Cargando…
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...
Autores principales: | , , , , , , , |
---|---|
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 |
_version_ | 1783609652704968704 |
---|---|
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. |
format | Online Article Text |
id | pubmed-7663549 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT nenajdenkovalentineg halogenateddiazabutadienedyessynthesisstructuressupramolecularfeaturesandtheoreticalstudies AT shikhaliyevnamiqg halogenateddiazabutadienedyessynthesisstructuressupramolecularfeaturesandtheoreticalstudies AT maharramovabelm halogenateddiazabutadienedyessynthesisstructuressupramolecularfeaturesandtheoreticalstudies AT bagirovakhanimn halogenateddiazabutadienedyessynthesisstructuressupramolecularfeaturesandtheoreticalstudies AT suleymanovagulnart halogenateddiazabutadienedyessynthesisstructuressupramolecularfeaturesandtheoreticalstudies AT novikovalexanders halogenateddiazabutadienedyessynthesisstructuressupramolecularfeaturesandtheoreticalstudies AT khrustalevvictorn halogenateddiazabutadienedyessynthesisstructuressupramolecularfeaturesandtheoreticalstudies AT tskhovrebovalexanderg halogenateddiazabutadienedyessynthesisstructuressupramolecularfeaturesandtheoreticalstudies |