Abstract
The advantages and disadvantages of the various methods used to study semiconducting discotic liquid crystals are surveyed. Comprehensive tables are provided of the charge-carrier mobilities of discotic liquid crystals. Interpretations of these mobilities are discussed as well as some of the remaining, outstanding problems.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Shen, X., et al.: Orientational ordering and dynamics in the columnar phase of a discotic liquid crystal studied by deuteron NMR spectroscopy. J. Chem. Phys. 108(10), 4324–4332 (1998). doi:10.1063/1.475833
Dvinskikh, S.V., et al.: Molecular self-diffusion in a columnar liquid crystalline phase determined by deuterium NMR. Phys. Rev. E Stat. Nonlinear Soft Matter Phys. 65(5 Pt 1), 050702/1–050702/4 (2002). doi:10.1103/PhysRevE.65.050702
Van Keulen, J., et al.: Electrical conductivity in hexaalkoxytriphenylenes. Recueil des Travaux Chimiques des Pays-Bas. 106(10), 534–536 (1987). doi:10.1002/recl.19871061004
Boden, N., et al.: One-dimensional electronic conductivity in discotic liquid crystals. Chem. Phys. Lett. 152(1), 94–99 (1988). doi:10.1016/0009-2614(88)87334-2
Arikainen, E.O., et al.: Effects of side-chain length on the charge transport properties of discotic liquid crystals and their implications for the transport mechanism. J. Mater. Chem. 5(12), 2161–2165 (1995). doi:10.1039/JM9950502161
Bushby, R.J.: Unpublished
Arikainen, E.O.: Spectroscopic Studies of the nature of charge carriers in one-dimensional electronically conducting discotic liquid crystals, p. 192. School of Chemistry, University of Leeds (1996)
Boden, N., et al.: First observation of a n-doped quasi-One-dimensional electronically-conducting discotic liquid crystal. J. Am. Chem. Soc. 116(23), 10807–10808 (1994). doi:10.1021/ja00102a065
Boden, N., Bushby, R.J., Clements, J.: Mechanism of quasi-one-dimensional electronic conductivity in discotic liquid crystals. J. Chem. Phys. 98(7), 5920–5231 (1993). doi:10.1063/1.464886
Boden, N., et al.: Characterization of the cationic species formed in p-doped discotic liquid crystals. J. Mater. Chem. 5(10), 1741–1748 (1995). doi:10.1039/JM9950501741
Borner, R.C.: Electronically conducting discotic liquid crystals, p. 168. School of Chemistry, University of Leeds (1992)
Schouten, P.G., et al.: Radiation-induced conductivity in polymerized and nonpolymerized columnar aggregates of phthalocyanine. J. Am. Chem. Soc. 114(23), 9028–9034 (1992). doi:10.1021/ja00049a039
Warman, J.M., Van De Craats, A.M.: Charge mobility in discotic materials studied by PR-TRMC. Mol. Cryst. Liq. Cryst. 396, 41–72 (2003). doi:10.1080/15421400390213186
Van de Craats, A.M., et al.: Mechanism of charge transport along columnar stacks of a triphenylene dimer. J. Phys. Chem. B 102(48), 9625–9634 (1998). doi:10.1021/jp9828989
Piris, J., et al.: Aligned thin films of discotic hexabenzocoronenes: anisotropy in the optical and charge transport properties. Adv. Funct. Mater. 14(11), 1053–1061 (2004). doi:10.1002/adfm.200400182
Piris, J., Pisula, W., Warman, J.M.: Anisotropy of the optical absorption and photoconductivity of a zone-cast film of a discotic hexabenzocoronene. Synth. Met. 147(1–3), 85–89 (2004). doi:10.1016/j.synthmet.2004.06.032
Saeki, A., et al.: Charge-carrier dynamics in polythiophene films studied by in-situ measurement of flash-photolysis time-resolved microwave conductivity (FP-TRMC) and transient optical spectroscopy (TOS). Philos. Mag. 86(9), 1261–1276 (2006). doi:10.1080/14786430500380159
Sakurai, T., et al.: Prominent electron transport property observed for triply fused metalloporphyrin dimer: directed columnar liquid crystalline assembly by amphiphilic molecular design. J. Am. Chem. Soc. 130(42), 13812–13813 (2008). doi:10.1021/ja8030714
