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• 190371-57-4 (E)-1-(3,4-bis(hexyloxy)phenyl)-2-(3,5-dimethoxyphenyl)ethene 
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• 138433-03-1 (E)-3,4-bis(hexyloxy)-N-phenylbenzaldimin 

Relevant academic research and scientific papers

Synthesis and mesomorphic characterization of some novel steroidal mesogens: A structure–property correlation

The steroidal derivatives are found to be extremely good mesogens since their inception. Because of their inherent chirality, they have the potential to induce a wide variety of liquid crystalline phases, including frustrated phases depending upon the structure of the steroidal skeleton and the substituents attached. In this report, a series of novel monoalkoxy and dialkoxy benzoate derivatives of ergosterol and a few monoalkoxy derivatives of stigmasterol have been synthesized and their mesomorphic property has been investigated. The derivatives exhibited various mesophases including SmA, SmC*, N*, TGB and blue phases. Also, the gelation ability of some of these derivatives with various organic solvents has been examined. Furthermore, the mesomorphism of these derivatives has been compared with the analogous cholesteryl counterparts.

Effect of regioisomerism on the self-assembly, photophysical and gelation behavior of aroylhydrazone based polycatenars: Synthesis and characterization

In this paper we report five series of aroylhydrazone based polycatenars differing from each other in number and position of alkoxy chains on one end of the core; keeping other end the same. A systematic variation in the structures was carried out to understand the effect of position and chain length on the mesophase behavior. In the case of single alkoxy chain at 4-position, there is a transition from Smectic C to Smectic A mesophase during cooling and Smectic A to Smectic C transition in heating cycle in all the homologues except n = 6 & n = 8. In the case of two alkoxy chains at 3-, 5-positions, the compounds are non-mesogenic in nature. On changing the position of alkoxy chains from 3-, 5-positions to 3-, 4-positions, intermolecular forces weaken and these compounds become liquid crystalline and show columnar rectangular mesophase resulting from the effect of regioisomerism. Moving on to the series with three alkoxy chains, it was observed that 2-, 3-, 4-trialkoxy substituted compounds exhibit columnar rectangular mesophase except lower chain length (n = 6 & 8) while 3-, 4-, 5-trialkoxy substituted aroylhydrazones show columnar rectangular mesophase; except n = 10 which shows columnar oblique mesophase. Thus it was established that on increasing density of alkoxy chains around one terminal, mesophase changes from smectic to columnar mesophase. Temperature dependent Raman studies confirm the presence of intermolecular hydrogen bonding. Further, effect of substitution pattern did not show much influence on the photophysical properties of the mesogenic series in solid and solution state. However, the non-mesogenic series showed a different absorption and emission transition from the mesogenic series in solid and solution state. Solid state fluorescence studies show almost similar emission maxima in all the series. However, it was also noticed that non-mesogenic series show maximum red shifted emission maxima in solid state as compared to that of solution. All the series showed good gelation properties with less than 1% CGC (wt%) suggesting the strong ability of molecules to form gel. These H-bonded liquid-crystalline gels have immense potential for applications in emissive displays.

Peripheral Substitution of Tetraphenyl Porphyrins: Fine-Tuning Self-Assembly for Enhanced Electroluminescence

This study reports the synthesis of two novel zinc porphyrin families bearing four or eight alkoxy chains at their peripheral phenyl rings, with the length of the alkoxy chains ranging from 2, to 6, and to 12 carbon atoms. All zinc porphyrin derivatives were fully characterized with respect to their photophysical and electrochemical features. The zinc porphyrins could be processed into thin films which, depending on the length of the alkoxy chains on the aryl substituents, were found to be either of an ordered or a disordered nature, as it is revealed by spectroscopic and microscopic techniques. The films containing ordered self-assemblies displayed significantly enhanced electrical conductivity compared to the disordered films. This led to remarkable differences regarding their electroluminescence response that occurs at lower bias. Furthermore, their luminous efficiency was of almost one order of magnitude higher than that of disordered films.

Optoelectronic exploration of novel non-symmetrical star-shaped discotic liquid crystals based on cyanopyridine

A novel family of non-symmetrical star-shaped cyanopyridine based discotic liquid crystals (CPBz6, CPBz8 and CPBz12) was designed and synthesized, as potential luminescent materials for optoelectronic applications. The length of one of the arms in the design was systematically varied to determine the structure-property relationships. Evidently, all of the compounds exhibited a highly prospective ordered columnar mesomorphism stabilized at ambient temperature with advantageous very low isotropization temperatures. Furthermore, their photophysical characteristics were investigated in depth, both in solution and in the liquid crystal (LC) state. The discotics were found to be intense blue emitters with reasonably good quantum efficiency. Their dynamic intramolecular charge-transfer (ICT) behaviour was confirmed by steady-state absorption and fluorescence spectral analysis in varied solvent polarity. Furthermore, their electrochemical properties were studied from the combination of an experimental method and the theoretical simulations, which elucidated the low laying frontier molecular orbitals (FMOs) with a narrow energy band gap of ～2.0 eV. The resulted visually perceivable emission with favourable energy levels showcases their possible application in electronic display devices.

