Ferroelectrically Switching Helical Columnar Assembly Comprising <i>Cisoid</i> Conformers of a 1,2,3‐Triazole‐based Liquid Crystal

Nguyen, Manh Linh; Byun, Jaeduk; Kim, Suwoong; Hyun, June Won; Hur, Kahyun; Shin, Tae Joo; Cho, Byoung‐Ki

doi:10.1002/anie.201813195

Cited by 22 publications

(15 citation statements)

References 41 publications

(16 reference statements)

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“…The synthetic procedures of the LC molecules are described in Schemes S1 and S2, and their 1 H and 13 C NMR data are consistent with the designed molecular structures (Figures S1 and S2). The thermal properties of two LCs (1 and 2) were characterized by differential scanning calorimetry (DSC) and polarized optical microscopy (POM).…”

Section: ■ Results and Discussionmentioning

confidence: 53%

“…Columnar LCs based on 1,2,3-triazolyl linkers, known as amide surrogates, have recently shown helical assemblies 12,13 and E-field response. 13−15 Similar to an amide group, this heterocycle is polar (dipole moment, 4.55 debyes) 16−18 and capable of 1D hydrogen-bonding (H-bonding) owing to its asymmetric shape and ambivalent character.…”

Section: ■ Introductionmentioning

confidence: 99%

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The Role of the 1,2,3-Triazolyl Heterocycle in the Helical Columnar Assembly and Electric Field Response

2021

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Here, we have proven the role of the 1,2,3-triazolyl group in the helical assembly and electric field (E-field) response upon comparing liquid crystal analogs 1 and 2 based on 1,2,3triazolyl and 1,3,4-oxadiazolyl linkers, respectively. An ordered helical column was only observed in 1, driven by the hydrogen-bonding interactions between the adjacent triazolyl nitrogen and hydrogen atoms. X-ray diffraction and energy simulations indicate that the helical column is a 11 2 helix and the helical axis does not coincide with the center of the molecular long axis. The key for the formation of the helical column is the tilted conformation of 1 originating from the steric repulsion between the triazolyl C−H and C−H of the aromatic core. Analysis of the dynamics in the simple hexagonal columnar phase revealed that the in-plane rotational motion of the triazolyl linker (1) is allowed, while the oxadiazolyl linker of 2 has limited conformational flexibility. A uniform alignment under an E-field only occurs in 1, demonstrating the requirement for conformational flexibility in the polar linker. This alignment enhances the electric conductance of 1 by approximately two-fold.

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Section: ■ Results and Discussionmentioning

confidence: 53%

Section: ■ Introductionmentioning

confidence: 99%

The Role of the 1,2,3-Triazolyl Heterocycle in the Helical Columnar Assembly and Electric Field Response

2021

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“…Nevertheless, its ferroelectric property had not been investigated until recently. In 2019, Cho's group reported for the first time a naphthalene‐based LC with 1,2,3‐triazolyl linkages ( 15 ; Figure a) . This compound exhibited a helical columnar LC (Col hel ) phase with hexagonal symmetry for temperatures ranging from 63.3 to 118.5 °C.…”

Section: Columnar Lcs With 123‐triazolyl Groupsmentioning

confidence: 99%

Ferroelectrically Switchable Axial Polarization in Columnar Liquid Crystalline Phases

Nguyen

Cho

2020

Chemistry A European J

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Recently, ferroelectrically switchable columnar LCs have drawn a great deal of attention for their generation of rich polarization domains. Because of their unique dielectric and self‐assembly properties, they are considered to be a promising material for the design of sensors and ultra‐high memory devices. Herein, ferroelectrically switchable LCs by using ester, amide, and 1,2,3‐triazole groups are reviewed. Most of them do not exhibit genuine ferroelectricity owing to the low energy barrier between the two polar states. The intermolecular interactions between polar groups strongly affect the switchability and stability of polarization. Therefore, it is challenging to balance these two competing factors to improve the ferroelectric function in columnar LCs. Overall, additional effort, including LC design and device fabrication, should be made to optimize the material performance for practical applications in the future.

