Photochemical control of helical pitch of glass-forming dimeric cholesteric liquid crystals by isomerization of embedded di-mesogenic compounds with both cholesterol and azobenzene groups

Nobuyuki Tamaoki, Yasuyuki Aoki, Masaya Moriyama, Masatoshi Kidowaki

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

We synthesized di-mesogenic liquid crystals with both cholesterol and azobenzene groups by esterification of 10,12-docosadiynedioic acid or docosanedioic acid with 4-alkyl-4′-hydroxyazobenzene (or 4-hydroxyazobenzene) and cholesterol. Two compounds without an alkyl chain on the azobenzene unit show cholesteric and smectic phases, while five compounds with an alkyl chain from butyl to hexadecyl show only a smectic phase. When the compounds were doped in 2-10 w% to a dicholesteryl ester forming stable cholesteric glass, the mixture became photo-responsive. Upon irradiation at 366 nm, the cholesteric band of the mixtures shifted toward shorter wavelength caused by the photo-isomerization from trans to cis of the azobenzene unit on the dopant. The extent of the shift depends on irradiation energy, temperature and the length of the alkyl chain on the azobenzene unit. When a thin film of the dicholesteryl compounds containing 5w% of the dopant having a heptyl substituent on the azobenzene unit was irradiated at 90°C, the reflection band shifted from 730 nm (infrared) to 490 nm (blue). The mixture went into the glassy state keeping the shifted cholesteric reflection band after rapid cooling from the liquid crystalline temperature to 0°C. The cholesteric glassy state was stable up to 80°C. Since the molecular arrangement of the dicholesteryl compound and the conformation of the doped azobenzene derivatives completely returned to the initial state upon reheating to isotropic temperature, the photo-responsibility and glass-forming property of the mixture is applicable to full-color rewritable recording materials.

Original languageEnglish
Title of host publicationProceedings of SPIE - The International Society for Optical Engineering
EditorsI.C. Khoo
Pages103-112
Number of pages10
Volume4799
DOIs
Publication statusPublished - 2002
Externally publishedYes
EventLiquid Crystals VI - Seattle, WA, United States
Duration: 2002 Jul 82002 Jul 9

Other

OtherLiquid Crystals VI
CountryUnited States
CitySeattle, WA
Period02/7/802/7/9

Fingerprint

Cholesteric liquid crystals
Azobenzene
Cholesterol
cholesterol
Isomerization
isomerization
liquid crystals
Glass
glass
acids
irradiation
Doping (additives)
Irradiation
temperature
Photoisomerization
esters
Acids
recording
Esterification
color

Keywords

  • Azobenzene
  • Cholesteric liquid crystal
  • Glass
  • Photoisomerization
  • Recording material

ASJC Scopus subject areas

  • Electrical and Electronic Engineering
  • Condensed Matter Physics

Cite this

Tamaoki, N., Aoki, Y., Moriyama, M., & Kidowaki, M. (2002). Photochemical control of helical pitch of glass-forming dimeric cholesteric liquid crystals by isomerization of embedded di-mesogenic compounds with both cholesterol and azobenzene groups. In I. C. Khoo (Ed.), Proceedings of SPIE - The International Society for Optical Engineering (Vol. 4799, pp. 103-112) https://doi.org/10.1117/12.453260

Photochemical control of helical pitch of glass-forming dimeric cholesteric liquid crystals by isomerization of embedded di-mesogenic compounds with both cholesterol and azobenzene groups. / Tamaoki, Nobuyuki; Aoki, Yasuyuki; Moriyama, Masaya; Kidowaki, Masatoshi.

Proceedings of SPIE - The International Society for Optical Engineering. ed. / I.C. Khoo. Vol. 4799 2002. p. 103-112.

