In this work the description, test, and performance of a new vacuum apparatus for thin film vapor deposition (ThinFilmVD) of organic semiconductor materials are presented. The apparatus is able to fabricate single, multilayer/composites, or hybrid thin films using four independent, organic or inorganic, vapor deposition sources (Knudsen cells type), and the vapor mass flow is condensed onto a substrate surface (temperature regulated). The same apparatus could be also used to measure vapor pressures according to the Knudsen effusion methodology. Vapor pressures and thermodynamic properties of sublimation measured by Knudsen effusion of some reference organic materials (benzoic acid, anthracene, triphenylene, benzanthrone, 1,3,5-triphenylbenzene, perylene) were used to evaluate and test the performance of the apparatus. Moreover, nanostructures of thin films and composite materials of relevant charge transport and electroluminescent materials were deposited onto an indium−tin oxide (ITO) surface, and the morphology and thin film thickness were evaluated by scanning electron microscopy (SEM), exploring the effect of different mass flow rates and deposition time. The new physical vapor deposition apparatus based in four Knudsen effusion cells with an accurate mass flow control was designed to assemble well-defined (composition, morphology, thickness) thin films of organic semiconductors based on their volatility. The described apparatus presents a high versatility to the fabrication of single/multilayer thin films, as-grown crystals, and hybrid micro-and nanostructured materials.
A comprehensive study of the solution and solvation of linear alcohols (propan-1-ol, butan-1-ol and pentan-1-ol) in ionic liquids (ILs) is presented. The effect of the alkyl chain size of both alcohols and ILs (1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [CnC1im][NTf2], ionic liquid series) on the thermodynamic properties of solution and solvation was used to obtain insight into the interactions between alcohols and ILs. Alcohols were used as molecular probes to ascertain whether their solvation in ILs would reflect IL nanostructuration. A trend shift was found in the values of enthalpy of solution and solvation for the [CnC1im][NTf2] series at a critical alkyl size (CAS) of C6. Further, the effect of the hydrogen bond basicity of the anion in the solvation of alcohols was explored based on the comparative study of the solvation of propan-1-ol in two different IL series, 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [CnC1im][NTf2] and hexafluorophosphate [CnC1im][PF6]. The results obtained provide experimental support for the strength of hydrogen bonds between the alcohols and the NTf2 and PF6 anions, providing insights into the IL intermolecular interactions, namely by indicating the ability of the alcohols to discriminate the IL anion hydrogen bond basicity.
This work presents a comprehensive evaluation of the phase behaviour and cohesive enthalpy of protic ionic liquids (PILs) composed of 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) organic superbases with short-chain length (acetic, propionic and butyric) carboxylic acids. Glass transition temperatures, T, and enthalpies of vaporization, ΔH, were measured for six [BH][A] (1 : 1) PILs (B = DBN, DBU; A = MeCOO, EtCOO, nPrCOO), revealing more significant changes upon increasing the number of -CH- groups in the base than in the acid. The magnitude of ΔH evidences that liquid PILs have a high proportion of ions, although the results also indicate that in DBN PILs the concentration of neutral species is not negligible. In the gas phase, these PILs exist as a distribution of ion pairs and isolated neutral species, with speciation being dependent on the temperature and pressure conditions - at high temperatures and low pressures the separated neutral species dominate. The higher T and ΔH of the DBU PILs are explained by the stronger basicity of DBU (as supported by NMR and computational calculations), which increases the extent of proton exchange and the ionic character of the corresponding PILs, resulting in stronger intermolecular interactions in condensed phases.
We have explored the branching of ionic liquid cation sidechains utilizing silicon as the backbone and found this structural feature to lead to fluids of remarkably low density and viscosity....
In this work, we studied the effect of anion and cation properties on the interaction of alcohols with ionic liquids (ILs), using propan-1-ol as a molecular probe. The enthalpies of solution at infinite dilution of propan-1-ol in several ILs were measured by isothermal titration calorimetry (ITC). The calorimetric results were analysed together with molecular dynamics simulation and quantum chemical calculations of the interaction of the hydroxyl group of propan-1-ol with the anions. The results evidenced the role of the anion's basicity in the intermolecular interactions of alcohols and ionic liquids and further revealed a secondary effect of the cation nature on the solvation process. The effect of the anion basicity on the strength of the interaction of alcohols with ionic liquids was evaluated by comparing the results obtained for ILs with the same cation and different anions, [CCim][anion] (anions NTf, PF, FAP, DCA and TFA). The effect of the cation (size, aromaticity, charge distribution, and acidity) was explored using five different cations of the NTf series, [cation][NTf] (cations CCim, CCpirr, Cpy, CCpip, and CCCim).
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