Synthesis and characterization of new imine liquid crystals based on terminal perfluoroalkyl group

El‐Atawy, Mohamed A.; Omar, Alaa Z.; Alazmi, Mohammed L.; Alsubaie, Mai S.; Hamed, Ezzat A.; Ahmed, Hoda A.

doi:10.1016/j.heliyon.2023.e14871

Cited by 9 publications

(7 citation statements)

References 67 publications

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“…To understand the effect of the terminal benzyloxy substitution on the phase behaviour of the investigated compounds, it is interesting to compare them with related materials reported before with different substitutions having the same aromatic core of compounds I n but without trifluoromethyl substitution (II n ) [40] and thioether moiety (III n ) [41]. The number of carbon atoms in the terminal chain (n) in all compared series also 6, 8 and 12 as those used in compounds I n (Figure 4).…”

Section: Comparison With Related Materialsmentioning

confidence: 99%

“…The selection of a mesogenic core, terminal groups and a flexible chain are the essential specification in the design of new thermotropic LCs [16,[29][30][31][34][35][36][37][38][39]. A para-substituted phenyl ring is used to confirm that the molecules have structural linearity and large molecular polarizability [40]. The mesophase behaviour of compounds of type (E)-3(or4) -(alkyloxy)-N-(trifluoromethyl)benzylideneaniline was previously investigated in our lab using a terminal polar trifluoromethyl substituent [40] as well as another terminal alkoxy side group of varying chain length.…”

Section: Introductionmentioning

confidence: 99%

“…A para-substituted phenyl ring is used to confirm that the molecules have structural linearity and large molecular polarizability [40]. The mesophase behaviour of compounds of type (E)-3(or4) -(alkyloxy)-N-(trifluoromethyl)benzylideneaniline was previously investigated in our lab using a terminal polar trifluoromethyl substituent [40] as well as another terminal alkoxy side group of varying chain length. In that study, [40] found that the polarity and/or polarisability of the mesogenic portion of the molecule, which is indisputably affected by the polarity of the substituent, would consequently affect the polarity of the entire molecular structure by the way the polar substituents interact mesomerically with the rest of the molecule, enhanced the stability of the mesophase.…”

Section: Introductionmentioning

confidence: 99%

“…The mesophase behaviour of compounds of type (E)-3(or4) -(alkyloxy)-N-(trifluoromethyl)benzylideneaniline was previously investigated in our lab using a terminal polar trifluoromethyl substituent [40] as well as another terminal alkoxy side group of varying chain length. In that study, [40] found that the polarity and/or polarisability of the mesogenic portion of the molecule, which is indisputably affected by the polarity of the substituent, would consequently affect the polarity of the entire molecular structure by the way the polar substituents interact mesomerically with the rest of the molecule, enhanced the stability of the mesophase. A later study expanded the [41] investigation to include more compounds of type (E)-4-(alkoxy)-N-(4-(methylthio)benzylidene)aniline [41], where the thioether moiety was connected to the terminal ring.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of New Liquid-Crystalline Compounds Based on Terminal Benzyloxy Group: Characterization, DFT and Mesomorphic Properties

et al. 2023

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The effect of the terminal benzyloxy group on the mesomorphic properties of liquid crystalline materials developed from rod-like Schiff base has been described. For this objective, a novel Schiff base liquid crystal family, specifically new series of Schiff base liquid crystals, namely, (E)-4-(alkyloxy)-N-(4-(benzyloxy)benzylidene)aniline, In, are prepared and investigated in detail. The length of the terminal alkyloxy chain (n) varies amongst the compounds in the series. Where n varies between 6, 8 and 16 carbons. At the other end of the compounds, benzyloxy moiety was attached. The molecular structures of all synthesized compounds were established using different spectroscopic techniques. The molecular self-assembly was explored using differential scanning calorimetry (DSC) and polarized optical microscope (POM). Depending on the length of the terminal alkyloxy chain, only one type of SmA phase with different stability was observed. The previously reported para-substituted systems and the present investigated compounds were compared and discussed. The calculated quantum chemical parameters were computationally correlated using the DFT method via the B3LYP 6-311G(d,p) basis set. The theoretical computations revealed that the length of the alkyl side chain influences the zero-point energy, reactivity and other estimated thermodynamic parameters of benzoyloxy/azomethine derivatives. Furthermore, the FMO energy analysis shows that molecule I16 have higher HOMO energies than the other compounds, and I6 has a much lower LUMO level than the rest.

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Section: Comparison With Related Materialsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of New Liquid-Crystalline Compounds Based on Terminal Benzyloxy Group: Characterization, DFT and Mesomorphic Properties

et al. 2023

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“…Several features of liquid crystal materials are significantly enhanced by the introduction of lateral groups (F, I, Br, CN, NO 2 , CH 3 , or OCH 3 ). The molecular packing disruption that lowers the melting temperature and decreases the stability of liquid crystal phases may be responsible [24][25][26][27][28][29][30][31][32]. Both the features required for technical usage and the alterations to the liquid crystals' attributes may be advantageous for mesomorphism.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Laterally Chloro-Substituted Schiff Base Ester Liquid Crystals: Mesomorphic and Optical Properties

et al. 2023

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A new class of Schiff base/ester compounds: ICln, 4-((2′-chlorophenylimino)methyl)phenyl-4″-alkoxy benzoates, were synthesized and their mesophase characteristics and thermal behavior were evaluated. Differential scanning calorimetry (DSC) was used to study mesophase transitions, and polarized optical microscopy was carried out to identify the phases (POM). The results show that all compounds are monomorphic, and enantiotropic nematic (N) phases were seen at all side chains. It was found that lateral Cl atoms in the terminal benzene ring influence both conformation and mesomorphic properties. Comparisons between the present investigated lateral Cl derivatives and their laterally neat, as well as their isomeric, compounds have been briefly discussed. Results revealed that the insertion of lateral Cl substituent in the molecular structure impacts the type and stability of the formed mesophases. The exchanges of the ester-connecting moiety improve their thermal nematic stability than their previously prepared structurally isomeric derivatives. These compounds exhibit a broad absorption in the UV-Visible region, including a peak in UV region and a tail around 550 nm, and there were observed to be absorption tail increases and energy band gap decreases with the increase of the alkoxy side chain length. The photoluminescence (PL) intensity was noted to be quenched for the bulky alkoxy group ascribed to non-radiative recombination through the defect states. Moreover, time resolved fluorescence decay spectra reveal that both the radiative and non-radiative recombination lifetime increases with the increase of alkoxy side chain length.

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First mesomorphic and DFT characterizations for 3- (or 4-) n-alkanoyloxy benzoic acids and their optical applications

El-Atawy,

Khan,

Popoola

et al. 2023

Heliyon

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Synthesis and characterization of new imine liquid crystals based on terminal perfluoroalkyl group

Cited by 9 publications

References 67 publications

Synthesis of New Liquid-Crystalline Compounds Based on Terminal Benzyloxy Group: Characterization, DFT and Mesomorphic Properties

Synthesis of New Liquid-Crystalline Compounds Based on Terminal Benzyloxy Group: Characterization, DFT and Mesomorphic Properties

Preparation of Laterally Chloro-Substituted Schiff Base Ester Liquid Crystals: Mesomorphic and Optical Properties

First mesomorphic and DFT characterizations for 3- (or 4-) n-alkanoyloxy benzoic acids and their optical applications

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