A new class of discotics derived from tris(N-salicylideneaniline)s have been synthesized and their thermal and photophysical properties are investigated. These systems with outer 1,3,4-oxadiazole wings exist in an inseparable mixture of two keto-enamine tautomeric forms with C(3h) and C(s) rotational symmetries, and self-assemble into fluid columnar phase over a wide thermal range as evidenced by several complementary studies. They possess emissive characteristics in both solution and columnar states; the blue light (lambda = 474 nm) emission has been evidenced for the former state.
Columnar phases formed by the stacking of disclike molecules with an intimate π-π overlap forms a 1D pathway for the anisotropic charge migration along the columns. Columnar phases have great potential in organic electronic devices to be utilized as active semiconducting layers in comparison to organic single crystals or amorphous polymers in terms of processability, ease of handling, and high charge carrier mobility. Intelligent molecular engineering of perylene and its derivatives provided access to tune the physical properties and self-assembly behavior. The columnar phase formed by perylene derivatives has great potential in the fabrication of organic electronic devices. There are several positions on the perylene molecule, which can be functionalized to tune its self-assembly, as well as optoelectronic properties. Thus, many liquid-crystalline molecules stabilizing the columnar phase, which are based on perylene tetraesters, perylene diester imides, and perylene bisimides, have been synthesized over the years. Their longitudinal and laterally extended derivatives, bay-substituted derivatives exhibiting a columnar phase, are reported. In addition, several liquid-crystalline oligomers and polymers based on perylene derivatives were also reported. All such modifications provide an option to tune the energy levels of frontier molecular orbitals with respect to the work function of the electrodes in devices and also the processability of such materials. In this feature article, we attempt to provide an overview of the molecular design developed to tune the applicable properties and self-assembly of perylene derivatives as well as recent developments related to their application in the fabrication of organic solar cells, organic light-emitting diodes, and organic field-effect transistors.
Two series of a unique class of columnar liquid crystals derived from tris(N-salicylideneaniline)s [TSANs] in which the proton and the electron interact with each other through the H-bonding environment are reported. The synthesis is carried out by condensing 1,3,5-triformylphloroglucinol with the respective dialkoxyanilines or trialkoxyanilines. 1H NMR and 1H-1H COSY NMR studies revealed their existence as an inseparable mixture of two keto-enamine tautomeric forms with C3h and Cs rotational symmetries instead of the expected enol-imine form. The influence of the number of peripheral alkoxy tails on the columnar mesomorphic behavior is investigated by using polarizing optical microscopy, differential scanning calorimetry, and X-ray scattering. The fluid/glassy columnar states probed for a number of representative compounds confirmed the D6h (hexagonal) or D2h (rectangular) symmetry of the columns. The electronic absorption and emission characteristics of these compounds have been studied in both mesomorphic and solution states. Of special interest, the photoluminescence spectra of solution and fluid/glassy two-dimensional structure evidently disclose the promising light generating capability of these new discotics systems.
Ionic liquid crystals have emerged as a new class of functional soft materials in the last two decades, and they exhibit synergistic characteristics of ionic liquids and liquid crystals such as macroscopic orientability, miscibility with various species, phase stability, nanostructural tunability, and polar nanochannel formation. Owing to these characteristics, the structures, properties, and functions of ionic liquid crystals have been a hot topic in materials chemistry, finding various applications including host frameworks for guest binding, separation membranes, ion-/proton-conducting membranes, reaction media, and optoelectronic materials. Although several excellent review articles of ionic liquid crystals have been published recently, they mainly focused on the fundamental aspects, structures, and specific properties of ionic liquid crystals, while these applications of ionic liquid crystals have not yet been discussed at one time. The aim of this feature article is to provide an overview of the applications of ionic liquid crystals in a comprehensive manner.
Room temperature columnar liquid crystals and their application in OLEDs.
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