Adam, D., et al.: Transient photoconductivity in a discotic liquid crystal. Phys. Rev. Lett. 70(4), 457–460 (1993). doi:10.1103/PhysRevLett.70.457
Adam, D., et al.: Fast photoconduction in the highly ordered columnar phase of a discotic liquid crystal. Nature 371(6493), 141–143 (1994). doi:10.1038/371141a0
Kepler, R.G.: Charge carrier production and mobility in anthracene crystals. Phys. Rev. 119, 1226–1229 (1960). doi:10.1103/PhysRev.119.1226
Muller-Horsche, E., Haarer, D., Scher, H.: Transition from dispersive to nondispersive transport: photoconduction of polyvinylcarbarzole. Condens. Matter Mater. Phys. 35(3), 1273–1280 (1987). doi:10.1103/PhysRevB.35.1273
Christ, T., Stuempflen, V., Wendorff, J.H.: Light-emitting diodes based on a discotic main chain polymer. Macromol. Rapid Commun. 18(2), 93–98 (1997). doi:10.1002/marc.1997.030180204
Mott, N.F., Gurney, D.: Electronic Processes in Ionic Crystals. Academic Press, New York (1970)
Bushby, R.J., et al.: Enhanced charge conduction in discotic liquid crystals. J. Mater. Chem. 11, 1982–1984 (2001). doi:10.1039/b104112f
McNeill, A., et al.: Discotic liquid crystals. In: 3D Nanoelectronic Computer Architecture and Implementation. Taylor & Francis, Philadelphia (2004)
Garcia-Frutos, E.M., et al.: High charge mobility in discotic liquid-crystalline triindoles: just a core business? Angew. Chem. 50, 7399–7402 (2011). doi:10.1002/anie.201005820
Bjornholm, T., Hassenkam, T., Reitzel, N.: Supramolecular organization of highly conducting organic thin films by the Langmuir-Blodgett technique. J. Mater. Chem. 9(9), 1975–1990 (1999). doi:10.1039/A903019K
Pisula, W., et al.: A zone-casting technique for device fabrication of field-effect transistors based on discotic hexa-peri-hexabenzocoronene. Adv. Mater. 17(6), 684–689 (2005). doi:10.1002/adma.200401171
Pisula, W., et al.: Exceptionally long-range self-assembly of hexa-peri-hexabenzocoronene with dove-tailed alkyl substituents. J. Am. Chem. Soc. 126(26), 8074–8075 (2004). doi:10.1021/ja048351r
Gearba, R.I., et al.: Homeotropic alignment of columnar liquid crystals in open films by means of surface nanopatterning. Adv. Mater. 19(6), 815–820 (2007). doi:10.1002/adma.200602460
Shklyarevskiy, I.O., et al.: High anisotropy of the field-effect transistor mobility in magnetically aligned discotic liquid-crystalline semiconductors. J. Am. Chem. Soc. 127(46), 16233–16237 (2005). doi:10.1021/ja054694t
Bramble, J.P., et al.: Planar alignment of columnar discotic liquid crystals by isotropic phase dewetting on chemically patterned surfaces. Adv. Funct. Mater. 20(6), 914–920 (2010). doi:10.1002/adfm.200902140
de Leeuw, D.M., et al.: Stability of n-type doped conducting polymers and consequences for polymeric microelectronic devices. Synth. Met. 87(1), 53–59 (1997). doi:10.1016/S0379-6779(97)80097-5
Iino, H., et al.: Fast ambipolar carrier transport and easy homeotropic alignment in a metal-free phthalocyanine derivative. Jpn. J. Appl. Phys. Part 2 Lett. Express Lett. 44(42–45), L1310–L1312 (2005). doi:10.1143/JJAP.44.L1310
Iino, H., et al.: High electron mobility of 0.1 cm2 V−1 s−1 in the highly ordered columnar phase of hexahexylthiotriphenylene. Appl. Phys. Lett. 87(19), 192105/1–192105/3 (2005). doi:10.1063/1.2128066
Iino, H., et al.: Fast electron transport in discotic columnar phases of triphenylene derivatives. Jpn. J. Appl. Phys. Part 1 Regul. Pap. Br. Commun. Rev. Pap. 45(1B), 430–433 (2006). doi:10.1143/JJAP.45.430
Boden, N., et al.: Enhanced conduction in the discotic mesophase. Mol. Cryst. Liq. Cryst. 410, 541–549 (2004). doi:10.1080/15421400490434324
Simmerer, J., et al.: Transient photoconductivity in a discotic hexagonal plastic crystal. Adv. Mater. 8(10), 815–819 (1996). doi:10.1002/adma.19960081010
