New isothiocyanato liquid crystals containing thieno[3,2-b]thiophene central core

ABSTRACT New isothiocyanato liquid crystal (LC) materials based on thieno[3,2-b]thiophene core have been synthesised and characterised. Their mesomorphic and physical properties were evaluated. The results indicate that most of the new compounds exhibit only enantiotropic smectic A phases with high clearing points, and the difluorinated compounds (A3 and A6), in particular, also display a stable nematic phase with low melting points. Compared with the corresponding biphenyl and thiophene-phenyl analogues, these thieno[3,2-b]thiophene-based compounds possess increased birefringence (the highest value found to be 0.40) and mesogenic phase intervals. These new thieno[3,2-b]thiophene-based LCs exhibit a high birefringence and a high clearing point and are of potential use as components of high birefringence mixtures. Graphical Abstract

[1]  K. Garbat,et al.  Mesomorphic, optical, dielectric, elastic and viscous properties of multi-component isothiocyanato mixtures , 2013 .

[2]  R. Dabrowski,et al.  Structural, optical and dynamical properties of a high birefringence laterally fluorinated terphenyl isothiocyanate , 2015 .

[3]  Liang-Chy Chien,et al.  High birefringence difluoroisothiocyanate biphenyl tolane liquid crystals , 2006 .

[4]  M. Vuks Determination of the Optical Anisotropy of Aromatic Molecules from the Double Refraction of Crystals , 1966 .

[5]  S. Gauza,et al.  Low viscosity, high birefringence liquid crystalline compounds and mixtures , 2007 .

[6]  P. Kula,et al.  Design of new super-high birefringent isothiocyanato bistolanes – synthesis and properties , 2017 .

[7]  Ci-Ling Pan,et al.  Electrically tunable room-temperature 2/spl pi/ liquid crystal terahertz phase shifter , 2006 .

[8]  Shin‐Tson Wu,et al.  High birefringence lateral difluoro phenyl tolane liquid crystals , 2010 .

[9]  J. Goodby,et al.  Novel, highly polarizable thiophene derivatives for use in nonlinear optical applications , 2003 .

[10]  R. Dabrowski,et al.  Electrically Tunable Liquid Crystal Filters , 2010 .

[11]  S. Bernet,et al.  Near-perfect hologram reconstruction with a spatial light modulator. , 2008, Optics express.

[12]  R. Dabrowski,et al.  A comparative study of the mesomorphic properties of fluoro-isothiocyanated and fluorinated terphenyl liquid crystals from birefringence, static dielectric permittivity, splay elastic constant and rotational viscosity measurements , 2012 .

[13]  Shiping Zhu,et al.  Novel High-Performance Liquid-Crystalline Organic Semiconductors for Thin-Film Transistors , 2009 .

[14]  G. W. Gray,et al.  Synthesis, transition temperatures and optical anisotropy of some isothiocyanato-substituted biphenyls , 1993 .

[15]  T. Swager,et al.  Nematic Liquid Crystals with Bent-Rod Shapes: Mesomorphic Thiophenes with Lateral Dipole Moments , 1999 .

[16]  R. Dabrowski,et al.  Dielectric studies of the 4-n-alkyl-4'-thiocyanatobiphenyl (nBT) homologous series (n=2-10) in the isotropic and E phases , 2001 .

[17]  R. Dabrowski,et al.  New fluorinated terphenyl isothiocyanate liquid crystals , 2008 .

[18]  S.A. Khan,et al.  Demonstration of 3-dimensional wide angle laser beam scanner using liquid crystals. , 2004, Optics express.

[19]  Hsiao‐Fan Tseng,et al.  Synthesis and characterisation of liquid crystal molecules based on thieno [3,2-b] thiophene and their application in organic field-effect transistors , 2017 .

[20]  R. Dabrowski,et al.  Synthesis and properties of new non-symmetric 2,5-bis(4-alkylphenylethynyl)thiophenes , 2014 .

[21]  R. Dabrowski,et al.  Syntheses and mesomorphic properties of laterally fluorinatedphenyl isothiocyanatotolanes and their high birefringent mixtures , 2009 .

[22]  J. Svoboda,et al.  New liquid crystal based on 2-phenylthiophene central core , 2014 .

[23]  K. Garbat,et al.  Note: tunable notch filter based on liquid crystal technology for microwave applications. , 2013, The Review of scientific instruments.

[24]  Jakub Herman,et al.  High Birefringence Liquid Crystals , 2013 .

[25]  Ning Gan,et al.  The effect of lateral fluorination on the properties of phenyl-tolane liquid crystals , 2015 .

[26]  R. Dabrowski,et al.  Physical properties of laterally fluorinated isothiocyanato phenyl‐tolane liquid crystals , 2008 .

[27]  Wenliang Wang,et al.  Lateral substituent effects on UV stability of high-birefringence liquid crystals with the diaryl-diacetylene core: DFT/TD-DFT study , 2017 .

[28]  J. Zeitler,et al.  High-birefringence nematic liquid crystal for broadband THz applications , 2016 .

[29]  R. Dąbrowski,et al.  Liquid crystal phase shifters at millimeter wave frequencies , 2012 .

[30]  Neil L. Campbell,et al.  Nematic 2,5-disubstituted thiophenes , 2002 .

[31]  Yaron Silberberg,et al.  Two-dimensional phase-only spatial light modulators for dynamic phase and amplitude pulse shaping , 2009 .

[32]  Juanli Li,et al.  The effect of locations of triple bond at terphenyl skeleton on the properties of isothiocyanate liquid crystals , 2017 .

[33]  Ran Chen,et al.  Dielectric and optical anisotropy enhanced by 1,3-dioxolane terminal substitution on tolane-liquid crystals , 2015 .

[34]  Shin-Tson Wu,et al.  Tailoring the physical properties of some high birefringence isothiocyanato-based liquid crystals , 2004 .

[35]  Ran Chen,et al.  Synthesis and physical properties of tolane liquid crystals containing 2,3-difluorophenylene and terminated by a tetrahydropyran moiety , 2016 .

[36]  P. Sampson,et al.  The synthesis and mesogenic behaviour of the first series of low molar mass thieno[3,2-b]thiophene-2-carboxylate ester-based mesogens , 2009 .

[37]  I. H. Bechtold,et al.  Synthesis and characterization of some novel tetrazole liquid crystals , 2013 .

[38]  Susumu Sato,et al.  Electrically tunable lens based on a dual-frequency nematic liquid crystal. , 2006, Applied optics.

[39]  J. Watanabe,et al.  Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties , 2014 .

[40]  Shin‐Tson Wu,et al.  Synthesis and mesomorphic properties of super high birefringence isothiocyanato bistolane liquid crystals , 2007 .

[41]  R. Dabrowski,et al.  High figure‐of‐merit nematic mixtures based on totally unsaturated isothiocyanate liquid crystals , 2006 .

[42]  S. Picken,et al.  Liquid crystalline properties of all symmetric p-phenylene and 2,5-thiophene pentamers , 2009 .

[43]  M. R. Dodge,et al.  Tunable-focus flat liquid-crystal diffractive lens. , 2010, Optics letters.