Supramolecular hydrogen-bonded liquid crystals based on 4-n-alkylthiobenzoic acids and 4,4′-bipyridine: Their mesomorphic behavior with comparative study including alkyl and alkoxy counterparts

Arakawa, Yuki; Sasaki, Yukito; Tsuji, Hideto

doi:10.1016/j.molliq.2019.01.119

Cited by 45 publications

(32 citation statements)

References 65 publications

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“…Such at rend is ascribed to the more bent geometry and flexibility of thioether-containing dimers, [56] which is fundamentally in agreement with previousobservations for rodlike mesogens. [61][62][63][64][65] In addition, the phase transitions of dimers 1, 2,a nd 3 were compared with those of the corresponding cyanobiphenyl counterparts 8, 9,a nd 10,r espectively. We revisited the phasetransition behavior of 8 to obtain its cooling data.…”

Section: Resultsmentioning

confidence: 99%

Ether‐ and Thioether‐Linked Naphthalene‐Based Liquid‐Crystal Dimers: Influence of Chalcogen Linkage and Mesogenic‐Arm Symmetry on the Incidence and Stability of the Twist–Bend Nematic Phase

Arakawa

Ishida

Tsuji

2020

Chemistry A European J

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The twist–bend nematic (NTB) phase with a heliconical nanostructure of the local director generating symmetry breaking by achiral bent‐shaped molecules is a hot topic of current liquid‐crystal science. As opposed to the most common methylene‐linked dimers, this study demonstrates chalcogen ether‐ and/or thioether‐linked 6‐(4‐cyanophenyl)‐2‐naphthyl‐based liquid‐crystal dimers with symmetric and asymmetric π‐conjugated mesogenic‐arm structures that exhibit the NTB phase. Although the symmetric bis(ether)‐linked dimer exhibits only the conventional nematic (N) phase, the asymmetric bis(ether)‐linked dimer can form the NTB phase. All thioether‐linked dimers form the NTB phase, wherein the dimers with asymmetric arms vitrify in the NTB phase on cooling to room temperature. The phase transitions are discussed in terms of the chalcogen linkage combination, mesogenic‐arm symmetry, and spacer length. It is revealed that thioether‐linked dimers based on asymmetric π‐conjugated mesogenic arms with terminal cyano groups are highly beneficial for the realization of materials that form a wide range of NTB phases and glassy NTB states at room temperature.

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Section: Resultsmentioning

confidence: 99%

Ether‐ and Thioether‐Linked Naphthalene‐Based Liquid‐Crystal Dimers: Influence of Chalcogen Linkage and Mesogenic‐Arm Symmetry on the Incidence and Stability of the Twist–Bend Nematic Phase

Arakawa

Ishida

Tsuji

2020

Chemistry A European J

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“…Recently, density functional theory (DFT) becomes an essential routine method to correlate the outcome theoretical parameters with the experimental findings [38][39][40][41]. Several H-bonded mesogenic complexes containing azo, ester, and Schiff base central linkages have been widely reported [42][43][44][45][46][47]. Most of them are based on the linear intermolecular H-bonding interactions [48][49][50][51][52][53], and there are an attractive area of interest toward the formation of nonlinear SMHBLCs [54][55][56].…”

Section: Introductionmentioning

confidence: 99%

Chair- and V-Shaped of H-bonded Supramolecular Complexes of Azophenyl Nicotinate Derivatives; Mesomorphic and DFT Molecular Geometry Aspects

et al. 2020

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New geometrical architectures of chair- and V-shaped supramolecular liquid crystalline complexes were molded through 1:1 intermolecular hydrogen bonding interactions between 4-(4-(hexyloxy)phenylazo)methyl)phenyl nicotinate and 4-alkoxybenzoic acids. The length of terminal alkoxy acid chains varied, n = 6 to 16 carbons. The mesomorphic behaviour of these complexes was examined through differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). Fourier-transform infrared spectroscopy (FT-IR) was carried out to confirm the presence of Fermi bands that appeared for the hydrogen bonding formation. Enantiotropic nematic phases were observed and covered all lengths of alkoxy chains. The geometrical structures of the prepared supramolecular complexes geometries were estimated by Density functional theory (DFT) calculations. The supramolecular complexes I/An are projected to exhibit a nonlinear geometry with V-shaped and chair-shaped geometry. The chair-shaped conformers of I/An were found to be more stable than V-shaped isomeric complexes. Moreover, the effect of the change of the mesogenic core on the mesophase thermal stability (TC) has been investigated by a comparative study of the present azo supramolecular H-bonding LCs (SMHBCs) I/An and our previously reported their Schiff base analogue complexes, II/An. The findings of the DFT illustrated the high impact of CH=N as a mesogenic core on the mesomorphic behavior in terms of the competitive lateral and terminal intermolecular interactions as well as the molecular electrostatic potential (MEP).

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“…14,15 Many Schiff bases with a low molar mass have been synthesized and investigated extensively for applications with liquid crystals. [16][17][18][19] Generally, stability of a mesophase depends on the polarity and/or polarizability of the central part of the molecule. High demands of new SMHBLC complexes for applications has led to the preparation and study of numerous mesogens, particularly thermotropic liquid crystals.…”

Section: Introductionmentioning

confidence: 99%

“…[20][21][22][23] Several mesogenic homologous series containing ester/Schiff base central linkages have been widely reported. 16,18,19,[24][25][26] Most of the H-bonded mesogens studied are based on rod-like intermolecular Hbonding [20][21][22][23]27,28 and there is an increasing interest for forming angular SMHBLCs through intermolecular hydrogen-bond formation. 29,30 Nowadays, designing materials according to computational prediction also has attracted high interest.…”

Section: Introductionmentioning

confidence: 99%

New chair shaped supramolecular complexes-based aryl nicotinate derivative; mesomorphic properties and DFT molecular geometry

2019

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Supramolecular hydrogen-bonded liquid crystals based on 4-n-alkylthiobenzoic acids and 4,4′-bipyridine: Their mesomorphic behavior with comparative study including alkyl and alkoxy counterparts

Cited by 45 publications

References 65 publications

Ether‐ and Thioether‐Linked Naphthalene‐Based Liquid‐Crystal Dimers: Influence of Chalcogen Linkage and Mesogenic‐Arm Symmetry on the Incidence and Stability of the Twist–Bend Nematic Phase

Ether‐ and Thioether‐Linked Naphthalene‐Based Liquid‐Crystal Dimers: Influence of Chalcogen Linkage and Mesogenic‐Arm Symmetry on the Incidence and Stability of the Twist–Bend Nematic Phase

Chair- and V-Shaped of H-bonded Supramolecular Complexes of Azophenyl Nicotinate Derivatives; Mesomorphic and DFT Molecular Geometry Aspects

New chair shaped supramolecular complexes-based aryl nicotinate derivative; mesomorphic properties and DFT molecular geometry

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