Hirai, Y., et al.: Enhanced hole-transporting behavior of discotic liquid-crystalline physical gels. Adv. Funct. Mater. 18(11), 1668–1675 (2008). doi:10.1002/adfm.200701313
Wegewijs, B.R., et al.: Charge-carrier mobilities in binary mixtures of discotic triphenylene derivatives as a function of temperature. Phys. Rev. B Condens. Matter Mater. Phys. 65(24), 245112/1–245112/8 (2002). doi:10.1103/PhysRevB.65.245112
Nakayama, H., et al.: Measurements of carrier mobility and quantum yield of carrier generation in discotic liquid crystal hexahexyl-oxytriphenylene by time-of-flight method. Jpn. J. Appl. Phys. Part 2 Lett. 38(9A/B), L1038–L1041 (1999). doi:10.1143/JJAP.38.L1038
Mizoshita, N., et al.: The positive effect on hole transport behaviour in anisotropic gels consisting of discotic liquid crystals and hydrogen-bonded fibres. Chem. Commun. 5, 428–429 (2002). doi:10.1039/B111380C
Miyake, Y., et al.: Carrier mobility of a columnar mesophase formed by a perfluoroalkylated triphenylene. Synth. Met. 159(9–10), 875–879 (2009). doi:10.1016/j.synthmet.2009.01.044
Van de Craats, A.M., et al.: The mobility of charge carriers in all four phases of the columnar discotic material hexakis(hexylthio)triphenylene. Combined TOF and PR-TRMC results. Adv. Mater. 8(10), 823–826 (1996). doi:10.1002/adma.19960081012
Iino, H., et al.: Hopping conduction in the columnar liquid crystal phase of a dipolar discogen. J. Appl. Phys. 100(4), 043716/1–043716/4 (2006). doi:10.1063/1.2219692
Bushby, R.J., et al.: Molecular engineering of triphenylene-based discotic liquid crystal conductors. Optoelectron. Rev. 13(4), 269–279 (2005)
Tate, D.J.: Applications of discotic liquid crystals in organic electronics, p. 237. School of Chemistry, University of Leeds (2008)
Ochse, A., et al.: Transient photoconduction in discotic liquid crystals. Phys. Chem. Chem. Phys. 1(8), 1757–1760 (1999). doi:10.1039/A808615J
Bleyl, I., et al.: Photopolymerization and transport properties of liquid crystalline triphenylenes. Mol. Cryst. Liq. Cryst. Sci. Technol. Section A Mol. Cryst. Liq. Cryst. 299, 149–155 (1997). doi:10.1080/10587259708041987
Bleyl, I., et al.: One-dimensional hopping transport in a columnar discotic liquid-crystalline glass. Philos. Mag. B Phys. Condens. Matter Stat. Mech. Electron. Opt. Magn. Prop. 79(3), 463–475 (1999). doi:10.1080/014186399257258
Paraschiv, I., et al.: H-bond-stabilized triphenylene-based columnar discotic liquid crystals. Chem. Mater. 18(4), 968–974 (2006). doi:10.1021/cm052221f
Paraschiv, I., et al.: Hydrogen-bond stabilized columnar discotic benzenetrisamides with pendant triphenylene groups. J. Mater. Chem. 18(45), 5475–5481 (2008). doi:10.1039/B805283B
Gearba, R.I., et al.: Tailoring discotic mesophases: columnar order enforced with hydrogen bonds. Adv. Mater. 15(19), 1614–1618 (2003). doi:10.1002/adma.200305137
Kreouzis, T., et al.: Enhanced electronic transport properties in complementary binary discotic liquid crystal systems. Chem. Phys. 262(2–3), 489–497 (2000). doi:10.1016/S0301-0104(00)00323-2
Donovan, K.J., et al.: Molecular engineering the phototransport properties of discotic liquid crystals. Mol. Cryst. Liq. Cryst. 396, 91–112 (2003). doi:10.1080/15421400390213221
Tate, D.J., et al.: Improved syntheses of high hole mobility phthalocyanines: a case of steric assistance in the cyclo-oligomerisation of phthalonitriles. Beilstein J. Org. Chem. 8(14), 120–128 (2012). doi:10.3762/bjoc.8.14
Schouten, P.G., et al.: The effect of structural modifications on charge migration in mesomorphic phthalocyanines. J. Am. Chem. Soc. 116(15), 6880–6894 (1994). doi:10.1021/ja00094a048
van de Craats, A.M., Warman, J.M.: The influence of chain-to-core coupling on the charge transport and mesomorphic properties of discotic materials. Synth. Met. 121(1–3), 1287–1288 (2001). doi:10.1016/S0379-6779(00)01219-4
