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Crystal Structure Determination of 4-[(Di-p-tolyl-amino)-benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine along with Selected Properties of Imine in Neutral and Protonated Form with Camforosulphonic Acid: Theoretical and Experimental Studies
The crystal structure was determined for the first time for 4-[(di-p-tolyl-amino)benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine (trans-PPL9) by X-ray diffraction. The imine crystallized in the monoclinic P2(1)/n space group with a = 18.9567(7) Å, b = 6.18597(17) Å, c = 22.5897(7) Å, and...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8070542/ https://www.ncbi.nlm.nih.gov/pubmed/33924588 http://dx.doi.org/10.3390/ma14081952 |
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author | Dylong, Agnieszka Dysz, Karolina Bogdanowicz, Krzysztof A. Przybył, Wojciech Konieczny, Krzysztof A. Turowska-Tyrk, Ilona Kaim, Andrzej Iwan, Agnieszka |
author_facet | Dylong, Agnieszka Dysz, Karolina Bogdanowicz, Krzysztof A. Przybył, Wojciech Konieczny, Krzysztof A. Turowska-Tyrk, Ilona Kaim, Andrzej Iwan, Agnieszka |
author_sort | Dylong, Agnieszka |
collection | PubMed |
description | The crystal structure was determined for the first time for 4-[(di-p-tolyl-amino)benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine (trans-PPL9) by X-ray diffraction. The imine crystallized in the monoclinic P2(1)/n space group with a = 18.9567(7) Å, b = 6.18597(17) Å, c = 22.5897(7) Å, and β = 114.009(4)°. Intermolecular interactions in the PPL9 crystal were only weak C−H⋯N hydrogen bonds investigated using the Hirshfeld surface. The electronic and geometric structure of the imine were investigated by the density functional theory and the time-dependent density-functional theory. The properties of the imine in neutral and protonated form with camforosulphonic acid (CSA) were investigated using cyclic voltammetry, UV–vis and (1)H NMR spectroscopy. Theoretical and experimental studies showed that for the 1:1 molar ratio the protonation occured on nitrogen in pyridine in the PPL9 structure, as an effect of Brönsted acid–base interactions. Thermographic camera was used to defined defects in constructed simple devices with ITO/PPL9 (or PPL9:CSA)/Ag/ITO architecture. In conclusion, a thermally stable imine was synthesized in crystalline form and by CSA doping, a modification of absorption spectra together with reduction of overheating process was observed, suggesting its potential application in optoelectronics. |
format | Online Article Text |
id | pubmed-8070542 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-80705422021-04-26 Crystal Structure Determination of 4-[(Di-p-tolyl-amino)-benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine along with Selected Properties of Imine in Neutral and Protonated Form with Camforosulphonic Acid: Theoretical and Experimental Studies Dylong, Agnieszka Dysz, Karolina Bogdanowicz, Krzysztof A. Przybył, Wojciech Konieczny, Krzysztof A. Turowska-Tyrk, Ilona Kaim, Andrzej Iwan, Agnieszka Materials (Basel) Article The crystal structure was determined for the first time for 4-[(di-p-tolyl-amino)benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine (trans-PPL9) by X-ray diffraction. The imine crystallized in the monoclinic P2(1)/n space group with a = 18.9567(7) Å, b = 6.18597(17) Å, c = 22.5897(7) Å, and β = 114.009(4)°. Intermolecular interactions in the PPL9 crystal were only weak C−H⋯N hydrogen bonds investigated using the Hirshfeld surface. The electronic and geometric structure of the imine were investigated by the density functional theory and the time-dependent density-functional theory. The properties of the imine in neutral and protonated form with camforosulphonic acid (CSA) were investigated using cyclic voltammetry, UV–vis and (1)H NMR spectroscopy. Theoretical and experimental studies showed that for the 1:1 molar ratio the protonation occured on nitrogen in pyridine in the PPL9 structure, as an effect of Brönsted acid–base interactions. Thermographic camera was used to defined defects in constructed simple devices with ITO/PPL9 (or PPL9:CSA)/Ag/ITO architecture. In conclusion, a thermally stable imine was synthesized in crystalline form and by CSA doping, a modification of absorption spectra together with reduction of overheating process was observed, suggesting its potential application in optoelectronics. MDPI 2021-04-13 /pmc/articles/PMC8070542/ /pubmed/33924588 http://dx.doi.org/10.3390/ma14081952 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Dylong, Agnieszka Dysz, Karolina Bogdanowicz, Krzysztof A. Przybył, Wojciech Konieczny, Krzysztof A. Turowska-Tyrk, Ilona Kaim, Andrzej Iwan, Agnieszka Crystal Structure Determination of 4-[(Di-p-tolyl-amino)-benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine along with Selected Properties of Imine in Neutral and Protonated Form with Camforosulphonic Acid: Theoretical and Experimental Studies |
title | Crystal Structure Determination of 4-[(Di-p-tolyl-amino)-benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine along with Selected Properties of Imine in Neutral and Protonated Form with Camforosulphonic Acid: Theoretical and Experimental Studies |
title_full | Crystal Structure Determination of 4-[(Di-p-tolyl-amino)-benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine along with Selected Properties of Imine in Neutral and Protonated Form with Camforosulphonic Acid: Theoretical and Experimental Studies |
title_fullStr | Crystal Structure Determination of 4-[(Di-p-tolyl-amino)-benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine along with Selected Properties of Imine in Neutral and Protonated Form with Camforosulphonic Acid: Theoretical and Experimental Studies |
title_full_unstemmed | Crystal Structure Determination of 4-[(Di-p-tolyl-amino)-benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine along with Selected Properties of Imine in Neutral and Protonated Form with Camforosulphonic Acid: Theoretical and Experimental Studies |
title_short | Crystal Structure Determination of 4-[(Di-p-tolyl-amino)-benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine along with Selected Properties of Imine in Neutral and Protonated Form with Camforosulphonic Acid: Theoretical and Experimental Studies |
title_sort | crystal structure determination of 4-[(di-p-tolyl-amino)-benzylidene]-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-imine along with selected properties of imine in neutral and protonated form with camforosulphonic acid: theoretical and experimental studies |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8070542/ https://www.ncbi.nlm.nih.gov/pubmed/33924588 http://dx.doi.org/10.3390/ma14081952 |
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