, Valentine G.
Shikhaliyev, Namiq G.
Maharramov, Abel M.
Bagirova, Khanim N.
Suleymanova, Gulnar T.
Novikov, Alexander S.
Khrustalev, Victor N.
Tskhovrebov, Alexander G.
author_sort Nenajdenko, Valentine G.
collection PubMed
description Novel halogenated aromatic dichlorodiazadienes were prepared via copper-mediated oxidative coupling between the corresponding hydrazones and CCl(4). These rare azo-dyes were characterized using (1)H and (13)C NMR techniques and X-ray diffraction analysis for five halogenated dichlorodiazadienes. Multiple non-covalent halogen···halogen interactions were detected in the solid state and studied by DFT calculations and topological analysis of the electron density distribution within the framework of Bader’s theory (QTAIM method). Theoretical studies demonstrated that non-covalent halogen···halogen interactions play crucial role in self-assembly of highly polarizable dichlorodiazadienes. Thus, halogen bonding can dictate a packing preference in the solid state for this class of dichloro-substituted heterodienes, which could be a convenient tool for a fine tuning of the properties of this novel class of dyes.
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spelling pubmed-76635492020-11-14 Halogenated Diazabutadiene Dyes: Synthesis, Structures, Supramolecular Features, and Theoretical Studies Nenajdenko, Valentine G. Shikhaliyev, Namiq G. Maharramov, Abel M. Bagirova, Khanim N. Suleymanova, Gulnar T. Novikov, Alexander S. Khrustalev, Victor N. Tskhovrebov, Alexander G. Molecules Article Novel halogenated aromatic dichlorodiazadienes were prepared via copper-mediated oxidative coupling between the corresponding hydrazones and CCl(4). These rare azo-dyes were characterized using (1)H and (13)C NMR techniques and X-ray diffraction analysis for five halogenated dichlorodiazadienes. Multiple non-covalent halogen···halogen interactions were detected in the solid state and studied by DFT calculations and topological analysis of the electron density distribution within the framework of Bader’s theory (QTAIM method). Theoretical studies demonstrated that non-covalent halogen···halogen interactions play crucial role in self-assembly of highly polarizable dichlorodiazadienes. Thus, halogen bonding can dictate a packing preference in the solid state for this class of dichloro-substituted heterodienes, which could be a convenient tool for a fine tuning of the properties of this novel class of dyes. MDPI 2020-10-29 /pmc/articles/PMC7663549/ /pubmed/33138101 http://dx.doi.org/10.3390/molecules25215013 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Nenajdenko, Valentine G.
Shikhaliyev, Namiq G.
Maharramov, Abel M.
Bagirova, Khanim N.
Suleymanova, Gulnar T.
Novikov, Alexander S.
Khrustalev, Victor N.
Tskhovrebov, Alexander G.
Halogenated Diazabutadiene Dyes: Synthesis, Structures, Supramolecular Features, and Theoretical Studies
title Halogenated Diazabutadiene Dyes: Synthesis, Structures, Supramolecular Features, and Theoretical Studies
title_full Halogenated Diazabutadiene Dyes: Synthesis, Structures, Supramolecular Features, and Theoretical Studies
title_fullStr Halogenated Diazabutadiene Dyes: Synthesis, Structures, Supramolecular Features, and Theoretical Studies
title_full_unstemmed Halogenated Diazabutadiene Dyes: Synthesis, Structures, Supramolecular Features, and Theoretical Studies
title_short Halogenated Diazabutadiene Dyes: Synthesis, Structures, Supramolecular Features, and Theoretical Studies
title_sort halogenated diazabutadiene dyes: synthesis, structures, supramolecular features, and theoretical studies
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7663549/
https://www.ncbi.nlm.nih.gov/pubmed/33138101
http://dx.doi.org/10.3390/molecules25215013
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