Skip to main content

Discotic Liquid Crystalline Polymers: Structure and Chemistry

  • Chapter

Abstract

Mutual share of properties by Liquid Crystals and Polymers, provide a class of anisotropic materials with mechanical and thermal stability, commonly known as Liquid Crystalline Polymers (LCPs). LCPs containing Disc-shape mesogense are Discotic liquid crystalline polymers. Based on their position and connectivity in polymer backbone they can be divided into (a) discotic main chain (b) discotic side chain (c) discotic elastomers (d) discotic dendritic (e) discotic hyperbranched and (f) discotic metallomesogenic liquid crystalline polymers. An effort can be made to set a trend in the variation of physical properties of these polymers, based on various discogens, side chains and polymer back bones, on the basis of literature available.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

References

  • Bengs H, Finkelmann H, Küpfer J, Ringsdorf H, Schuhmacher P (1993) Highly oriented discotic elastomers. Makromol Chem Rapid Commun 14:445–450

    Article  Google Scholar 

  • Bisoyi HK, Kumar S (2008) Carbon nanotubes in triphenylene and rufigallol-based room temperature monomeric and polymeric discotic liquid crystals. J Mater Chem 18:3032–3039

    Article  Google Scholar 

  • Boden N, Bushby RJ, Cammidge AN (1995) Triphenylene-based discotic-liquid-crystalline polymers: a universal, rational synthesis. J Am Chem Soc 117:924–927

    Article  Google Scholar 

  • Boden N, Bushby RJ, Lu ZB (1998) A rational synthesis of polyacrylates with discogenic side groups. Liq Cryst 25:47–58

    Article  Google Scholar 

  • Boden N, Bushby RJ, Eichhorn H, Lu Z-B, Abeysekera R, Robardes AW (1999) Discotic liquid crystalline block copolymers 2: main-chain discotic liquid crystalline diblock and triblock copolymers. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst 332:293–302

    Article  Google Scholar 

  • Boden N, Bushby RJ, Cooke G, Lozman OR, Lu Z (2001) CPI: a recipe for improving applicable properties of discotic liquid crystals. J Am Chem Soc 123:7915–7916

    Article  Google Scholar 

  • Brand JD, Kübel C, Ito S, Müllen K (2000) Functionalized hexa-peri-hexabenzocoronenes: stable supramolecular order by polymerization in the discotic mesophase. Chem Mater 12:1638–1647

    Article  Google Scholar 

  • Bryant GC, Cook MJ, Ryan TG, Thorne AJ (1995) Liquid crystalline polymeric phthalocyanines. J Chem Soc Chem Commun 4:467–468

    Article  Google Scholar 

  • Cameron JH, Facher A, Lattermann G, Diele S (1997) Poly(propyleneimine) dendromesogens with hexagonal columnar mesophase. Adv Mater 9:398–403

    Article  Google Scholar 

  • Caseri W, Sauer T, Wegner G (1988) Soluble phthalocyaninato-polysiloxanes: rigid rod polymers of high molecular weight. Makromol Chem Rapid Commun 9:651–657

    Article  Google Scholar 

  • Catry C, Van der Auweraer M, De Schryver FC, Bengs H, Häussling L, Karthaus O, Ringsdorf H (1993) Conductivity and photoconductivity of undoped and doped Langmuir-Blodgett films of a polymer with hexaalkoxytriphenylene side-groups. Makromol Chem 194:2985–2999

    Article  Google Scholar 

  • Cook MJ (1995) Liquid crystalline oligomeric and polymeric phthalocyanines. Adv Mater 7:877–880

    Article  Google Scholar 

  • Disch S, Finkelmann H, Ringsdorf H, Schuhmacher P (1995) Macroscopically ordered discotic columnar networks. Macromolecules 28:2424–2428

    Article  Google Scholar 

  • Dulog L, Gittinger A, Roth S, Wagner T (1993) Synthesis and characterization of poly[2,3,9,10,16,17,23,24-octakis(dodecyloxycarbonyl)phthalocyaninatogermoxane]. Makromol Chem 194:493–500

    Article  Google Scholar 

  • Green MM, Ringsdorf H, Wagner J, Wüstefeld R (1990) Induction and variation of chirality in discotic liquid crystalline polymers. Angewandte Chem 29:1478–1481

    Article  Google Scholar 

  • Herrmann-Schönherr O, Wendorff JH, Ringsdorf H, Tschirner P (1986) Structure of an aromatic polyamide with disc-like mesogens in the main chain. Makromol Chem Rapid Commun 7:791–796

    Article  Google Scholar 

  • Hueser B, Pakula T, Spiess HW (1989) Macroscopic ordering of liquid-crystalline polymers with discotic mesogens. Macromolecules 22:1960–1963