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“…Herein, we focused on the π-planar tetraphenylporphyrin derivative ( 1 ) bearing four −CONHC 14 H 29 chains, whose molecular assembly structure and ferroelectric response were discussed. Although the preparation of molecule 1 has already been reported by Shi et al, − the application of a photovoltaic cell was attempted by Liu et al However, both the dielectric and/or ferroelectric responses of the N–H···O hydrogen-bonding molecular assembly of 1 have unfortunately not yet been examined. The dynamic behavior of the N–H···O amide-type hydrogen-bonding interaction enables the design of new ferroelectrics based on an optically interesting porphyrin π core.…”

Section: Introductionmentioning

confidence: 99%

Ferroelectricity of a Tetraphenylporphyrin Derivative Bearing −CONHC₁₄H₂₉ Chains at 500 K

Takeda

Hoshino

et al. 2019

J. Phys. Chem. C

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Optical properties of porphyrin derivatives were used to fabricate an artificial light-harvesting system. The introduction of a N−H•••O hydrogen-bonding alkylamide chain (−CONHC n H 2n+1 ) into a functional π-system is among the useful approaches to design multifunctional supramolecular assemblies. The tetraphenylporphyrin derivative bearing four −CONHC 14 H 29 chains (1) shows the successive and reversible phase transition behavior of S1−S2 at 338 K, S2−Col r at 444 K, and Col r −I (isotropic liquid) at 564 K, where a fluidic discotic rectangular columnar (Col r ) liquid crystal phase was observed in a wide temperature range of 444−564 K before melting. The one-dimensional columnar molecular assembly of (1) ∞ was constructed using a simultaneous operation of N−H•••O hydrogen-bonding and π-stacking interactions. Temperature (T)and frequency (f)-dependent dielectric constants of 1 indicated characteristic dielectric enhancement at higher-T and lower-f conditions above 500 K because of the thermally activated motional freedom of the polar N−H•••O hydrogen-bonding unit in the Col r phase. The polarization−electric field (P−E) curves at f = 0.1 Hz clearly indicated ferroelectric hysteresis behavior with a remanent polarization (P r ) of 1 μC cm −2 and a coercive electric field (E c ) of 2 V μm −1 at 503 K. The stable operation of the high-T ferroelectrics at approximately 500 K facilitates the potential application of a memory device in a high-T environment.

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Ferroelectrically Switching Helical Columnar Assembly Comprising Cisoid Conformers of a 1,2,3‐Triazole‐based Liquid Crystal

Cited by 22 publications

References 41 publications

The Role of the 1,2,3-Triazolyl Heterocycle in the Helical Columnar Assembly and Electric Field Response

The Role of the 1,2,3-Triazolyl Heterocycle in the Helical Columnar Assembly and Electric Field Response

Ferroelectrically Switchable Axial Polarization in Columnar Liquid Crystalline Phases

Ferroelectricity of a Tetraphenylporphyrin Derivative Bearing −CONHC₁₄H₂₉ Chains at 500 K

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Ferroelectrically Switching Helical Columnar Assembly Comprising Cisoid Conformers of a 1,2,3‐Triazole‐based Liquid Crystal

Cited by 22 publications

References 41 publications

The Role of the 1,2,3-Triazolyl Heterocycle in the Helical Columnar Assembly and Electric Field Response

The Role of the 1,2,3-Triazolyl Heterocycle in the Helical Columnar Assembly and Electric Field Response

Ferroelectrically Switchable Axial Polarization in Columnar Liquid Crystalline Phases

Ferroelectricity of a Tetraphenylporphyrin Derivative Bearing −CONHC14H29 Chains at 500 K

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Ferroelectricity of a Tetraphenylporphyrin Derivative Bearing −CONHC₁₄H₂₉ Chains at 500 K