Room-temperature discotic liquid-crystalline coronene diimides exhibiting high charge-carrier mobility in air

Six N,N′,5,11-tetrasubstituted coronene-2,3,8,9-tetracarboxydiimides have been synthesised incorporating 3,4,5-tri(n-dodecyloxy)phenyl or 2-(n-decyl)-n-tetradecyl groups in various positions. Differential scanning calorimetry, polarised optical microscopy, and X-ray diffraction indicate that all form columnar discotic mesophases from around room temperature to around 200 °C. Charge-carrier mobility values, which energetic considerations suggest are electron mobility values, have been determined in non-aligned samples cooled from the isotropic melt using the space-charge-limited current technique. The highest mobility, 6.7 cm2V−1 s−1, was found in N,N′-bis(n-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecylfluorooctyl)-5,11-bis(3-[{3,4,5-tri(n-dodecyloxy)phenyl}carbonyloxy]-n-propyl)coronene-2,3,8,9-tetracarboxydiimide, which X-ray diffraction suggests is the most highly ordered of the materials examined.

[1]  Heinz Bässler,et al.  Charge transport in disordered molecular solids , 1991 .

[2]  Jun-ichi Hanna,et al.  Very high time-of-flight mobility in the columnar phases of a discotic liquid crystal , 2005 .

[3]  K. Ohta,et al.  Self-organization and photoreactivity of anthryl dendron having perfluoroalkyl chains at the terminals , 2006 .

[4]  Alessandro Curioni,et al.  N-type organic thin-film transistor with high field-effect mobility based on a N,N′-dialkyl-3,4,9,10-perylene tetracarboxylic diimide derivative , 2002 .

[5]  Myongsoo Lee,et al.  Synthesis and Mesomorphic Properties of Palladium(II) Complexes Based on 3,4,5-Trialkoxy Benzonitrile Ligands , 1997 .

[6]  D. M. Leeuw,et al.  Thickness scaling of the space-charge-limited current in poly(p-phenylene vinylene) , 2005 .

[7]  D. Haarer,et al.  High electron mobility of 0.1cm2V−1s−1 in the highly ordered columnar phase of hexahexylthiotriphenylene , 2005 .

[8]  Jean-Luc Brédas,et al.  Organic Thin Film Transistors Based on N-Alkyl Perylene Diimides: Charge Transport Kinetics as a Function of Gate Voltage and Temperature , 2004 .

[9]  S. Barlow,et al.  A fluorine-substituted hexakisdecyloxy- hexa-peri-hexabenzocoronene. , 2005, Organic letters.

[10]  V. Percec,et al.  Spherical Supramolecular Minidendrimers Self-Organized in an “Inverse Micellar”-like Thermotropic Body-Centered Cubic Liquid Crystalline Phase , 2000 .

[11]  High charge-carrier mobility in an amorphous hexaazatrinaphthylene derivative. , 2005, Journal of the American Chemical Society.

[12]  P. Murgatroyd,et al.  Theory of space-charge-limited current enhanced by Frenkel effect , 1970 .

[13]  Liquid Crystalline Coronene Derivatives with Extraordinary Fluorescence Properties. , 1998, Angewandte Chemie.

[14]  G. Jabbour,et al.  Synthesis of novel pyrene discotics for potential electronic applications , 2007 .

[15]  F. Würthner,et al.  Synthesis and optical and electrochemical properties of core-fluorinated perylene bisimides. , 2006, Organic letters.

[16]  Kenneth D. Singer,et al.  Correlated polaron transport in a quasi-one-dimensional liquid crystal , 2006 .

[17]  G. Wegner,et al.  Organization of Charge‐Carrier Pathways for Organic Electronics , 2006 .

[18]  J. Warman,et al.  The Core‐Size Effect on the Mobility of Charge in Discotic Liquid Crystalline Materials , 2001 .

[19]  Zhenan Bao,et al.  Core‐Fluorinated Perylene Bisimide Dyes: Air Stable n‐Channel Organic Semiconductors for Thin Film Transistors with Exceptionally High On‐to‐Off Current Ratios , 2007 .

[20]  Tobin J Marks,et al.  Tuning orbital energetics in arylene diimide semiconductors. materials design for ambient stability of n-type charge transport. , 2007, Journal of the American Chemical Society.

[21]  E. Sudhölter,et al.  Liquid Crystalline Perylene diimides : Architecture and Charge Carrier Mobilities , 2000 .

[22]  M. McGehee,et al.  Organic bulk heterojunction solar cells using poly(2,5-bis(3-tetradecyllthiophen-2-yl)thieno[3,2,-b]thiophene) , 2008 .