van de Craats, A.M.: Charge transport in self-aggregating columnar systems such as phthalocyanines, triphenylenes and benzocoronenes. The formation, migration and recombination of charge carriers in various phases of the materials studied is investigated by making use of the time-resolved microwave conductivity technique, PR-TRMC. Opto-electronic Materials, Delft University of Technology (2000)
Ban, K., et al.: Discotic liquid crystals of transition metal complexes. 29. Mesomorphism and charge transport properties of alkylthio-substituted phthalocyanine rare-earth metal sandwich complexes. J. Mater. Chem. 11(2), 321–331 (2001). doi:10.1039/B003984P
Fujikake, H., et al.: Time-of-flight analysis of charge mobility in a Cu-phthalocyanine-based discotic liquid crystal semiconductor. Appl. Phys. Lett. 85(16), 3474–3476 (2004). doi:10.1063/1.1805178
Mori, T., Takeuchi, H., Fujikawa, H.: Field-effect transistors based on a polycyclic aromatic hydrocarbon core as a two-dimensional conductor. J. Appl. Phys. 97(6), 066102/1–066102/3 (2005). doi:10.1063/1.1862757
Fechtenkotter, A., et al.: Discotic liquid crystalline hexabenzocoronenes carrying chiral and racemic branched alkyl chains: supramolecular engineering and improved synthetic methods. Tetrahedron 57(17), 3769–3783 (2001). doi:10.1016/S0040-4020(01)00252-6
Ito, S., et al.: Synthesis and self-assembly of functionalized hexa-peri-hexabenzocoronenes. Chem. A Eur. J. 6(23), 4327–4342 (2000). doi:10.1002/1521-3765(20001201)6:23<4327::AID-CHEM4327>3.0.CO;2-7
Van De Craats, A.M., et al.: Record charge carrier mobility in a room temperature discotic liquid-crystalline derivative of hexabenzocoronene. Adv. Mater. 11(17), 1469–1472 (1999). doi:10.1002/(SICI)1521-4095(199912)11:17<1469::AID-ADMA1469>3.0.CO;2-K
Pisula, W., et al.: Relation between supramolecular order and charge carrier mobility of branched alkyl hexa-peri-hexabenzocoronenes. Chem. Mater. 18(16), 3634–3640 (2006). doi:10.1021/cm0602343
van de Craats, A.M., et al.: Meso-epitaxial solution growth of self-organizing discotic liquid crystalline semiconductors. Adv. Funct. Mater. 15(6), 495–499 (2003). doi:10.1002/adma.200390114
Kastler, M., et al.: Room-temperature nondispersive hole transport in a discotic liquid crystal. Appl. Phys. Lett. 89(25), 252103/1–252103/3 (2006). doi:10.1063/1.2408654
Watson, M.D., et al.: Peralkylated coronenes via regiospecific hydrogenation of hexa-peri-hexabenzocoronenes. J. Am. Chem. Soc. 126(3), 766–771 (2004). doi:10.1021/ja037522+
Iyer, V.S., et al.: A soluble C60 graphite segment. Angew. Chem. Int. Ed. 37(19), 2696–2699 (1998). doi:10.1002/(SICI)1521-3773(19981016)37:19<2696::AID-ANIE2696>3.0.CO;2-E
Debije, M.G., et al.: The optical and charge transport properties of discotic materials with large aromatic hydrocarbon cores. J. Am. Chem. Soc. 126(14), 4641–4645 (2004). doi:10.1021/ja0395994
Tomovic, Z., Watson, M.D., Muellen, K.: Superphenalene-based columnar liquid crystals. Angew. Chem. Int. Ed. 43(6), 755–758 (2004). doi:10.1002/anie.200352855
Zhang, Y.-D., et al.: Columnar discotic liquid-crystalline oxadiazoles as electron-transport materials. Langmuir 19(16), 6534–6536 (2003). doi:10.1021/la0341456
Boden, N., et al.: 2,3,7,8,12,13-Hexakis[2-(2-methoxyethoxy)ethoxy]tricycloquinazoline: a discogen which allows enhanced levels of n-doping. Liq. Cryst. 28(12), 1739–1748 (2001). doi:10.1080/02678290110082383
Sienkowska, M.J., et al.: Photoconductivity of liquid crystalline derivatives of pyrene and carbazole. J. Mater. Chem. 17(14), 1392–1398 (2007). doi:10.1039/B612253A
Van de Craats, A.M., et al.: Charge transport in mesomorphic derivatives of perylene. Synth. Met. 102(1–3), 1550–1551 (1999). doi:10.1016/S0379-6779(98)00554-2
