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Fullerene Liquid Crystals

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Polymers and Polymeric Composites: A Reference Series

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Abstract

Fullerene-based liquid crystalline materials contain both the excellent optical and electrical properties of fullerene and the self-organization and external-field-responsive properties of liquid crystals (LCs). They have potential applications in optical and photovoltaic devices, organic field-effect transistors, especially as active materials in polymer solar cells. Here, we have summarized the results on the design strategies for [60]fullerene LCs into two approaches, namely, the molecular LC approach and the supramolecular LC approach, respectively. The molecular LC approach is introduced first to design [60]fullerene LCs via a traditional way, where C60 was linked together with large liquid crystal mesogens to give nematic, cholesteric, smectic, and columnar phases of LCs by the Bingel reaction or the 1,3-dipolar cycloaddition reaction. This strategy needs large mesogens to fulfill the molecular aspect ratio of LCs. Thus the content of C60 is low, usually less than 20%, and the properties from fullerene are hindered. Another approach is via the supramolecular self-assembly, where the [60]fullerene derivatives self-assemble to form supramolecular structure which meets the aspect ratio requirements of liquid crystals. The supramolecular LC approach opens up new strategies to design liquid crystals with low molecular aspect ratio, enabling high [60]fullerene content in the supramolecular LCs. Some of the interesting properties form [60]fullerene LCs are also summarized, especially the electrochemical properties, the chiral properties, the light emitting properties, and the optoelectronic properties. Among them, high fullerene content is the key for these LCs to achieve good properties.

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References

  • Allard E, Oswald F, Donnio B, Guillon D, Delgado JL, Langa F, Deschenaux R (2005) Liquid-crystalline [60]fullerene-TTF dyads. Org Lett 7:383–386

    Article  CAS  Google Scholar 

  • André D, Dworkin A, Szwarc H, Céolin R, Agafonov V, Fabre C, Rassat A, Straver L, Bernier P, Zahab A (1992) Molecular packing of fullerene C60 at room temperature. Mol Phys 76:1311–1317

    Article  Google Scholar 

  • Andreas H, Michael B, Fred W (2005) Fullerenes: chemistry and reactions. Wiley-VCH, Weinheim

    Google Scholar 

  • Anthopoulos TD, Singh B, Marjanovic N, Sariciftci NS, Montaigne Ramil A, Sitter H, Cölle M, de Leeuw DM (2006) High performance n-channel organic field-effect transistors and ring oscillators based on C60 fullerene films. Appl Phys Lett 89:213504

    Article  Google Scholar 

  • Bushby RJ, Hamley IW, Liu Q, Lozman OR, Lydon JE (2005) Self-assembled columns of fullerene. J Mater Chem 15:4429–4434

    Article  CAS  Google Scholar 

  • Campidelli S, Deschenaux R, Eckert J-F, Guillon D, Nierengarten J-F (2002) Liquid-crystalline fullerene-oligophenylenevinylene conjugates. Chem Commun 6:656–657

    Article  Google Scholar 

  • Campidelli S, Eng C, Saez IM, Goodby JW, Deschenaux R (2003) Functional polypedes-chiral nematic fullerenes. Chem Commun 13:1520–1521

    Article  Google Scholar 

  • Campidelli S, Vázquez E, Milic D, Prato M, Barberá J, Guldi DM, Marcaccio M, Paolucci D, Paolucci F, Deschenaux R (2004) Liquid-crystalline fullerene-ferrocene dyads. J Mater Chem 14:1266–1272

    Article  CAS  Google Scholar 

  • Campidelli S, Lenoble J, Barberá J, Paolucci F, Marcaccio M, Paolucci D, Deschenaux R (2005) Supramolecular fullerene materials: dendritic liquid-crystalline fulleropyrrolidines. Macromolecules 38:7915–7925

    Article  CAS  Google Scholar 

  • Campidelli S, Brandmuller T, Hirsch A, Saez IM, Goodby JW, Deschenaux R (2006a) An optically-active liquid-crystalline hexa-adduct of [60]fullerene which displays supramolecular helical organization. Chem Commun 41:4282–4284

    Article  Google Scholar 

  • Campidelli S, Pérez L, Rodríguez-López J, Barberá J, Langa F, Deschenaux R (2006b) Dendritic liquid-crystalline fullerene-ferrocene dyads. Tetrahedron 62:2115–2122

    Article  CAS  Google Scholar 

  • Campidelli S, Séverac M, Scanu D, Deschenaux R, Vázquez E, Milic D, Prato M, Carano M, Marcaccio M, Paolucci F, Rahman GMA, Guldi DM (2008) Photophysical, electrochemical, and mesomorphic properties of a liquid-crystalline [60]fullerene–peralkylated ferrocene dyad. J Mater Chem 18:1504–1509

    Article  CAS  Google Scholar 

  • Campidelli S, Bourgun P, Guintchin B, Furrer J, Stoeckli-Evans H, Saez IM, Goodby JW, Deschenaux R (2010) Diastereoisomerically pure fulleropyrrolidines as chiral platforms for the design of optically active liquid crystals. J Am Chem Soc 132:3574–3581

