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Two bent-shaped imines (9E)-N-(3-((E)-(4-hexadecylphenylimino)methyl)benzylidene)-4-hexadecylbenzenamine (SL1) and (10E)-N-(3-((E)-(4-(perfluorooctyl)phenylimino)methyl)benzylidene)-4-(perfluorooctyl)benzenamine (SL2) were prepared by condensation reaction in N,N-dimethylacetamide to study their thermal, structural and electrochemical properties, as well as their mixtures with titanium dioxide. Chemical structure, temperature and TiO2 influences on the phase transition temperatures, enthalpy, texture and molecular dynamics of both imines were investigated by differential scanning calorimetry, polarising optical microscopy and Fourier transform middle-infrared absorption spectroscopy during heating and cooling. Changes in the surface morphology of the imines and their mixtures with TiO2 were registered by atomic force microscopy. X-ray study showed the tendency to form lamellas in the case of SL2 as an effect of the presence of two terminal perfluorinated alkyl chains connected to a polar mobile aromatic core, which resulted in microsegregation. Additionally, TiO2 influences the energy gap and HOMO-LUMO levels of imines as was detected by cyclic voltammetry. Finally, devices with two types of architectures, such as ITO/TiO2/SL1(or P3HT)/Au and ITO/TiO2/SL1:P3HT/Au were constructed and investigated under irradiation intensity of 97.7 mW/cm2. [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

Planar perovskite solar cells were fabricated on F-doped SnO2 (FTO) coated glass substrates, with 4,4'-((1E,1'E)-((1,2,4-thiadiazole-3,5-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(N,N-di-p-tolylaniline) (bTAThDaz) as hole transport material. This imine was synthesized in one step reaction, starting from commercially available and relatively inexpensive reagents. Electrochemical, optical, electrical, thermal and structural studies including thermal images and current-voltage measurements of the full solar cell devices characterize the imine in details. HOMO-LUMO of bTAThDaz were investigated by cyclic voltammetry (CV) and energy-resolved electrochemical impedance spectroscopy (ER-EIS) and were found at −5.19 eV and −2.52 eV (CV) and at −5.5 eV and −2.3 eV (ER-EIS). The imine exhibited 5% weight loss at 156 °C. The electrical behavior and photovoltaic performance of the perovskite solar cell was examined for FTO/TiO2/perovskite/bTAThDaz/Ag device architecture. Constructed devices exhibited good time and air stability together with quite small effect of hysteresis. The observed solar conversion efficiency was 14.4%. [ABSTRACT FROM AUTHOR]

In this study new symmetrical and unsymmetrical imines based on 4-[4-(4-fluorophenyl)1,3-thiazol-2-yl]aniline and 2,2′,5′,2"-terthiophene-5,5"-dicarboxaldehyde or 2,2':5′, 2"-terthiophene-5-carboxaldehyde, respectively, were synthesized by melt condensation with the yield of 86% and 40%. The 5% weight loss of the imines was found in temperature range from 294 to 390 °C in nitrogen, depending on the symmetry of aldehyde used in synthesis. The band gap of symmetrical imine (PV-BLJ-SC13) is lower by about ∼0.33 eV than that of unsymmetrical PV-BLJ-SC14. For both imines the electron density of HOMO level is mainly located on thiophene moieties and is extended to imine bonds in thiazole rings and imine moieties. The theoretical calculations of their HOMO-LUMO levels by DFT methods were also provided. The UV–Vis absorption spectra and cyclic voltammograms of imines both in the form of thin films cast on the electrode as well as dissolved in 1,2-dichloromethane were studied to determine the electrochemical and optical band gap energies as well as correlate the positions of HOMO and LUMO levels obtained by DFT and electrochemical methods. The resistance of imines was approximately 113.8 Ω and 102.4 Ω for PV-BLJ-SC13 and PV-BLJ-SC14, respectively as determined by IR thermal images and have a tendency to decrease by about 17–24 Ω when mixed with PTB7 and PC 71 BM. Both imines showed very bright luminescence. Moreover, optical absorption, photoluminescence and IR thermal images were measured for imine:PTB7 or imine:PTB7:PC 71 BM composite. Finally, simple organic solar cells based on (PTB7:imine):PC 71 BM in weight ratio (4:1):8 and (8:1):13 w/w were constructed and characterized. The highest power conversion efficiency, which was equal to 0.42% was determined for the ITO/PEDOT:PSS/PTB7:PV-BLJ-SC13:PC 71 BM (4:1):8/Al device. In addition, the power conversion efficiency was strongly dependent on the weight ratio of imine in active layer. [ABSTRACT FROM AUTHOR]

Organic–inorganic hybrids based on liquid crystalline symmetrical imine (8Z)-N-(4-((Z)-(4-pentylphenylimino)methyl)benzylidene)-4-pentylbenzenamine (AZJ1) with two aliphatic chains and TiO2 nanomaterials were obtained and investigated taking into account thr crystallographic form of titanium dioxide i.e., anatase versus rutile. The type of TiO2 influences the mesomorphic properties of imine AZJ1, as observed by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM) techniques. Fourier-Transform Infrared Spectroscopy (FT-IR) was used to investigate the interactions of oxygen vacancies located on the TiO2 surface with the studied AZJ1 imine together with studying the influence of temperature. Both imine:TiO2 anatase versus rutile hybrids possessed the highest occupied molecular orbital (HOMO) levels of about −5.39 eV (AZJ1:anatase) and −5.33 eV (AZJ1:rutile) and the lowest unoccupied molecular orbital (LUMO) levels of about −2.24 eV. The presence of TiO2 in each hybrid did not strongly affect the redox properties of imine AZJ1. Organic devices with the configuration of ITO/TiO2/AZJ1 (or AZJ1:TiO2 anatase versus rutile)/Au were fabricated and investigated in the presence and absence of visible light irradiation with a light intensity of 93 mW/cm2. Finally, to analyze defects in the constructed organic devices we used thermal imaging and atomic force microscopy (AFM). The addition of TiO2 in both crystallographic forms has a positive influence on layer-forming properties that manifests itself as a very homogenous heat distribution for the whole sample. [ABSTRACT FROM AUTHOR]