Discotic mesogens based on triphenylene-fused benzimidazole or perimidine: facile synthesis, mesomorphism, optical properties and self-assembly

Fan, S. M.; Xu, Hong-Tian; Li, Qiang-Gen; Fang, Dong‐Mei; Yu, Wenhao; Hu, Ping; Zhao, Ke‐Qing; Feng, Chun; Wang, Bi‐Qin

doi:10.1080/02678292.2019.1704898

Cited by 19 publications

(3 citation statements)

References 63 publications

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“…Imidazole salts are one of the potential liquid crystal compounds. Imidazoles can be quaternized to generate ionic liquids and LCs [ 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Novel Imidazole Liquid Crystals; Experimental and Computational Approaches

et al. 2022

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The liquid crystalline materials named (E)-4-(2-(4-oxo-5,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)hydrazineylidene)methyl)phenyl and 4-(alkoxy)benzoate, In, were synthesized and their mesomorphic behaviors were examined. The chemical structures of the produced compounds were confirmed by Fourier-transform infrared spectroscopy (FT-IR), NMR, and elemental analysis. Differential scanning calorimetry (DSC) and polarized optical microscopy were used to investigate the mesomorphic properties of designed heterocyclic derivatives. All the compounds tested had suitable thermal stability and enantiotropic behavior of smectogenic temperature ranges. Furthermore, the enantiotropic smectic C phases were observed to cover all the homologues. Moreover, computational investigations corroborated the experimental findings of the mesomorphic behavior. The reactivity parameters were computed for the derivatives and linked with the experimental data. Theoretical calculations revealed that the polarizability of the studied series increases with the chain length, whereas the HOMO–LUMO energy gap or other reactivity descriptors were less sensitive to the size of the system. On the other hand, the predicted thermodynamic parameters revealed the size dependence of thermal stability of the compounds.

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“…Imidazole salts are one of the potential liquid crystal compounds. Imidazoles can be quaternized to generate ionic liquids and LCs [ 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Novel Imidazole Liquid Crystals; Experimental and Computational Approaches

et al. 2022

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“…Over the past few years, thiadiazoles [19,20], oxadiazoles [21][22][23], benzoquinoxalines [24,25], benzimidazoles [26,27], benzoxazoles [28,29], and diimides [30][31][32] have recently been explored as acceptor entities to obtain diverse types of architectural units and liquid crystalline properties. Among heterocycles, Isoindoline-1,3-dione (phthalimide), a significant class of compounds, has attracted significant attention and remained a centre of interest among researchers in the fields such as organic chemistry, medicinal applications, analytical and coordination chemistry.…”

Section: Introductionmentioning

confidence: 99%

Solvent-Free Mechanochemical Synthesis of High Transition Biphenyltetracarboxydiimide Liquid Crystals

et al. 2021

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A series of high temperature alkyl and alkoxy biphenyltetracarboxydiimide liquid crystals have been prepared under ball mill method using solvent-free mechanochemical approach. The thermal properties of the prepared compounds were investigated by deferential scanning calorimetry (DSC) measurements and the textures were identified by polarized optical microscope (POM). The compounds showed smectic mesomorphic behaviour. The results showed the increasing nature of transition temperature Cr-SmC with chain length with increments of the SmC mesophase range. However, the mesophase range of the SmA was decreased with the terminal chain length either for the alkyl or alkoxy terminal groups. Moreover, the DFT theoretical calculations have been conducted give a detailed projection of the structure of the prepared compounds. A conformational investigation of the biphenyl part has been studied. A deep illustration of the experimental mesomorphic behaviour has been discussed in terms of the calculated aspect ratio. A projection of the frontier molecular orbitals as well as molecular electrostatic potential has been studied to show the effect of the polarity of the terminal chains on the level and the gab of the FMOs and the distribution of electrostatic charges on the prepared molecules.

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“…Furthermore, its derivatives behave as fluorescent chemo-sensors and stoppers for supramolecules, generate photochemic memory devices, intermediate in organic synthesis, and also display DNA-binding properties [17][18][19][20][21][22][23][24] etc. (Fig.…”

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confidence: 99%

Recent Advances in the Synthesis of Perimidines and their Applications

Sahiba¹,

Agarwal²

2020

Top Curr Chem (Z)

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Perimidines are versatile scaffolds and a fascinating class of N-heterocycles that have evolved significantly in recent years due to their immense applications in life sciences, medical sciences, and industrial chemistry. Their ability of molecular interaction with different proteins, complex formation with metals, and distinct behavior in various ranges of light makes them more appealing and challenging for future scientists. Various novel technologies have been developed for the selective synthesis of perimidines and their conjugated derivatives. These methods extend to the preparation of different bioactive and industrially applicable molecules. This review aims to present the most recent advancements in perimidine synthesis under varied conditions like MW radiation, ultrasound, and grinding using different catalysts such as ionic liquids, acid, metal, and nanocatalyst and also under green environments like catalyst and solvent-free synthesis. The applications of perimidine derivatives in drug discovery, polymer chemistry, photo sensors, dye industries, and catalytic activity in organic synthesis are discussed in this survey. This article is expected to be a systematic, authoritative, and critical review on the chemistry of perimidines that compiles most of the state-of-art innovation in this area.

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Discotic mesogens based on triphenylene-fused benzimidazole or perimidine: facile synthesis, mesomorphism, optical properties and self-assembly

Cited by 19 publications

References 63 publications

Novel Imidazole Liquid Crystals; Experimental and Computational Approaches

Novel Imidazole Liquid Crystals; Experimental and Computational Approaches

Solvent-Free Mechanochemical Synthesis of High Transition Biphenyltetracarboxydiimide Liquid Crystals

Recent Advances in the Synthesis of Perimidines and their Applications

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