    Article  CAS  Google Scholar 

  • Carano M, Chuard T, Deschenaux R, Even M, Marcaccio M, Paolucci F, Prato M, Roffia S (2002) Electrochemical properties of a liquid-crystalline mixed fullerene-ferrocene material and related species. J Mater Chem 12:829–833

    Article  CAS  Google Scholar 

  • Chuard T, Deschenaux R (1996) First fullerene[60]-containing thermotropic liquid crystal. Preliminary communication. Helv Chim Acta 79:736–741

    Article  CAS  Google Scholar 

  • Chuard T, Deschenaux R (2002) Design, mesomorphic properties, and supramolecular organization of [60]fullerene-containing thermotropic liquid crystals. J Mater Chem 12:1944–1951

    Article  CAS  Google Scholar 

  • Chuard T, Deschenaux R, Hirsch A, Schönberger H (1999) A liquid-crystalline hexa-adduct of [60]fullerene. Chem Commun 20:2103–2104

    Article  Google Scholar 

  • Chuard T, Dardel B, Deschenaux R, Even M (2000) [60]fullerene-containing thermotropic liquid crystals. Carbon 38:1573–1576

    Article  CAS  Google Scholar 

  • Dardel B, Deschenaux R, Even M, Serrano E (1999) Synthesis, characterization, and mesomorphic properties of a mixed [60]fullerene-ferrocene liquid-crystalline dendrimer. Macromolecules 32:5193–5198

    Article  CAS  Google Scholar 

  • Dardel B, Guillon D, Heinrich B, Deschenaux R (2001) Fullerene-containing liquid-crystalline dendrimer. J Mater Chem 11:2814–2831

    Article  CAS  Google Scholar 

  • Deschenaux R, Even M, Guillon D (1998) Liquid-crystalline mixed [60]fullerene-ferrocene materials. Chem Commun 5:537–538

    Article  Google Scholar 

  • Deschenaux R, Donnio B, Guillon D (2007) Liquid-crystalline fullerodendrimers. New J Chem 31:1064–1073

    Article  CAS  Google Scholar 

  • Even M, Heinrich B, Guillon D, Guldi DM, Prato M, Deschenaux R (2001) A mixed fullerene-ferrocene thermotropic liquid crystal: synthesis, liquid-crystalline properties, supramolecular organization and photoinduced electron transfer. Chem Eur J 7:2595–2604

    Article  CAS  Google Scholar 

  • Felder D, Heinrich B, Guillon D, Nicoud JF, Nierengarten JF (2000) A liquid crystalline supramolecular complex of C60 with a cyclotriveratrylene derivative. Chem Eur J 6:3501–3507

    Article  CAS  Google Scholar 

  • Felder-Flesch D, Rupnicki L, Bourgogne C, Donnio B, Guillon D (2006) Liquid-crystalline cholesterol-based [60]fullerene hexaadducts. J Mater Chem 16:304–309

    Article  CAS  Google Scholar 

  • Fernandes PA, Yagai S, Mohwald H, Nakanishi T (2010) Molecular arrangement of alkylated fullerenes in the liquid crystalline phase studied with X-ray diffraction. Langmuir 26:4339–4345

    Article  CAS  Google Scholar 

  • Hayashi H, Nihashi W, Umeyama T, Matano Y, Seki S, Shimizu Y, Imahori H (2011) Segregated donor-acceptor columns in liquid crystals that exhibit highly efficient ambipolar charge transport. J Am Chem Soc 133:10736–10739

    Article  CAS  Google Scholar 

  • Heiney PA (1992) Structure, dynamics and ordering transition of solid C60. J Phys Chem Solids 53:1333–1352

    Article  CAS  Google Scholar 

  • Kadish KM, Ruoff RS (2000) Fullerenes: chemistry, physics, and technology. Wiley-Interscience, New York

    Google Scholar 

  • Kimura M, Saito Y, Ohta K, Hanabusa K, Shirai H, Kobayashi N (2002) Self-organization of supramolecular complex composed of rigid dendritic porphyrin and fullerene. J Am Chem Soc 124:5274–5275

    Article  CAS  Google Scholar 

  • Lehmann M, Hugel M (2015) A perfect match: fullerene guests in star-shaped oligophenylenevinylene mesogens. Angew Chem Int Ed 54:4110–4114

    Article  CAS  Google Scholar 

  • Lenoble J, Maringa N, Campidelli S, Donnio B, Guillon D, Deschenaux R (2006) Liquid-crystalline fullerodendrimers which display columnar phases. Org Lett 8:1851–1854

    Article  CAS  Google Scholar 

  • Li WS, Yamamoto Y, Fukushima T, Saeki A, Seki S, Tagawa S, Masunaga H, Sasaki S, Takata M, Aida T (2008) Amphiphilic molecular design as a rational strategy for tailoring bicontinuous electron donor and acceptor arrays: photoconductive liquid crystalline oligothiophene-C60 dyads. J Am Chem Soc 130:8886–8887