[23]  Howard E. Katz,et al.  Naphthalenetetracarboxylic Diimide-Based n-Channel Transistor Semiconductors: Structural Variation and Thiol-Enhanced Gold Contacts , 2000 .

[24]  Chung‐Chih Wu,et al.  Functionalized dibenzo[g,p]chrysenes: variable photophysical and electronic properties and liquid-crystal chemistry. , 2008, Organic letters.

[25]  P. Schuhmacher,et al.  Fast photoconduction in the highly ordered columnar phase of a discotic liquid crystal , 1994, Nature.

[26]  Yongfang Li,et al.  Effect of branched conjugation structure on the optical, electrochemical, hole mobility, and photovoltaic properties of polythiophenes. , 2006, The journal of physical chemistry. B.

[27]  Zhijian Chen,et al.  Preparation and characterization of regioisomerically pure 1,7-disubstituted perylene bisimide dyes. , 2004, The Journal of organic chemistry.

[28]  S. So,et al.  Determination of carrier mobility in phenylamine by time-of-flight, dark-injection, and thin film transistor techniques , 2008 .

[29]  M. Kempe,et al.  Columnar Discotic Liquid-Crystalline Oxadiazoles as Electron-Transport Materials , 2003 .

[30]  John M. Warman,et al.  Record Charge Carrier Mobility in a Room‐Temperature Discotic Liquid‐Crystalline Derivative of Hexabenzocoronene , 1999 .

[31]  Zhenan Bao,et al.  Air Stable n-Channel Organic Semiconductors for Thin Film Transistors Based on Fluorinated Derivatives of Perylene Diimides , 2007 .

[32]  H. Bock,et al.  Liquid-crystalline and electron-deficient coronene oligocarboxylic esters and imides by twofold benzogenic Diels-Alder reactions on perylenes. , 2007, Chemistry.

[33]  Junsheng Yu,et al.  High Electron Mobility in Room‐Temperature Discotic Liquid‐Crystalline Perylene Diimides , 2005 .

[34]  S. Diele,et al.  Fluorescent J-type aggregates and thermotropic columnar mesophases of perylene bisimide dyes. , 2001, Chemistry.

[35]  E. W. Meijer,et al.  Synthesis of n-type perylene bisimide derivatives and their orthogonal self-assembly with p-type oligo(p-phenylene vinylene)s. , 2004, Journal of the American Chemical Society.

[36]  Khizar-ul-Haq,et al.  The estimation of electron mobility of 4,7-diphyenyl-1, 10-phenanthroline using space-charge-limited currents , 2008 .

[37]  George G. Malliaras,et al.  Temperature- and field-dependent electron and hole mobilities in polymer light-emitting diodes , 1999 .

[38]  K. Kiyohara,et al.  Mesomorphic properties of symmetrical and asymmetrical triphenylene homologues possessing fluoroalkylated side chains , 2007 .

[39]  Eung-Gun Kim,et al.  Molecular n‐Type Doping of 1,4,5,8‐Naphthalene Tetracarboxylic Dianhydride by Pyronin B Studied Using Direct and Inverse Photoelectron Spectroscopies , 2006 .

[40]  G. Ortaggi,et al.  New hydrosoluble perylene and coronene derivatives , 2004 .

[41]  Christopher D. Simpson,et al.  Epitaxial composite layers of electron donors and acceptors from very large polycyclic aromatic hydrocarbons. , 2002, Journal of the American Chemical Society.

[42]  Zhaohui Wang,et al.  Air-stable n-type semiconductor: core-perfluoroalkylated perylene bisimides. , 2008, Organic letters.

[43]  T. M. Klapwijk,et al.  Space charge limited transport and time of flight measurements in tetracene single crystals: a comparative study. , 2003, cond-mat/0308391.

[44]  R. Friend,et al.  Organic Thin Film Photovoltaic Devices from Discotic Materials , 2003 .

[45]  V. Percec,et al.  Tubular Architectures from Polymers with Tapered Side Groups. Assembly of Side Groups via a Rigid Helical Chain Conformation and Flexible Helical Chain Conformation Induced via Assembly of Side Groups , 1996 .

[46]  Klaus Müllen,et al.  Novel core-expanded rylenebis(dicarboximide) dyes bearing pentacene units: facile synthesis and photophysical properties. , 2007, Chemistry.

[47]  S. Barlow,et al.  High electron mobility in nickel bis(dithiolene) complexes , 2007 .

[48]  Bernard Kippelen,et al.  A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells. , 2007, Journal of the American Chemical Society.

[49]  R. Friend,et al.  Self-organized discotic liquid crystals for high-efficiency organic photovoltaics. , 2001, Science.

