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 (<i>trans</i>-PPL9) by X-ray diffraction. The imine crystallized in the monoclinic P2<sub>1</sub>/n space group with a = 18.9567(7) Å, b...
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| author | Agnieszka Dylong Karolina Dysz Krzysztof A. Bogdanowicz Wojciech Przybył Krzysztof A. Konieczny Ilona Turowska-Tyrk Andrzej Kaim Agnieszka Iwan |
| author_facet | Agnieszka Dylong Karolina Dysz Krzysztof A. Bogdanowicz Wojciech Przybył Krzysztof A. Konieczny Ilona Turowska-Tyrk Andrzej Kaim Agnieszka Iwan |
| author_sort | Agnieszka Dylong |
| collection | DOAJ |
| 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 (<i>trans</i>-PPL9) by X-ray diffraction. The imine crystallized in the monoclinic P2<sub>1</sub>/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 <sup>1</sup>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. |
| first_indexed | 2024-03-10T12:21:26Z |
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| issn | 1996-1944 |
| language | English |
| last_indexed | 2024-03-10T12:21:26Z |
| publishDate | 2021-04-01 |
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| series | Materials |
| spelling | doaj.art-a70c474323fc4a9789d980253a1ec0b62023-11-21T15:25:14ZengMDPI AGMaterials1996-19442021-04-01148195210.3390/ma14081952Crystal 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 StudiesAgnieszka Dylong0Karolina Dysz1Krzysztof A. Bogdanowicz2Wojciech Przybył3Krzysztof A. Konieczny4Ilona Turowska-Tyrk5Andrzej Kaim6Agnieszka Iwan7Military Institute of Engineer Technology, 136 Obornicka Str., 50-961 Wroclaw, PolandMilitary Institute of Engineer Technology, 136 Obornicka Str., 50-961 Wroclaw, PolandMilitary Institute of Engineer Technology, 136 Obornicka Str., 50-961 Wroclaw, PolandMilitary Institute of Engineer Technology, 136 Obornicka Str., 50-961 Wroclaw, PolandFaculty of Chemistry, Wrocław University of Science and Technology, 27 Wybrzeże Wyspiańskiego, 50-370 Wroclaw, PolandFaculty of Chemistry, Wrocław University of Science and Technology, 27 Wybrzeże Wyspiańskiego, 50-370 Wroclaw, PolandFaculty of Chemistry, University of Warsaw, 1 Pasteura Str., 02-093 Warsaw, PolandMilitary Institute of Engineer Technology, 136 Obornicka Str., 50-961 Wroclaw, PolandThe 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 (<i>trans</i>-PPL9) by X-ray diffraction. The imine crystallized in the monoclinic P2<sub>1</sub>/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 <sup>1</sup>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.https://www.mdpi.com/1996-1944/14/8/1952iminesazomethinescrystal structurenon-covalent interactionscamforosulphonic acidthermographic camera |
| spellingShingle | Agnieszka Dylong Karolina Dysz Krzysztof A. Bogdanowicz Wojciech Przybył Krzysztof A. Konieczny Ilona Turowska-Tyrk Andrzej Kaim Agnieszka Iwan 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 Materials imines azomethines crystal structure non-covalent interactions camforosulphonic acid thermographic camera |
| 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 | imines azomethines crystal structure non-covalent interactions camforosulphonic acid thermographic camera |
| url | https://www.mdpi.com/1996-1944/14/8/1952 |
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