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Photoswitching of Dihydroazulene Derivatives in Liquid-Crystalline Host Systems

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Photoswitching of Dihydroazulene Derivatives in Liquid-Crystalline Host Systems. / Petersen, Anne Ugleholdt; Jevric, Martyn; Mandle, Richard J; Sims, Mark T; Moore, John N; Cowling, Stephen J; Goodby, John W; Nielsen, Mogens Brøndsted.

In: Chemistry : A European Journal, Vol. 23, No. 21, 11.04.2017, p. 5090-5103.

Research output: Contribution to journalArticlepeer-review

Harvard

Petersen, AU, Jevric, M, Mandle, RJ, Sims, MT, Moore, JN, Cowling, SJ, Goodby, JW & Nielsen, MB 2017, 'Photoswitching of Dihydroazulene Derivatives in Liquid-Crystalline Host Systems', Chemistry : A European Journal, vol. 23, no. 21, pp. 5090-5103. https://doi.org/10.1002/chem.201700055

APA

Petersen, A. U., Jevric, M., Mandle, R. J., Sims, M. T., Moore, J. N., Cowling, S. J., Goodby, J. W., & Nielsen, M. B. (2017). Photoswitching of Dihydroazulene Derivatives in Liquid-Crystalline Host Systems. Chemistry : A European Journal, 23(21), 5090-5103. https://doi.org/10.1002/chem.201700055

Vancouver

Petersen AU, Jevric M, Mandle RJ, Sims MT, Moore JN, Cowling SJ et al. Photoswitching of Dihydroazulene Derivatives in Liquid-Crystalline Host Systems. Chemistry : A European Journal. 2017 Apr 11;23(21):5090-5103. https://doi.org/10.1002/chem.201700055

Author

Petersen, Anne Ugleholdt ; Jevric, Martyn ; Mandle, Richard J ; Sims, Mark T ; Moore, John N ; Cowling, Stephen J ; Goodby, John W ; Nielsen, Mogens Brøndsted. / Photoswitching of Dihydroazulene Derivatives in Liquid-Crystalline Host Systems. In: Chemistry : A European Journal. 2017 ; Vol. 23, No. 21. pp. 5090-5103.

Bibtex - Download

@article{85737297d8d84ce3ba78764dae7c18a7,
title = "Photoswitching of Dihydroazulene Derivatives in Liquid-Crystalline Host Systems",
abstract = "Photoswitches and dyes in the liquid-crystalline nematic phase have the potential for use in a wide range of applications. A large order parameter is desirable to maximize the change in properties induced by an external stimulus. A set of photochromic and nonphotochromic dyes were investigated for these applications. It was found that a bent-shaped 7-substituted dihydroazulene (DHA) photoswitch exhibited liquid-crystalline properties. Further investigation demonstrated that this material actually followed two distinct reaction pathways on heating, to a deactivated form by a 1,5-sigmatropic shift and to a linear 6-substituted DHA. In addition, elimination of hydrogen cyanide from the photoactive DHA gave both bent and linear azulene dyes. In a nematic host that has no absorbance around 350 nm, it was found that only the linear DHA derivative has nematic properties; however, both 6- and 7-substituted DHAs were found to have large order parameters. In the nematic host, ring opening of either DHA to the corresponding vinylheptafulvene resulted in a decrease in dichroic order parameter and an unusually fast back-reaction to a mixture of both DHAs. Likewise, only the linear azulene derivative showed mesomorphic properties. In the same nematic host, large order parameters were also observed for these dyes.",
keywords = "Journal Article",
author = "Petersen, {Anne Ugleholdt} and Martyn Jevric and Mandle, {Richard J} and Sims, {Mark T} and Moore, {John N} and Cowling, {Stephen J} and Goodby, {John W} and Nielsen, {Mogens Br{\o}ndsted}",
note = "{\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",
year = "2017",
month = apr,
day = "11",
doi = "10.1002/chem.201700055",
language = "English",
volume = "23",
pages = "5090--5103",
journal = "Chemistry : A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "21",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Photoswitching of Dihydroazulene Derivatives in Liquid-Crystalline Host Systems

AU - Petersen, Anne Ugleholdt

AU - Jevric, Martyn

AU - Mandle, Richard J

AU - Sims, Mark T

AU - Moore, John N

AU - Cowling, Stephen J

AU - Goodby, John W

AU - Nielsen, Mogens Brøndsted

N1 - © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2017/4/11

Y1 - 2017/4/11

N2 - Photoswitches and dyes in the liquid-crystalline nematic phase have the potential for use in a wide range of applications. A large order parameter is desirable to maximize the change in properties induced by an external stimulus. A set of photochromic and nonphotochromic dyes were investigated for these applications. It was found that a bent-shaped 7-substituted dihydroazulene (DHA) photoswitch exhibited liquid-crystalline properties. Further investigation demonstrated that this material actually followed two distinct reaction pathways on heating, to a deactivated form by a 1,5-sigmatropic shift and to a linear 6-substituted DHA. In addition, elimination of hydrogen cyanide from the photoactive DHA gave both bent and linear azulene dyes. In a nematic host that has no absorbance around 350 nm, it was found that only the linear DHA derivative has nematic properties; however, both 6- and 7-substituted DHAs were found to have large order parameters. In the nematic host, ring opening of either DHA to the corresponding vinylheptafulvene resulted in a decrease in dichroic order parameter and an unusually fast back-reaction to a mixture of both DHAs. Likewise, only the linear azulene derivative showed mesomorphic properties. In the same nematic host, large order parameters were also observed for these dyes.

AB - Photoswitches and dyes in the liquid-crystalline nematic phase have the potential for use in a wide range of applications. A large order parameter is desirable to maximize the change in properties induced by an external stimulus. A set of photochromic and nonphotochromic dyes were investigated for these applications. It was found that a bent-shaped 7-substituted dihydroazulene (DHA) photoswitch exhibited liquid-crystalline properties. Further investigation demonstrated that this material actually followed two distinct reaction pathways on heating, to a deactivated form by a 1,5-sigmatropic shift and to a linear 6-substituted DHA. In addition, elimination of hydrogen cyanide from the photoactive DHA gave both bent and linear azulene dyes. In a nematic host that has no absorbance around 350 nm, it was found that only the linear DHA derivative has nematic properties; however, both 6- and 7-substituted DHAs were found to have large order parameters. In the nematic host, ring opening of either DHA to the corresponding vinylheptafulvene resulted in a decrease in dichroic order parameter and an unusually fast back-reaction to a mixture of both DHAs. Likewise, only the linear azulene derivative showed mesomorphic properties. In the same nematic host, large order parameters were also observed for these dyes.

KW - Journal Article

U2 - 10.1002/chem.201700055

DO - 10.1002/chem.201700055

M3 - Article

C2 - 28195368

VL - 23

SP - 5090

EP - 5103

JO - Chemistry : A European Journal

JF - Chemistry : A European Journal

SN - 0947-6539

IS - 21

ER -