Synthesis and phase transition behavior of calamitic liquid crystals containing heterocyclic core and lateral ethoxy substituent

Foo, Kok Leei; Ha, Sie‐Tiong; Yeap, Guan‐Yeow

doi:10.1080/01411594.2021.2023745

Cited by 5 publications

(5 citation statements)

References 53 publications

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“…The 1,3-benzothiazolyl framework is a constituent of several compounds that have been studied in a range of different areas, with focuses on their pharmacological activities [1][2][3][4][5][6][7][8][9], their applications in optical materials [10,11], their functions in liquid crystals [12], and their potential uses as agents in industrial processes [13]. Although these types of compounds exist naturally, they are rare [14].…”

Section: Introductionmentioning

confidence: 99%

Structural Study of N-(1,3-Benzothiazol-2-yl)-4-Halobenzenesulfonylhydrazides: Hirshfeld Surface Analysis and PIXEL Calculations

Gomes,

Low,

Pinheiro

et al. 2024

Crystals

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Hydrazonylsulfones such as Bt-NHNHSO2R and their iminotautomers have been studied as optical materials and for their biological potential. In this work, a structural study has been carried out on N-(1,3-benzothiazol-2-yl)-4-(halogenobenzenesulfonyl)-hydrazides (1: X = F, Cl, Br). For (1: X = F), single-crystal X-ray diffraction, Hirshfeld surface analysis, and PIXEL calculations were conducted, while in (1: X = Cl) and (1: X = Br), only single-crystal X-ray diffraction studies were successfully conducted due to the disordering of the solvent. Each compound crystallises with two independent but similar amino tautomers in the asymmetric units: compound (1: X = F) crystallises in the monoclinic P21/c, and the isostructural pair (X: 1 = Cl and Br) crystallises in the tetragonal P-421c space group. In the most stable motif of the supramolecular arrangement, the molecules of the asymmetric unit are connected by classical N–H(hydrazinyl)···N(thiazoyl) hydrogen bonds and several face-to-face, offset π···π interactions. This motif has a very powerful influence on the crystal structure due to its direct links with the other weaker motifs. Other significant intermolecular interactions found in the structure include N–H(hydrazonyl)···O(sulfonate) bonds. Analogous intermolecular interactions were found in similar compounds, leading to the conclusion that those interactions are the most important instabilizing the solid state of hydrazonylsulfones.

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Section: Introductionmentioning

confidence: 99%

Structural Study of N-(1,3-Benzothiazol-2-yl)-4-Halobenzenesulfonylhydrazides: Hirshfeld Surface Analysis and PIXEL Calculations

Gomes,

Low,

Pinheiro

et al. 2024

Crystals

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“…A para-substituted phenyl ring is used to confirm that the molecules have structural linearity and large molecular polarizability with respect to terminal and lateral side groups which further impact on the exhibition of liquid crystalline phase. 15 Till the date, different type of liquid crystalline compound based on chalcone group was reported in the literature with different types of mesogenic properties. [16][17][18][19][20][21] Apart from this, our research group reported two phenyl ring based linear and non-linear single chalcone substituted imidazolium based LCs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of acrylamide substituted sulfanilamide based calamitic LCs: effect of terminal group on phase behavior

Meena,

Sharma,

Mali

et al. 2024

10.5267/j.ccl

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In the present study, we have prepared two phenyl ring substituted sulfanilamide bearing acrylamide linking groups. The four derivatives (C1-C4) were prepared by changing the left n-alkoxy terminal group. The liquid crystalline properties of the synthesized sulfanilamide-based compounds were investigated using POM and DSC studies. All four materials exhibit nematic liquid crystalline properties during both heating and cooling. They also demonstrate a broad temperature range and thermal stability. Further, we have studied the structure-property relationship to gain a better understanding of the effect of the linking group and variable alkoxy tail group on mesomorphic behavior. The results indicate that thermal stability, mesophase temperature range, and liquid crystalline properties depend on the linking group and variable alkyl chain length.

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“…They are also important precursors of optical materials, e. g., as dyes, fluorescence probes, and for the detection of photo‐physical properties [1,3] . These compounds are also of interest for the study of liquid crystal properties [4] . They are also important precursors of optical materials, e. g., as dyes, fluorescence probes, and for the detection of photo‐physical properties [1,3] .…”

Section: Introductionmentioning

confidence: 99%

“…They are also important precursors of optical materials, e. g., as dyes, fluorescence probes, and for the detection of photo‐physical properties [1,3] . Their liquid crystal properties [4] are also of interest. Moreover, these scaffolds have been utilized in industry as antioxidants, vulcanization accelerators, chemo‐sensors for a range of analyses, as dopants in light‐emitting organic electroluminescent devices, fungicides in leather and paper production, corrosion inhibitors in antifreeze formulations, and ultraviolet (UV) light stabilizers in textiles and plastics [5] .…”

Section: Introductionmentioning

confidence: 99%

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Crystal structure of N‐(1,3‐benzothiazol‐2‐yl)‐4‐iodobenzene‐1‐sulfonohydrazide: the unexpected importance of l N‐H⋅⋅⋅π and I⋅⋅⋅π interactions on the supramolecular arrangement

Gomes

Früchtl

Low

et al. 2022

Zeitschrift anorg allge chemie

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The 2-hydrazinyl-1,3-benzothiazole derivatives are precursors for synthesis of several compounds of technological interest, including the BtÀ NHÀ N=CHR 1 (R 1 = alkyl, aryl, heteroaryl), derivatives. Usually when BtÀ NHÀ NH 2 is allowed to react with a benzenesulfonyl chloride the substitution is observed in the terminal nitrogen of the arenehydrazine unit, but when 4iodophenyl sulfonyl chloride (4-IC 6 H 4 SO 2 Cl) was used, the product isolated was the title compound as confirmed by Rxanalysis. Determination of the crystal structure revealed that the definition of the arrangement was driven by NÀ H•••π, CÀ I•••π and S2À O21•••π interactions instead of the classic O•••HÀ N hydrogen bonds. The interactions were confirmed by HS analysis. Interaction energy calculations showed that the π interactionsbased motifs play an important role in the supramolecular arrangement, contributing about 60 % to the total energy of the lattice. DFT calculations showed that the energy of the CÀ I•••π dimer is complemented with contributions of π•••π stacking and NÀ H•••π interaction between the primary amine and the thiazole aromatic ring.

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Synthesis and phase transition behavior of calamitic liquid crystals containing heterocyclic core and lateral ethoxy substituent

Cited by 5 publications

References 53 publications

Structural Study of N-(1,3-Benzothiazol-2-yl)-4-Halobenzenesulfonylhydrazides: Hirshfeld Surface Analysis and PIXEL Calculations

Structural Study of N-(1,3-Benzothiazol-2-yl)-4-Halobenzenesulfonylhydrazides: Hirshfeld Surface Analysis and PIXEL Calculations

Synthesis and characterization of acrylamide substituted sulfanilamide based calamitic LCs: effect of terminal group on phase behavior

Crystal structure of N‐(1,3‐benzothiazol‐2‐yl)‐4‐iodobenzene‐1‐sulfonohydrazide: the unexpected importance of l N‐H⋅⋅⋅π and I⋅⋅⋅π interactions on the supramolecular arrangement

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