Synthesis and mesocrystalline properties of liquid crystal compounds with tetrathiafulvalene and two cyanobiphenyl units

ABSTRACT A series of ethylenedithiotetrathiafulvalene (EDT-TTF) compounds with cyanobiphenyl moieties attached with different length alkyl chains has been designed and synthesized. The phase behavior of these derivatives was investigated by a combination of polarizing optical microscopy, differential scanning calorimetry, and X-ray diffraction. Among the derivatives, the derivatives with spacer group lengths of n = 6–12 (3b–3d) show a distinct glassy transition during the heating and cooling processes, and 3c (n = 8) and 3d (n = 12) show liquid crystal (LC) phases below the isotropic temperature. An electrochemical study shows that the longer the spacer group, the more readily the target compound is oxidized. Density functional theory calculations show that the LC molecules are typical donor–σ-bridge–acceptor molecules. GRAPHICAL ABSTRACT

[1]  H. Bisoyi,et al.  Hybrid rod-like and bent-core liquid crystal dimers exhibiting biaxial smectic A and nematic phases , 2012 .

[2]  Jungeun Kim,et al.  Electric-field-responsive handle for large-area orientation of discotic liquid-crystalline molecules in millimeter-thick films. , 2011, Angewandte Chemie.

[3]  Soo‐Hyoung Lee,et al.  Liquid crystalline mesophases based on symmetric tetrathiafulvalene derivatives , 2011 .

[4]  P. Frère,et al.  Effects of aromatic spacers on the properties of organic field effect transistors based on π-extended tetrathiafulvalene derivatives , 2009 .

[5]  K. Jeong,et al.  Room-temperature columnar liquid crystal based on tetrathiafulvalene , 2008 .

[6]  D. Amabilino,et al.  TTF-based bent-core liquid crystals. , 2008, Chemical communications.

[7]  Quan Li,et al.  Liquid Crystal Trimers Composed of Banana-Shaped and Rodlike Anisometric Segments : Synthesis and Characterization , 2007 .

[8]  Wojciech Pisula,et al.  Discotic liquid crystals: a new generation of organic semiconductors. , 2007, Chemical Society reviews.

[9]  Z. Shuai,et al.  Dibenzotetrathiafulvalene Bisimides: New Building Blocks for Organic Electronic Materials** , 2007 .

[10]  D. Guldi,et al.  Electronic communication in tetrathiafulvalene (TTF)/C60 systems: toward molecular solar energy conversion materials? , 2007, Accounts of chemical research.

[11]  Daoben Zhu,et al.  Linear benzene-fused bis(tetrathiafulvalene) compounds for solution processed organic field-effect transistors , 2007 .

[12]  Jianping Ma,et al.  A novel cascade supramolecular complex with a reversible nanosized 18-component H-bonded {(C6H6)6(SbF6)12}12- cage unit templated by a chiral metal-organic complex. , 2006, Inorganic chemistry.

[13]  Jingping Zhang,et al.  Preparation and crystal structure of dual-functional precursor complex bis(acetylacetonato)nickel(II) with 4-pyridyltetrathiafulvalene. , 2006, Inorganic chemistry.

[14]  C. Rovira,et al.  Tetrathiafulvalene derivatives for organic field effect transistors , 2006 .

[15]  John W. Goodby,et al.  Supermolecular liquid crystals , 2005 .

[16]  Y. Takanishi,et al.  Organic field-effect transistors based on new TTF-based liquid crystalline materials , 2005 .

[17]  Takashi Kato.  Self-Assembly of Phase-Segregated Liquid Crystal Structures , 2002, Science.

[18]  J. Segura,et al.  New planar and soluble tris-tetrathiafulvalene derivatives with threefold-symmetry , 2000 .

[19]  J. Orduna,et al.  The first discotic liquid crystal with a tetrathiafulvalene central core , 1998 .

[20]  J. Orduna,et al.  Synthesis and liquid crystal behaviour of tetrathiafulvalenes containing cyanobiphenylyloxy groups , 1998 .

[21]  B. Movaghar,et al.  Novel synthesis of calamitic and discotic liquid crystalline derivatives of tetrathiafulvalene (TTF) , 1998 .