    Article  Google Scholar 

  • Hüser B, Spiess HW (1988) Macroscopic alignment of discotic liquid-crystalline polymers in a magnetic field. Makromol Chem Rapid Commun 9:337–343

    Article  Google Scholar 

  • Imrie CT, Inkster RT, Lu Z, Ingram MD (2004) Discotic side group liquid crystal polymer electrolytes. Mol Cryst Liq Cryst 408:33–43

    Article  Google Scholar 

  • Karthaus O, Ringsdorf H, Tsukruk VV, Wendorff JH (1992) Columnar ordering of liquid-crystalline discotics in Langmuir-Blodgett films. Langmuir 8:2279–2283

    Article  Google Scholar 

  • Kouwer PHJ, Jager WF, Mijs WJ, Picken SJ (2000) Synthesis and characterization of a novel liquid crystalline polymer showing a nematic columnar to nematic discotic phase transition. Macromolecules 33:4336–4342

    Article  Google Scholar 

  • Kouwer PHJ, Gast J, Jager WF, Mijs WJ, Picken SJ (2001a) A series of novel liquid crystalline polymers showing a nematic discotic and/or a nematic columnar phase. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst 364:225–234

    Article  Google Scholar 

  • Kouwer PHJ, Jager WF, Mijs WJ, Picken SJ (2001b) The nematic lateral phase: a novel phase in discotic supramolecular assemblies. Macromolecules 34:7582–7584

    Article  Google Scholar 

  • Kouwer PHJ, Mijs WJ, Jager WF, Picken SJ (2001c) Modeling of ND and NCol phase transitions in discotic side chain polymers by the extended McMillan theory. J Am Chem Soc 123:4645–4646

    Article  Google Scholar 

  • Kouwer PHJ, Jager WF, Mijs WJ, Picken SJ (2002a) Charge transfer complexes of discotic liquid crystals: a flexible route to a wide variety of mesophases. Macromolecules 35:4322–4329

    Article  Google Scholar 

  • Kouwer PHJ, van den Berg O, Jager WF, Mijs WJ, Picken SJ (2002b) Induced liquid crystalline diversity in molecular and polymeric charge-transfer complexes of discotic mesogens. Macromolecules 35:2576–2582

    Article  Google Scholar 

  • Kouwer PHJ, Jager WF, Mijs WJ, Picken SJ (2003) Specific interactions in discotic liquid crystals. J Mater Chem 13:458–469

    Article  Google Scholar 

  • Kouwer P, Jager W, Mijs W, Picken S (2004) Substituent effects in discotic liquid crystals. Mol Cryst Liq Cryst 411:305–312

    Article  Google Scholar 

  • Kreuder W, Ringsdorf H (1983) Liquid crystalline polymers with disc-like mesogens. Makromol Chem Rapid Commun 4:807–815

    Article  Google Scholar 

  • Kreuder W, Ringsdorf H, Tschirner P (1985) Liquid crystalline polymers with disc-like mesogens in the main chain. Makromol Chem Rapid Commun 6:367–373

    Article  Google Scholar 

  • Lange U, Roznyatovskaya NV, Mirsky VM (2008) Conducting polymers in chemical sensors and arrays. Anal Chim Acta 614:1–26

    Article  Google Scholar 

  • Malthete J, Collet A (1987) Inversion of the cyclotribenzylene cone in a columnar mesophase: a potential way to ferroelectric materials. J Am Chem Soc 109:7544–7545

    Article  Google Scholar 

  • Malthete J, Collet A, Levelut A-M (1989) Mesogens containing the DOBOB group. Liq Cryst 5:123–131

    Article  Google Scholar 

  • Marcos M, Giménez R, Serrano JL, Donnio B, Heinrich B, Guillon D (2001) Dendromesogens: liquid crystal organizations of poly(amidoamine) dendrimers versus starburst structures. Chem A Eur J 7:1006–1013

    Article  Google Scholar 

  • McKenna MD, Barberá J, Marcos M, Serrano JL (2004) Discotic liquid crystalline poly(propylene imine) dendrimers based on triphenylene. J Am Chem Soc 127:619–625

    Article  Google Scholar 

  • Mertesdorf C, Ringsdorf H (1989) Self-organization of substituted azacrowns based on their discoid and amphiphilic nature. Liq Cryst 5:1757–1772

    Article  Google Scholar 

  • Ogasawara M, Funahashi K, Iwata K (1985) Enhancement of electric conductivity of polypyrrole by stretching. Mol Cryst Liq Cryst 118:159–162

    Article  Google Scholar 

  • Orthmann E, Wegner G (1986) Preparation of ultrathin layers of molecularly controlled architecture from polymeric phthalocyanines by the Langmuir-Blodgett-technique. Angewandte Chem 25:1105–1107