[50]  H. Bock,et al.  An all-columnar bilayer light-emitting diode , 2000 .

[51]  Tobin J Marks,et al.  High-mobility air-stable n-type semiconductors with processing versatility: dicyanoperylene-3,4:9,10-bis(dicarboximides). , 2004, Angewandte Chemie.

[52]  E. Sudhölter,et al.  Hydrogen-bond stabilized columnar discotic benzenetrisamides with pendant triphenylene groups , 2008 .

[53]  Y. Tohda,et al.  A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines , 1975 .

[54]  Tung Huei Ke,et al.  Balanced ambipolar charge carrier mobility in mixed layers for application in hybrid white organic light-emitting diodes , 2008 .

[55]  H. Spiess,et al.  Highly Ordered Columnar Structures from Hexa-peri-hexabenzocoronenes-Synthesis, X-ray Diffraction, and Solid-State Heteronuclear Multiple-Quantum NMR Investigations. , 1999, Angewandte Chemie.

[56]  P. Heremans,et al.  Current–voltage characteristics of a tetracene crystal:Space charge or injection limited conductivity? , 2004 .

[57]  Zhenan Bao,et al.  Air-stable n-channel organic thin-film transistors with high field-effect mobility based on N,N′-bis(heptafluorobutyl)-3,4:9,10-perylene diimide , 2007 .

[58]  Zhijian Chen,et al.  Tetrachloro-substituted perylene bisimide dyes as promising n-type organic semiconductors: studies on structural, electrochemical and charge transport properties. , 2004, Chemphyschem : a European journal of chemical physics and physical chemistry.

[59]  Y. Nagao,et al.  Design of Near-Infrared Dyes Based on π-Conjugation System Extension 2. Theoretical Elucidation of Framework Extended Derivatives of Perylene Chromophore , 2001 .

[60]  Eva M. García-Frutos,et al.  New Electrode-Friendly Triindole Columnar phases with High Hole Mobility , 2008 .

[61]  G. Ortaggi,et al.  Specific interactions with intra- and intermolecular G-quadruplex DNA structures by hydrosoluble coronene derivatives: a new class of telomerase inhibitors. , 2007, Bioorganic & medicinal chemistry.

[62]  M. Debije,et al.  High charge-carrier mobility in pi-deficient discotic mesogens: design and structure-property relationship. , 2005, Chemistry.

[63]  Gilles Horowitz,et al.  Evidence for n‐type conduction in a perylene tetracarboxylic diimide derivative , 1996 .

[64]  W. R. Salaneck,et al.  Effect of interfaces on the alignment of a discotic liquid-crystalline phthalocyanine. , 2006, Langmuir : the ACS journal of surfaces and colloids.

[65]  K. Müllen,et al.  Liquid crystalline coronene derivatives , 2001 .

[66]  E. Waclawik,et al.  Current-voltage characteristics of poly(3-hexylthiophene) diodes at room temperature , 2009 .

[67]  Bumjoon J. Kim,et al.  The influence of poly(3-hexylthiophene) regioregularity on fullerene-composite solar cell performance. , 2008, Journal of the American Chemical Society.

[68]  K. Müllen,et al.  Synthesis and Self-Organization of Core-Extended Perylene Tetracarboxdiimides with Branched Alkyl Substituents , 2006 .

[69]  S. Laschat,et al.  Discotic liquid crystals: from tailor-made synthesis to plastic electronics. , 2007, Angewandte Chemie.

[70]  L. Mathias,et al.  Syntheses, Polymerization, and Characterization of Novel Semifluorinated Methacrylates, Including Novel Liquid Crystalline Materials , 1993 .

[71]  M. Kantam,et al.  Nanocrystalline copper(II) oxide catalyzed aza-Michael reaction and insertion of α-diazo compounds into N–H bonds of amines , 2009 .

[72]  K. Müllen,et al.  Facile synthetic approach to novel core-extended perylene carboximide dyes. , 2005, Chemical communications.

[73]  P. Blom,et al.  Electric-field and temperature dependence of the hole mobility in poly(p-phenylene vinylene) , 1997 .

[74]  K. Hanabusa,et al.  Enhanced Hole‐Transporting Behavior of Discotic Liquid‐Crystalline Physical Gels , 2008 .

[75]  Michael G Debije,et al.  The optical and charge transport properties of discotic materials with large aromatic hydrocarbon cores. , 2004, Journal of the American Chemical Society.

[76]  S. Barlow,et al.  A Comparative Study of Charge Mobility Measurements in a Diamine and in a Hexaazatrinaphthylene Using Different Techniques , 2008 .