Struijk, C.W., et al.: Liquid crystalline perylene diimides: architecture and charge carrier mobilities. J. Am. Chem. Soc. 122(45), 11057–11066 (2000). doi:10.1021/ja000991g
Tsao, H.N., et al.: From ambi- to unipolar behavior in discotic dye field-effect transistors. Adv. Mater. 20(14), 2715–2719 (2008). doi:10.1002/adma.200702992
Monobe, H., Mima, S., Shimizu, Y.: Carrier mobility of discotic lamellar mesophases of 5,10,15,20-tetrakis(4-n-pentadecylphenyl)porphyrin. Chem. Lett. 9, 1004–1005 (2000)
Yuan, Y., Gregg, B.A., Lawrence, M.F.: Time-of-flight study of electrical charge mobilities in liquid-crystalline zinc octakis(beta -octoxyethyl) porphyrin films. J. Mater. Res. 15(11), 2494–2498 (2000). doi:10.1557/JMR.2000.0358
Schouten, P.G., et al.: Charge migration in supramolecular stacks of peripherally substituted porphyrins. Nature 353(6346), 736–737 (1991). doi:10.1038/353736a0
Destrade, C., et al.: Disk-like mesogen polymorphism. Mol. Cryst. Liq. Cryst. 106(1–2), 121–146 (1984). doi:10.1080/00268948408080183
Chiang, L.Y., et al.: Highly oriented fibers of discotic liquid crystal. J. Chem. Soc. Chem. Commun. 11, 695–696 (1985). doi:10.1039/C39850000695
Safinya, C.R., et al.: Synchrotron x-ray scattering study of freely suspended discotic strands. Mol. Cryst. Liq. Cryst. 123(1–4), 205–216 (1985). doi:10.1080/00268948508074778
Arikainen, E.O., et al.: Complimentary polytopic interactions. Angew. Chem. Int. Ed. 39(13), 2333–2336 (2000). doi:10.1002/1521-3757(20000703)112:13<2423::AID-ANGE2423>3.0.CO;2-R
Bushby, R.J., et al.: The stability of columns comprising alternating triphenylene and hexaphenyltriphenylene molecules: variations in the structure of the hexaphenyltriphenylene component. Liq. Cryst. 33(6), 653–664 (2006). doi:10.1080/02678290600682078
Borsenberger, P.M., O’Regan, M.B.: The role of dipole moments on hole transport in triphenylamine doped poly(styrene). Chem. Phys. 200(1,2), 257–263 (1995). doi:10.1016/0301-0104(95)00195-T
Lemaur, V., et al.: Charge transport properties in discotic liquid crystals: a quantum-chemical insight into structure-property relationships. J. Am. Chem. Soc. 126, 3271–3279 (2004). doi:10.1021/ja0390956. Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved
van de Craats, A.M., Warman, J.M.: The core-size effect on the mobility of charge in discotic liquid crystalline materials. Adv. Mater. 13(2), 130–133 (2001). doi:10.1002/1521-4095(200101)13:2<130::AID-ADMA130>3.0.CO;2-L
Meot-Ner, M.: Dimer cations of polycyclic aromatics. Experimental bonding energies and resonance stabilization. J. Phys. Chem. 84(21), 2724–2728 (1980)
Mautner, M.: Structurally complex organic ions: thermochemistry and noncovalent interactions. Acc. Chem. Res. 17(5), 186–193 (1984). doi:10.1021/ar00101a006
Terahara, A., et al.: Transannular interactions in dimer cation radicals of naphthalene derivatives. Conformation anomaly and stabilization energy. J. Phys. Chem. 90(8), 1564–1571 (1986). doi:10.1021/j100399a022
Ohya-Nishiguchi, H., Ide, H., Hirota, N.: Spin densities in the trimer cation radical of coronene. Chem. Phys. Lett. 66(3), 581–583 (1979). doi:10.1016/0009-2614(79)80344-9
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Bushby, R.J., Tate, D.J. (2013). Columnar Liquid Crystalline Semiconductors. In: Bushby, R., Kelly, S., O'Neill, M. (eds) Liquid Crystalline Semiconductors. Springer Series in Materials Science, vol 169. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-2873-0_3
Download citation
DOI: https://doi.org/10.1007/978-90-481-2873-0_3
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-2872-3
Online ISBN: 978-90-481-2873-0
eBook Packages: Physics and AstronomyPhysics and Astronomy (R0)