    Article  Google Scholar 

  • Pal SK, Kumar S (2008) Novel triphenylene‐based ionic discotic liquid crystalline polymers. Liq Cryst 35:381–384

    Article  Google Scholar 

  • Percec V, Cho CG, Pugh C (1991) Alkyloxy-substituted CTTV derivatives that exhibit columnar mesophases. J Mater Chem 1:217–222

    Article  Google Scholar 

  • Percec V, Cho CG, Pugh C, Tomazos D (1992) Synthesis and characterization of branched liquid-crystalline polyethers containing cyclotetraveratrylene-based disk-like mesogens. Macromolecules 25:1164–1176

    Article  Google Scholar 

  • Picken S, Kouwer P, Jager W, Wübbenhorst M, Mijs W (2004) Dynamics and phase transitions in discotic and calamitic liquid crystal side-chain polymers. Mol Cryst Liq Cryst 411:503–513

    Article  Google Scholar 

  • Raja KS, Raghunathan VA, Ramakrishnan S (1998) Synthesis and properties of main chain discotic liquid crystalline polyethers based on Rufigallol. Macromolecules 31:3807–3814

    Article  Google Scholar 

  • Ringsdorf H, Tschirner P, Hermann-Schönherr O, Wendroff JH (1987) Synthesis, structure, and phase behaviour of liquid-crystalline rigid-rod polyesters and polyamides with disc-like mesogens in the main chain. Makromol Chem 188:1431–1445

    Article  Google Scholar 

  • Ringsdorf H, Wüstefeld R, Zerta E, Ebert M, Wendorff JH (1989) Induction of liquid crystalline phases: formation of discotic systems by doping amorphous polymers with electron acceptors. Angewandte Chem 28:914–918

    Article  Google Scholar 

  • Sauer T (1993) Hexagonal-columnar mesophases in substituted phthalocyaninato-polysiloxanes. Macromolecules 26:2057–2063

    Article  Google Scholar 

  • Sauer T, Wegner G (1991) Small-angle X-ray scattering from dilute solutions of substituted phthalocyaninato-polysiloxanes. Macromolecules 24:2240–2252

    Article  Google Scholar 

  • Schouten PG, Warman JM, De Haas MP, Van der Pol JF, Zwikker JW (1992) Radiation-induced conductivity in polymerized and nonpolymerized columnar aggregates of phthalocyanine. J Am Chem Soc 114:9028–9034

    Article  Google Scholar 

  • Sielcken OE, Van de Kuil LA, Drenth W, Schoonman J, Nolte RJM (1990) Phthalocyaninato polysiloxanes substituted with crown ether moieties. J Am Chem Soc 112:3086–3093

    Article  Google Scholar 

  • Sirlin C, Bosio L, Simon J (1987) Spinal columnar liquid crystals: polymeric octasubstituted [small micro]-oxo-(phthalocyaninato)tin(IV). J Chem Soc Chem Commun 5:379–380

    Article  Google Scholar 

  • Sirlin C, Bosio L, Simon J (1988a) Polycondensation in mesomorphic phases: spinal columnar liquid crystals based on octasubstituted phthalocyanine siloxane derivatives. Mol Cryst Liq Cryst Incorp Nonlinear Opt 155:231–238

    Article  Google Scholar 

  • Sirlin C, Bosio L, Simon J (1988b) Spinal columnar liquid crystals based on octasubstituted phthalocyanine siloxane derivatives. J Chem Soc Chem Commun 3:236–237

    Article  Google Scholar 

  • Stabel A, Herwig P, Müllen K, Rabe JP (1995) Diodelike current–voltage curves for a single molecule—tunneling spectroscopy with submolecular resolution of an alkylated, peri-condensed hexabenzocoronene. Angewandte Chem 34:1609–1611

    Article  Google Scholar 

  • Stewart D, Mchattie SG, Imrie TC (1998) Convenient synthesis of a discotic side group liquid crystal polymer. J Mater Chem 8:47–51

    Article  Google Scholar 

  • Stoeva Z, Lu Z, Ingram MD, Imrie CT (2013) A new polymer electrolyte based on a discotic liquid crystal triblock copolymer. Electrochim Acta 93:279–286

    Article  Google Scholar 

  • Suzuki D, Koide N (2001) Synthesis and Characterization of Biphenylethynylbenzene Type Discotic Liquid Crystal. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst 364:635–645

    Article  Google Scholar 

  • Talroze RV, Otmakhova OA, Koval MA, Kuptsov SA, Platé NA, Finkelmann H (2000) Acrylate based polymers and networks containing triphenylene groups: synthesis and structures. Macromol Chem Phys 201:877–881

