Long-Lived Supramolecular Helices Promoted by Fluorinated Photoswitches

He Huang, Tetiana Orlova, Benjamin Matt, Nathalie Katsonis (Corresponding Author)

Research output: Contribution to journalArticleAcademicpeer-review

6 Citations (Scopus)

Abstract

Chiral azobenzenes can be used as photoswitchable dopants to control supramolecular helices in liquid crystals. However, the lack of thermal stability of the cis-isomer precludes envisioning the generation of long-lived supramolecular helices with light. Here, this study demonstrates thermally stable and axially chiral azobenzene switches that can be used as chiral dopants to create supramolecular helices from (achiral) nematic liquid crystals. Their trans-to-cis photoisomerization leads to a variation of helical twisting power that reaches up to 60%, and the helical superstructure that is engineered with light displays a relaxation time that reaches tens of hours. These results demonstrate that combining ortho-fluorination with axial chirality in molecular photoswitches constitutes an efficient strategy to promote long-lived helical states. Further, this approach shows potential to design supramolecular machines that are controlled by light entirely.

Original languageEnglish
Article number1700387
JournalMacromolecular rapid communications
Volume39
Issue number1
DOIs
Publication statusPublished - 5 Jan 2018

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Azobenzene
Doping (additives)
Photoisomerization
Liquid Crystals
Fluorination
Nematic liquid crystals
Chirality
Isomers
Relaxation time
Liquid crystals
Thermodynamic stability
Switches
azobenzene

Keywords

  • UT-Hybrid-D
  • light
  • liquid crystals
  • molecular switches
  • chirality

Cite this

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title = "Long-Lived Supramolecular Helices Promoted by Fluorinated Photoswitches",
abstract = "Chiral azobenzenes can be used as photoswitchable dopants to control supramolecular helices in liquid crystals. However, the lack of thermal stability of the cis-isomer precludes envisioning the generation of long-lived supramolecular helices with light. Here, this study demonstrates thermally stable and axially chiral azobenzene switches that can be used as chiral dopants to create supramolecular helices from (achiral) nematic liquid crystals. Their trans-to-cis photoisomerization leads to a variation of helical twisting power that reaches up to 60{\%}, and the helical superstructure that is engineered with light displays a relaxation time that reaches tens of hours. These results demonstrate that combining ortho-fluorination with axial chirality in molecular photoswitches constitutes an efficient strategy to promote long-lived helical states. Further, this approach shows potential to design supramolecular machines that are controlled by light entirely.",
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Long-Lived Supramolecular Helices Promoted by Fluorinated Photoswitches. / Huang, He; Orlova, Tetiana; Matt, Benjamin; Katsonis, Nathalie (Corresponding Author).

In: Macromolecular rapid communications, Vol. 39, No. 1, 1700387, 05.01.2018.

Research output: Contribution to journalArticleAcademicpeer-review

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T1 - Long-Lived Supramolecular Helices Promoted by Fluorinated Photoswitches

AU - Huang, He

AU - Orlova, Tetiana

AU - Matt, Benjamin

AU - Katsonis, Nathalie

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N2 - Chiral azobenzenes can be used as photoswitchable dopants to control supramolecular helices in liquid crystals. However, the lack of thermal stability of the cis-isomer precludes envisioning the generation of long-lived supramolecular helices with light. Here, this study demonstrates thermally stable and axially chiral azobenzene switches that can be used as chiral dopants to create supramolecular helices from (achiral) nematic liquid crystals. Their trans-to-cis photoisomerization leads to a variation of helical twisting power that reaches up to 60%, and the helical superstructure that is engineered with light displays a relaxation time that reaches tens of hours. These results demonstrate that combining ortho-fluorination with axial chirality in molecular photoswitches constitutes an efficient strategy to promote long-lived helical states. Further, this approach shows potential to design supramolecular machines that are controlled by light entirely.

AB - Chiral azobenzenes can be used as photoswitchable dopants to control supramolecular helices in liquid crystals. However, the lack of thermal stability of the cis-isomer precludes envisioning the generation of long-lived supramolecular helices with light. Here, this study demonstrates thermally stable and axially chiral azobenzene switches that can be used as chiral dopants to create supramolecular helices from (achiral) nematic liquid crystals. Their trans-to-cis photoisomerization leads to a variation of helical twisting power that reaches up to 60%, and the helical superstructure that is engineered with light displays a relaxation time that reaches tens of hours. These results demonstrate that combining ortho-fluorination with axial chirality in molecular photoswitches constitutes an efficient strategy to promote long-lived helical states. Further, this approach shows potential to design supramolecular machines that are controlled by light entirely.

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