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

Andrzej Kaim¹  Ilona Turowska-Tyrk²  KrzysztofA. Konieczny²  Agnieszka Dylong³  Wojciech Przybył³  Karolina Dysz³  KrzysztofA. Bogdanowicz³  Agnieszka Iwan³ 

[1] Faculty of Chemistry, University of Warsaw, 1 Pasteura str., 02-093 Warsaw, Poland;Faculty of Chemistry, Wrocław University of Science and Technology, 27 Wybrzeże Wyspiańskiego, 50-370 Wroclaw, Poland;Military Institute of Engineer Technology, 136 Obornicka str, 50-961 Wroclaw, Poland;

关键词: imines;    azomethines;    crystal structure;    non-covalent interactions;    camforosulphonic acid;    thermographic camera;   

DOI  :  10.3390/ma14081952

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown