Electron-deficient acene-based liquid crystals: Dialkoxydicyanopyrazinoquinoxalines

Takashi Takeda; Jun'ya Tsutsumi; Tatsuo Hasegawa; Shin Ichiro Noro; Takayoshi Nakamura; Tomoyuki Akutagawa

doi:10.1039/c5tc00022j

Electron-deficient acene-based liquid crystals: Dialkoxydicyanopyrazinoquinoxalines

Takashi Takeda, Jun'ya Tsutsumi, Tatsuo Hasegawa, Shin Ichiro Noro, Takayoshi Nakamura, Tomoyuki Akutagawa

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

Three electron-accepting dialkoxydicyanopyrazinoquinoxaline derivatives (1a, 1b, and 1c) showed properties of smectic (Sm) liquid crystals. Temperature-dependent X-ray diffraction studies were consistent with the formation of a bilayer structure through the π-overlap and interdigitation of alkoxy chains in the Sm liquid crystalline state. Intermolecular dipole-dipole interactions between the cyano groups played an important role in stabilizing the bilayer structure and liquid crystalline properties. Elongation of the alkoxy chains from C₆H₁₃O- (1a) and/or C₁₂H₂₅O- (1b) to C₁₈H₃₇O- (1c) changed the molecular arrangements and the liquid crystal phase from SmA to SmC, suggesting the importance of the van der Waals interaction of C_nH_2n+1O- chains for stabilizing the liquid crystalline phase. A hole-mobility value of 5 × 10^-3 cm² V^-1 s^-1 was observed for the SmA phase of 1b at 438 K based on transient photocurrent measurements.

Original language	English
Pages (from-to)	3016-3022
Number of pages	7
Journal	Journal of Materials Chemistry C
Volume	3
Issue number	13
DOIs	https://doi.org/10.1039/c5tc00022j
Publication status	Published - 2015 Apr 7

ASJC Scopus subject areas

Chemistry(all)
Materials Chemistry

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title = "Electron-deficient acene-based liquid crystals: Dialkoxydicyanopyrazinoquinoxalines",

abstract = "Three electron-accepting dialkoxydicyanopyrazinoquinoxaline derivatives (1a, 1b, and 1c) showed properties of smectic (Sm) liquid crystals. Temperature-dependent X-ray diffraction studies were consistent with the formation of a bilayer structure through the π-overlap and interdigitation of alkoxy chains in the Sm liquid crystalline state. Intermolecular dipole-dipole interactions between the cyano groups played an important role in stabilizing the bilayer structure and liquid crystalline properties. Elongation of the alkoxy chains from C6H13O- (1a) and/or C12H25O- (1b) to C18H37O- (1c) changed the molecular arrangements and the liquid crystal phase from SmA to SmC, suggesting the importance of the van der Waals interaction of CnH2n+1O- chains for stabilizing the liquid crystalline phase. A hole-mobility value of 5 × 10-3 cm2 V-1 s-1 was observed for the SmA phase of 1b at 438 K based on transient photocurrent measurements.",

author = "Takashi Takeda and Jun'ya Tsutsumi and Tatsuo Hasegawa and Noro, {Shin Ichiro} and Takayoshi Nakamura and Tomoyuki Akutagawa",

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doi = "10.1039/c5tc00022j",

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T2 - Dialkoxydicyanopyrazinoquinoxalines

AU - Takeda, Takashi

AU - Tsutsumi, Jun'ya

AU - Hasegawa, Tatsuo

AU - Noro, Shin Ichiro

AU - Nakamura, Takayoshi

AU - Akutagawa, Tomoyuki

PY - 2015/4/7

Y1 - 2015/4/7

N2 - Three electron-accepting dialkoxydicyanopyrazinoquinoxaline derivatives (1a, 1b, and 1c) showed properties of smectic (Sm) liquid crystals. Temperature-dependent X-ray diffraction studies were consistent with the formation of a bilayer structure through the π-overlap and interdigitation of alkoxy chains in the Sm liquid crystalline state. Intermolecular dipole-dipole interactions between the cyano groups played an important role in stabilizing the bilayer structure and liquid crystalline properties. Elongation of the alkoxy chains from C6H13O- (1a) and/or C12H25O- (1b) to C18H37O- (1c) changed the molecular arrangements and the liquid crystal phase from SmA to SmC, suggesting the importance of the van der Waals interaction of CnH2n+1O- chains for stabilizing the liquid crystalline phase. A hole-mobility value of 5 × 10-3 cm2 V-1 s-1 was observed for the SmA phase of 1b at 438 K based on transient photocurrent measurements.

AB - Three electron-accepting dialkoxydicyanopyrazinoquinoxaline derivatives (1a, 1b, and 1c) showed properties of smectic (Sm) liquid crystals. Temperature-dependent X-ray diffraction studies were consistent with the formation of a bilayer structure through the π-overlap and interdigitation of alkoxy chains in the Sm liquid crystalline state. Intermolecular dipole-dipole interactions between the cyano groups played an important role in stabilizing the bilayer structure and liquid crystalline properties. Elongation of the alkoxy chains from C6H13O- (1a) and/or C12H25O- (1b) to C18H37O- (1c) changed the molecular arrangements and the liquid crystal phase from SmA to SmC, suggesting the importance of the van der Waals interaction of CnH2n+1O- chains for stabilizing the liquid crystalline phase. A hole-mobility value of 5 × 10-3 cm2 V-1 s-1 was observed for the SmA phase of 1b at 438 K based on transient photocurrent measurements.

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Electron-deficient acene-based liquid crystals: Dialkoxydicyanopyrazinoquinoxalines

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