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

Autor: Agnieszka Dylong, Karolina Dysz, Krzysztof A. Bogdanowicz, Wojciech Przybył, Krzysztof A. Konieczny, Ilona Turowska-Tyrk, Andrzej Kaim, Agnieszka Iwan
Jazyk: angličtina
Rok vydání: 2021
Předmět:
Zdroj: Materials, Vol 14, Iss 8, p 1952 (2021)
Druh dokumentu: article
ISSN: 1996-1944
DOI: 10.3390/ma14081952
Popis: 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 P21/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 1H 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.
Databáze: Directory of Open Access Journals
Externí odkaz:
Nepřihlášeným uživatelům se plný text nezobrazuje