    Article  Google Scholar 

  • Thunemann AF, Ruppelt D, Ito S, Mullen K (1999) Supramolecular architecture of a functionalized hexabenzocoronene and its complex with polyethyleneimine. J Mater Chem 9:1055–1057

    Article  Google Scholar 

  • Thunemann AF, Ruppelt D, Burger C, Mullen K (2000) Long-range ordered columns of a hexabenzo[bc, ef, hi, kl, no, qr]coronene-polysiloxane complex: towards molecular nanowires. J Mater Chem 10:1325–1329

    Article  Google Scholar 

  • Thünemann AF, Kubowicz S, Burger C, Watson MD, Tchebotareva N, Müllen K (2002) α-Helical-within-Discotic Columnar Structures of a Complex between Poly(ethylene oxide)-block-poly(l-lysine) and a Hexa-peri-hexabenzocoronene. J Am Chem Soc 125:352–356

    Article  Google Scholar 

  • Van der Pol JF, Neeleman E, Van Miltenburg JC, Zwikker JW, Nolte RJM, Drenth W (1990) A polymer with the mesomorphic order of liquid crystalline phthalocyanines. Macromolecules 23:155–162

    Article  Google Scholar 

  • Van Nostrum CF, Nolte RJM (1996) Functional supramolecular materials: self-assembly of phthalocyanines and porphyrazines. Chem Commun 21:2385–2392

    Article  Google Scholar 

  • van Nostrum CF, Picken SJ, Schouten A-J, Nolte RJM (1995) Synthesis and supramolecular chemistry of novel liquid crystalline crown ether-substituted phthalocyanines: toward molecular wires and molecular ionoelectronics. J Am Chem Soc 117:9957–9965

    Article  Google Scholar 

  • Vandevyver M, Albouy PA, Mingotaud C, Perez J, Barraud A, Karthaus O, Ringsdorf H (1993) In-plane anisotropy and phase change in Langmuir-Blodgett films of disklike molecules. Langmuir 9:1561–1567

    Article  Google Scholar 

  • Voigt-Martin IG, Garbella RW, Schumacher M (1992) Structure and defects in discotic crystals and liquid crystals as revealed by electron diffraction and high-resolution electron microscopy. Macromolecules 25:961–971

    Article  Google Scholar 

  • Valdebenito N, Oriol L, Barbera J, Díaz F, Serrano JL (2000) Liquid crystalline polymers containing discotic metallomesogens in the main chain. Macromol. Chem. Phys. 201, 2573–2580

    Google Scholar 

  • Wan W, Monobe H, Tanaka Y, Shimizu Y (2003) Mesomorphic properties of copolyesters of 3,6-linked triphenylene-based units and polymethylene spacers. Liq Cryst 30:571–578

    Article  Google Scholar 

  • Weck M, Mohr B, Maughon BR, Grubbs RH (1997) Synthesis of discotic columnar side-chain liquid crystalline polymers by Ring-Opening Metathesis Polymerization (ROMP). Macromolecules 30:6430–6437

    Article  Google Scholar 

  • Wenz G (1985) New polymers with disc-shaped mesogenic groups in the main chain. Makromol Chem Rapid Commun 6:577–584

    Article  Google Scholar 

  • Werth M, Spiess HW (1993) The role of the spacer in discotic polymers. Makromol Chem Rapid Commun 14:329–338

    Article  Google Scholar 

  • Wu B, Mu B, Wang S, Duan J, Fang J, Cheng R, Chen D (2013) Triphenylene-based side chain liquid crystalline block copolymers containing a PEG block: controlled synthesis, microphase structures evolution and their interplay with discotic mesogenic orders. Macromolecules 46:2916–2929

    Article  Google Scholar 

  • Xing C, Lam JWY, Zhao K, Tang BZ (2008) Synthesis and liquid crystalline properties of poly(1-alkyne)s carrying triphenylene discogens. J Polym Sci A Polym Chem 46:2960–2974

    Article  Google Scholar 

  • Zhang C, He Z, Mao H, Wang J, Wang D, Wang Y, Pu J (2007) Observation of disorder effects on charged carrier mobility in triphenylene-based discotic materials. J Lumin 123:931–935

    Article  Google Scholar 

  • Zimmermann H, Poupko R, Luz Z, Billard J (1988) Tetrabenzocyclododecatetraene A new core for mesogens exhibiting columnar mesophases. Liq Cryst 3:759–770

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Santanu Kumar Pal .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2016 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Singh, H., Kumar, S., Pal, S.K. (2016). Discotic Liquid Crystalline Polymers: Structure and Chemistry. In: Thakur, V., Kessler, M. (eds) Liquid Crystalline Polymers. Springer, Cham. https://doi.org/10.1007/978-3-319-22894-5_20

Download citation

Publish with us

Policies and ethics