Hydrogen bond-driven columnar self-assembly of electroluminescent D-A-D configured cyanopyridones

Herein, we report the design and synthesis of a new series of flying bird-shaped liquid crystalline (LC) cyanopyridone derivatives with a D-A-D architecture, CPO-1 to CPO-4. Their mesomorphic, photophysical, electrochemical, and electroluminescence charac

Molecular order and mesophase investigation of thiophene-based forked mesogens

Thiophene-based rodlike molecules constructed from a three phenyl ring core and terminal dialkoxy chains recognized as forked mesogens are synthesized, and their mesophase properties as well as the molecular order are investigated. The synthesized forked

Tuning the thermotropic properties of liquid crystalline p-substituted aroylhydrazones

The synthesis and mesomorphic properties of forty substituted aroylhydrazones with peripheral mono-, di- and tri- alkoxy chains derived from a p-amino aroylhydrazone core are described. The compounds with two side chains exhibited a smectic A phase, while the compounds with six soft alkoxy side chains at symmetrical positions formed a rectangular columnar mesophase. The structures of these mesophases were confirmed by differential scanning calorimetry (DSC) analysis, polarized optical microscopy (POM) and powder X-ray diffraction (XRD) studies. Raman studies with the help of density functional theory on some of the mesogenic members have been performed to understand the changes in the intermolecular interactions during phase transitions. A structure-property relationship has been deduced, and mesogenic properties are found to be dependent on the chain length, density and position of the alkoxy chains around the molecular core.

Facile bottom-up synthesis of coronene-based 3-fold symmetrical and highly substituted nanographenes from simple aromatics

A facile and efficient self-sorting assemble (CSA) strategy has been paved for bottom-up construction of the 3-fold symmetrical and highly substituted hexa-cata-hexabenzocoronenes (c-HBCs), the trithieno analogues, and larger disc-shaped PAHs from simple

Supergelation via purely aromatic π-π Driven self-assembly of pseudodiscotic oxadiazole mesogens

A series of highly luminescent oxadiazole-based stilbene molecules (OXD4, OXD8, OXD10, and OXD12) exhibiting interesting enantiotropic liquid crystalline and gelation properties have been synthesized and characterized. The molecules possessing longer alkyl substituents, OXD10 and OXD12, possess a pseudodisc shape and are capable of behaving as supergelators in nonpolar solvents, forming self-standing gels with very high thermal and mechanical stability. Notably the self-assembly of these molecules, which do not possess any hydrogen-bonding motifs normally observed in most reported supergelators, is driven purely by π-stacking interactions of the constituent molecules. The d-spacing ratios estimated from XRD analysis of OXD derivatives possessing longer alkyl chains show that the molecules are arranged in a columnar fashion in the mesogens and the self-assembled nanofibers formed in the gelation process.

Self-assembly of hekates-tris(N -salicylideneaniline)s into columnar structures: Synthesis and characterization

Two series of new, photoluminescent star-shaped discotic liquid crystals, recently termed as "hekates", derived from tris(N-salicylideneaniline) s (TSANs), were synthesized by the facile threefold condensation of 3,4-bis(alkoxy)phenyl 4-aminobenzoates/3,4,5-tris(alkoxy) phenyl 4-aminobenzoates with 1,3,5-triformylphloroglucinol and characterized. These two series of discotics with six and nine peripheral n-alkoxy tails were especially designed and accomplished to understand the relation between mesomorphic/photophysical properties and molecular structure. Proton NMR spectral analysis revealed their existence as an inseparable mixture of two keto-enamine tautomeric forms featuring C3h and Cs rotational symmetries. A systematic study into the thermotropic liquid crystal behavior using polarizing optical microscopy, differential scanning calorimetry, and X-ray scattering confirmed the presence of columnar (Col) phase in vast majority of the TSANs prepared. The two-dimensional (2D) lattices of these fluid columnar phases were found to be characteristic of hexagonal Col (Col h), rectangular Col (Colr), or oblique Col (Col ob) phases depending on the number/length of the peripheral flexible chains. The stabilization of the Colob phase, a less commonly found fluid columnar structure, and the first of its kind in TSAN systems, implies very intensive intermolecular (face-to-face) interactions among the TSAN cores within the column. The photophysical properties were investigated both in solution and the columnar states by UV-vis absorption and photoluminescence; markedly, the solution state emits light in the blue region. The light-emitting ability of the Col phase is particularly significant given the possibility that, in such cores, the protons and electrons interact with each other through the H-bonding environment.