Broad temperature range of cubic blue phase present in simple binary mixture systems containing rodlike Schiff base mesogens with tolane moiety

Huang, Chiung-Cheng; Chen, Yuhao; Chen, Sheng-Yen; Sun, Yizeng; Wu, Zong-Ye; Yu, Mei‐Ching; Chen, Bo‐Hao; Hsu, I‐Jui; Li, Wu; Lee, Jey‐Jau

doi:10.1039/c5sm02920a

Cited by 12 publications

(10 citation statements)

References 45 publications

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“…Most reports have been focused on Schiff bases since the discovery of nematogenic 4-methoxybenzylidene-4′-butylaniline at room temperature [37]. Recently, several thermotropic Schiff base liquid crystals based on two rings were documented [32,[38][39][40][41][42][43][44][45][46][47].…”

Section: Introductionmentioning

confidence: 99%

New Nitro-Laterally Substituted Azomethine Derivatives; Synthesis, Mesomorphic and Computational Characterizations

et al. 2021

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Two new homologues series, based on two rings of the azomethine central group bearing the terminal alkoxy group of various chain lengths, were prepared. The alkoxy chain length varied between 6 and 16 carbons. The other terminal wing in the first series was the F atom, and the compound is named N-4-florobenzylidene-4-(alkoxy)benzenamine (In). The second group of compounds included a lateral NO2 substituent in addition to the terminal F atom, named N-(4-fluoro-3-nitrobenzylidene)-4-(alkyloxy)aniline (IIn). Mesomorphic and optical properties were carried out via differential scanning calorimetry (DSC) and polarized optical microscopy (POM). Elemental analyses, FT-IR, and NMR spectroscopy were carried out to elucidate the molecular structures of the synthesized groups. Mesomorphic investigations indicated that all the synthesized homologues (In) were monomorphic, possessing the smectic A (SmA) phase monotropically, while the second group (IIn) members were non-mesomorphic. The experimental data indicated that the formation of the mesophase is affected by the protrusion of the lateral nitro group. The disruption of the mesophase in the second group was attributed to the increase of its molecular width, which affects its lateral intermolecular interactions. The computational simulations were in agreement with the experimental data. On the other hand, the location of NO2 group within the molecular geometry increased the melting temperature of the molecule, and thus, affected their thermal and physical properties. By discussing the estimated parameters, it was found that the molecular architecture, the dipole moment, and the polarizability of the investigated compounds are highly affected by the electronic nature and position of the terminal and lateral substituents as well as their volumes.

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Section: Introductionmentioning

confidence: 99%

New Nitro-Laterally Substituted Azomethine Derivatives; Synthesis, Mesomorphic and Computational Characterizations

et al. 2021

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“…1-Ethynyl-4-(alkyloxy)benzene and 1-ethynyl-4-alkylbenzene were synthesized according to the procedure mentioned in the literature. The intermediates, compounds c , and 4-(1-methylheptoxy)aniline were synthesized by our currently reported method . In addition, compounds OH-TI 7 and H-TI 7 have been prepared and characterized according to our previously reported method.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…All density functional theory (DFT) calculations were performed in the Gaussian09 package . The calculation strategy is based on our previous report . The coordinates used for geometry optimization of all Schiff base compounds were initially built in the Avogadro program and then optimized by long-range-corrected hybrid functional CAM-B3LYP in the G09 program.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…However, only a few racemic rodlike Schiff base molecules were utilized to induce BPs. Recently, we prepared a series of chiral and racemic rodlike Schiff base mesogens with tolane moiety . Notably, they possess two specific soft crystal phases that could be confirmed by the polarized optical microscopy (POM) texture and variable-temperature X-ray diffraction (XRD).…”

Section: Introductionmentioning

confidence: 97%

“…Recently, we prepared a series of chiral and racemic rodlike Schiff base mesogens with tolane moiety. 35 Notably, they possess two specific soft crystal phases that could be confirmed by the polarized optical microscopy (POM) texture and variable-temperature X-ray diffraction (XRD). Additionally, they could be applied in the stabilization of the BP temperature range by adding chiral dopant ISO(6OBA) 2 , S811, or R811.…”

Section: Introductionmentioning

confidence: 99%

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Effect of the Functional Groups of Racemic Rodlike Schiff Base Mesogens on the Stabilization of Blue Phase in Binary Mixture Systems

Huang

Sie

et al. 2016

J. Phys. Chem. B

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Four series of rodlike racemic Schiff base mesogens possessing different alkyl chains and two types of linkages, ester and alkynyl linkages, were synthesized and applied to induce cubic blue phases (BPs) in simple binary mixture systems. The mesophases of these Schiff base mesogens were confirmed by variable-temperature X-ray diffraction and the characteristic texture from polarized optical microscopy (POM). In general, when chiral additive S-(+)-2-octyl 4-(4-hexyloxybenzoyloxy)benzoate (S811; 20-40 wt %) is added into the rodlike racemic salicylaldimine-based mesogens, the cubic BPs could be observed and its temperature range is larger than 20 K. The widest temperature range of the cubic BP (35 K) can be observed in the blending mixture composed of rodlike racemic salicylaldimine-based mesogen OH-TI possessing alkynyl linkage and 35-40 wt % S811. However, Schiff base mesogens possessing alkynyl linkage show a direct isotropic to chiral nematic transition when equal amount of chiral dopant is added. Notably, the termination temperature of BPs is very close to room temperature (ca. 35 °C) after 40.0 wt % S811 is added into the salicylaldimine-based mesogens possessing terminal alkyl chains and ester linkage. Interestingly, wide BPs (>30 K) can also be induced by adding chiral additive 1,4:3,6-dianhydro-2,5-bis[4-(n-hexyl-1-oxy)benzoic acid]sorbitol (ISO(6OBA)) with a high helical twisting power into the racemic Schiff base mesogen possessing ester linkage. Cubic BPI and BPII can be confirmed by reflectance spectra and POM. The results of reflectance spectra indicate that the binary mixture composed of salicylaldimine-based mesogens and S811 easily exhibits a supercooling effect and induces BPI. However, only BPII can be observed in all binary mixtures containing Schiff base mesogens. On the basis of our experimental results and molecular modeling, we suppose that the values of biaxiality, polarizability, and the dipole moment of molecular geometry are the main factors that affect BP stabilization.

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Tailoring tail-free nematogen of ethynylated-schiff base and its evaluation as solution-processable OLED emitting material

Lim

Rahamathullah

Sarih

et al. 2018

Journal of Luminescence

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Broad temperature range of cubic blue phase present in simple binary mixture systems containing rodlike Schiff base mesogens with tolane moiety

Cited by 12 publications

References 45 publications

New Nitro-Laterally Substituted Azomethine Derivatives; Synthesis, Mesomorphic and Computational Characterizations

New Nitro-Laterally Substituted Azomethine Derivatives; Synthesis, Mesomorphic and Computational Characterizations

Effect of the Functional Groups of Racemic Rodlike Schiff Base Mesogens on the Stabilization of Blue Phase in Binary Mixture Systems

Tailoring tail-free nematogen of ethynylated-schiff base and its evaluation as solution-processable OLED emitting material

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