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Tamaoki, N, Aoki, Y, Moriyama, M & Kidowaki, M 2002, Photochemical control of helical pitch of glass-forming dimeric cholesteric liquid crystals by isomerization of embedded di-mesogenic compounds with both cholesterol and azobenzene groups. in IC Khoo (ed.), Proceedings of SPIE - The International Society for Optical Engineering. vol. 4799, pp. 103-112, Liquid Crystals VI, Seattle, WA, United States, 02/7/8. https://doi.org/10.1117/12.453260
Tamaoki, Nobuyuki ; Aoki, Yasuyuki ; Moriyama, Masaya ; Kidowaki, Masatoshi. / Photochemical control of helical pitch of glass-forming dimeric cholesteric liquid crystals by isomerization of embedded di-mesogenic compounds with both cholesterol and azobenzene groups. Proceedings of SPIE - The International Society for Optical Engineering. editor / I.C. Khoo. Vol. 4799 2002. pp. 103-112
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abstract = "We synthesized di-mesogenic liquid crystals with both cholesterol and azobenzene groups by esterification of 10,12-docosadiynedioic acid or docosanedioic acid with 4-alkyl-4′-hydroxyazobenzene (or 4-hydroxyazobenzene) and cholesterol. Two compounds without an alkyl chain on the azobenzene unit show cholesteric and smectic phases, while five compounds with an alkyl chain from butyl to hexadecyl show only a smectic phase. When the compounds were doped in 2-10 w{\%} to a dicholesteryl ester forming stable cholesteric glass, the mixture became photo-responsive. Upon irradiation at 366 nm, the cholesteric band of the mixtures shifted toward shorter wavelength caused by the photo-isomerization from trans to cis of the azobenzene unit on the dopant. The extent of the shift depends on irradiation energy, temperature and the length of the alkyl chain on the azobenzene unit. When a thin film of the dicholesteryl compounds containing 5w{\%} of the dopant having a heptyl substituent on the azobenzene unit was irradiated at 90°C, the reflection band shifted from 730 nm (infrared) to 490 nm (blue). The mixture went into the glassy state keeping the shifted cholesteric reflection band after rapid cooling from the liquid crystalline temperature to 0°C. The cholesteric glassy state was stable up to 80°C. Since the molecular arrangement of the dicholesteryl compound and the conformation of the doped azobenzene derivatives completely returned to the initial state upon reheating to isotropic temperature, the photo-responsibility and glass-forming property of the mixture is applicable to full-color rewritable recording materials.",
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AB - We synthesized di-mesogenic liquid crystals with both cholesterol and azobenzene groups by esterification of 10,12-docosadiynedioic acid or docosanedioic acid with 4-alkyl-4′-hydroxyazobenzene (or 4-hydroxyazobenzene) and cholesterol. Two compounds without an alkyl chain on the azobenzene unit show cholesteric and smectic phases, while five compounds with an alkyl chain from butyl to hexadecyl show only a smectic phase. When the compounds were doped in 2-10 w% to a dicholesteryl ester forming stable cholesteric glass, the mixture became photo-responsive. Upon irradiation at 366 nm, the cholesteric band of the mixtures shifted toward shorter wavelength caused by the photo-isomerization from trans to cis of the azobenzene unit on the dopant. The extent of the shift depends on irradiation energy, temperature and the length of the alkyl chain on the azobenzene unit. When a thin film of the dicholesteryl compounds containing 5w% of the dopant having a heptyl substituent on the azobenzene unit was irradiated at 90°C, the reflection band shifted from 730 nm (infrared) to 490 nm (blue). The mixture went into the glassy state keeping the shifted cholesteric reflection band after rapid cooling from the liquid crystalline temperature to 0°C. The cholesteric glassy state was stable up to 80°C. Since the molecular arrangement of the dicholesteryl compound and the conformation of the doped azobenzene derivatives completely returned to the initial state upon reheating to isotropic temperature, the photo-responsibility and glass-forming property of the mixture is applicable to full-color rewritable recording materials.

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