Reversible photochemical control of cholesteric liquid crystals with a diamine-based diarylethene chiroptical switch

Upon addition of a chiral dopant to a nematic liquid crystal, amplification of molecular chirality can occur and consequently a cholesteric liquid crystal is formed. A major challenge in materials science consists in designing efficient chiral dopants that allow for control over chiral amplification by use of an external trigger, for example by irradiation with light, and thereby achieving the control of the dynamic and responsive structure of cholesteric liquid crystals. Here, a chiral photochromic switch bearing two chiral imine units connected viaphenyl spacers was synthesized and characterized in solution, where it can be photo-chemically converted from a colourless ring-opened form 1o to a coloured ring-closed form 1c, reversibly. We show that a small amount of 1o used as a dopant induces the formation of a stable cholesteric liquid crystal. The retention of the photochromic properties of 1, when used as a chiral dopant, allows for reversible photocontrol over the period of the cholesteric helix, and shows the highest values of helical twisting power achieved so far with diarylethene-based photoswitchable dopants.

[1]  Timothy J. Bunning,et al.  Dynamic color in stimuli-responsive cholesteric liquid crystals , 2010 .

[2]  T. White,et al.  Light-driven nanoscale chiral molecular switch: reversible dynamic full range color phototuning. , 2010, Chemical communications.

[3]  T. White,et al.  Photoinduced broadening of cholesteric liquid crystal reflectors , 2010 .

[4]  Nathalie Katsonis,et al.  Photoinduced reorganization of motor-doped chiral liquid crystals: bridging molecular isomerization and texture rotation. , 2008, Journal of the American Chemical Society.

[5]  M. Mathews,et al.  Planar chiral azobenzenophanes as chiroptic switches for photon mode reversible reflection color control in induced chiral nematic liquid crystals. , 2008, Journal of the American Chemical Society.

[6]  M. Goh,et al.  Powerful helicity inducers: axially chiral binaphthyl derivatives , 2008 .

[7]  A. Matharu,et al.  Liquid crystals for holographic optical data storage. , 2007, Chemical Society reviews.

[8]  J. W. Doane,et al.  Reversible photoswitchable axially chiral dopants with high helical twisting power. , 2007, Journal of the American Chemical Society.

[9]  H. Tian,et al.  Photochromic bisthienylethene as multi-function switches. , 2007, Chemical communications.

[10]  Nathalie Katsonis,et al.  Rotational reorganization of doped cholesteric liquid crystalline films. , 2006, Journal of the American Chemical Society.

[11]  Ben L Feringa,et al.  Amplification of chirality in liquid crystals. , 2006, Organic & biomolecular chemistry.

[12]  B. Feringa,et al.  Reversible full-range color control of a cholesteric liquid-crystalline film by using a molecular motor. , 2006, Chemistry, an Asian journal.

[13]  Nathalie Katsonis,et al.  Molecular machines: Nanomotor rotates microscale objects , 2006, Nature.

[14]  G. Mehl,et al.  Design of mesomorphic diarylethene-based photochromes. , 2004, Journal of the American Chemical Society.

[15]  He Tian,et al.  Recent progresses on diarylethene based photochromic switches. , 2004, Chemical Society reviews.

[16]  A. Pugžlys,et al.  Photochromic Properties of Perhydro- and Perfluorodithienylcyclopentene Molecular Switches , 2003 .

[17]  Richard A. van Delden,et al.  Controlling the Color of Cholesteric Liquid‐Crystalline Films by Photoirradiation of a Chiroptical Molecular Switch Used as Dopant , 2003 .

[18]  Ingo Dierking,et al.  Textures of liquid crystals , 2003 .

[19]  T. Yamaguchi,et al.  Photoswitching of Helical Twisting Power by Chiral Diarylethene Dopants , 2001 .

[20]  M. Irie,et al.  Photoinduced pitch changes in chiral nematic liquid crystals formed by doping with chiral diarylethene , 2001 .

[21]  M. Irie,et al.  An Optically Active Diarylethene Having Cholesterol Units: A Dopant for Photoswitching of Liquid Crystal Phases , 2000 .

[22]  M. Irie,et al.  Phase Transition of a Liquid Crystal Induced by Chiral Photochromic Dopants , 2000 .

[23]  Masahiro Irie,et al.  Photochromism of 1,2-Bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene in a Single-Crystalline Phase , 2000 .

[24]  Masahiro Irie,et al.  Diarylethenes for Memories and Switches. , 2000, Chemical reviews.

[25]  M. Irie,et al.  Photoswitching of Helical Twisting Power of a Chiral Diarylethene Dopant: Pitch Change in a Chiral Nematic Liquid Crystal , 2000 .

[26]  Yasushi Yokoyama,et al.  Reversible Control of the Pitch of Cholesteric Liquid Crystals by Photochromism of Chiral Fulgide Derivatives , 2000 .

[27]  B. Feringa,et al.  A new synthetic route to symmetrical photochromic diarylperfluorocyclopentenes , 1999 .

[28]  S. Kobatake,et al.  Fatigue resistant properties of photochromic dithienylethenes: by-product formation , 1999 .

[29]  Martin Brehmer,et al.  Light‐Induced Color Change of Cholesteric Copolymers , 1998 .

[30]  B. Feringa,et al.  Optically active diarylethenes for multimode photoswitching between liquid-crystalline phases , 1998 .

[31]  Y. Yokoyama,et al.  Reversible Control of Pitch of Induced Cholesteric Liquid Crystal by Optically Active Photochromic Fulgide Derivatives , 1997 .

[32]  B. Feringa,et al.  CHIROPTICAL SWITCHING BETWEEN LIQUID CRYSTALLINE PHASES , 1995 .

[33]  G. Schuster,et al.  A Liquid Crystal Opto-optical Switch: Nondestructive Information Retrieval Based on a Photochromic Fulgide as Trigger , 1995 .

[34]  S. Yarmolenko,et al.  Photosensitive chiral dopants with high twisting power , 1994 .

[35]  G. Heppke,et al.  Determination of the Cholesteric Screw Sense , 1978 .

[36]  L. Richter,et al.  Textures of liquid crystals , 1978 .