    Article  CAS  Google Scholar 

  • Li CZ, Matsuo Y, Nakamura E (2010) Octupole-like supramolecular aggregates of conical iron fullerene complexes into a three-dimensional liquid crystalline lattice. J Am Chem Soc 132:15514–15515

    Article  CAS  Google Scholar 

  • Liu Y, Zhao J, Li Z, Mu C, Ma W, Hu H, Jiang K, Lin H, Ade H, Yan H (2014) Aggregation and morphology control enables multiple cases of high-efficiency polymer solar cells. Nat Commun 5:5293

    Article  CAS  Google Scholar 

  • Mamlouk H, Heinrich B, Bourgogne C, Donnio B, Guillon D, Felder-Flesch D (2007) A nematic [60]fullerene supermolecule: when polyaddition leads to supramolecular self-organization at room temperature. J Mater Chem 17:2199–2205

    Article  CAS  Google Scholar 

  • Matsuo Y, Muramatsu A, Hamasaki R, Mizoshita N, Kato T, Nakamura E (2004) Stacking of molecules possessing a fullerene apex and a cup-shaped cavity connected by a silicon connection. J Am Chem Soc 126:432–433

    Article  CAS  Google Scholar 

  • Matsuo Y, Muramatsu A, Kamikawa Y, Kato T, Nakamura E (2006) Synthesis and structural, electrochemical, and stacking properties of conical molecules possessing buckyferrocene on the apex. J Am Chem Soc 128:9586–9587

    Article  CAS  Google Scholar 

  • Nakanishi T, Shen Y, Wang J, Yagai S, Funahashi M, Kato T, Fernandes P, Mohwald H, Kurth DG (2008) Electron transport and electrochemistry of mesomorphic fullerenes with long-range ordered lamellae. J Am Chem Soc 130:9236–9237

    Article  CAS  Google Scholar 

  • Orlandi S, Muccioli L, Ricci M, Zannoni C (2009) Self assembled fullerene walls in di-mesogenic-C60 materials. Soft Matter 5:4484–4491

    Article  CAS  Google Scholar 

  • Perez L, Lenoble J, Barbera J, de la Cruz P, Deschenaux R, Langa F (2008) [60]fullerene-based liquid crystals acting as acid-sensitive fluorescent probes. Chem Commun 38:4590–4592

    Article  Google Scholar 

  • Sawamura M, Kawai K, Matsuo Y, Kanie K, Kato T, Nakamura E (2002) Stacking of conical molecules with a fullerene apex into polar columns in crystals and liquid crystals. Nature 419:702–705

    Article  CAS  Google Scholar 

  • Tirelli N, Cardullo F, Habicher T, Suter UW, Diederich F (2000) Thermotropic behaviour of covalent fullerene adducts displaying 4-cyano-4′-oxybiphenyl mesogens. J Chem Soc Perkin Trans (2):193–198

    Google Scholar 

  • Vergara J, Barbera J, Serrano JL, Ros MB, Sebastian N, de la Fuente R, Lopez DO, Fernandez G, Sanchez L, Martin N (2011) Liquid-crystalline hybrid materials based on [60]fullerene and bent-core structures. Angew Chem Int Ed 50:12523–12528

    Article  CAS  Google Scholar 

  • Wang CL, Zhang WB, Sun HJ, Van Horn RM, Kulkarni RR, Tsai CC, Hsu CS, Lotz B, Gong X, Cheng SZD (2012) A supramolecular “double-cable” structure with a 12944 Helix in a columnar porphyrin-C60 dyad and its application in polymer solar cells. Adv Energy Mater 2:1375–1382

    Article  CAS  Google Scholar 

  • Zhang X, Hsu CH, Ren X, Gu Y, Song B, Sun HJ, Yang S, Chen E, Tu Y, Li X, Yang X, Li Y, Zhu X (2015) Supramolecular [60]fullerene liquid crystals formed by self-organized two-dimensional crystals. Angew Chem Int Ed 54:114–117

    Article  CAS  Google Scholar 

  • Zhong YW, Matsuo Y, Nakamura E (2007) Lamellar assembly of conical molecules possessing a fullerene apex in crystals and liquid crystals. J Am Chem Soc 129:3052–3053

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China

    Xiaoming Yang, Tiantian Zhu & Yingfeng Tu

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  1. Xiaoming Yang
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  2. Tiantian Zhu
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  3. Yingfeng Tu
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Correspondence to Yingfeng Tu .

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Editors and Affiliations

  1. Indian Institute of Technology-Roorkee, Saharanpur, India

    Sanjay Palsule

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Yang, X., Zhu, T., Tu, Y. (2018). Fullerene Liquid Crystals. In: Palsule, S. (eds) Polymers and Polymeric Composites: A Reference Series. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-37179-0_62-1

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  • DOI: https://doi.org/10.1007/978-3-642-37179-0_62-1

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  • Print ISBN: 978-3-642-37179-0

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