Fluorine-containing triphenylenes. Liquid crystalline properties and surface ordering

References

• Adam D, Schuhmacher P, Simmerer J, Häussling L, Siemensmeyer K, Etzbach KH, Ringsdorf H, Haarer D. Fast photoconduction in the highly ordered columnar phase of a discotic liquid crystal. Nature. 1994;371:141–143.
   Web of Science ®Google Scholar
• Van De Craats AM, Warman JM, De Haas MP, Adam D, Simmerer J, Haarer D, Schuhmacher P. 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. 1996;8:823–826. doi:10.1002/adma.19960081012.
   Web of Science ®Google Scholar
• Struijk CW, Sieval AB, Dakhorst JEJ, Van Dijk M, Kimkes P, Koehorst RBM, Donker H, Schaafsma TJ, Picken SJ, Van De Craats AM, Warman JM, Zuilhof H, Sudhölter EJR. Liquid crystalline perylene diimides: architecture and charge carrier mobilities. J Am Chem Soc. 2000;122:11057–11066. doi:10.1021/ja000991g.
   Web of Science ®Google Scholar
• Kumar S. Recent developments in the chemistry of triphenylene-based discotic liquid crystals. Liq Cryst. 2004;31:1037–1059. doi:10.1080/02678290410001724746.
   Web of Science ®Google Scholar
• Kumar S. Triphenylene based discotic liquid crystal dimers, oligomers and polymers. Liq Cryst. 2005;32:1089–1113. doi:10.1080/02678290500117415.
   Web of Science ®Google Scholar
• Laschat S, Baro A, Steinke N, Giesselmann F, Hägele C, Scalia G, Judele R, Kapatsina E, Sauer S, Schreivogel A, Tosoni M. Discotic liquid crystals: from tailor-made synthesis to plastic electronics. Angew Chem Int Ed. 2007;46:4832–4887. doi:10.1002/anie.200604203.
   PubMed Web of Science ®Google Scholar
• Sergeyev S, Pisula W, Geerts YH. Discotic liquid crystals: a new generation of organic semiconductors. Chem Soc Rev. 2007;36:1902–1929. doi:10.1039/b417320c.
   PubMed Web of Science ®Google Scholar
• Pisula W, Zorn M, Chang JY, Müllen K, Zentel R. Liquid crystalline ordering and charge transport in semiconducting materials. Macromol Rapid Commun. 2009;30:1179–1202. doi:10.1002/marc.200900251.
   PubMed Web of Science ®Google Scholar
• Kaafarani BR. Discotic liquid crystals for opto-electronic applications. Chem Mater. 2011;23:378–396. doi:10.1021/cm102117c.
   Web of Science ®Google Scholar
• Pal SK, Setia S, Avinash BS, Kumar S. Triphenylene-based discotic liquid crystals: recent advances. Liq Cryst. 2013;40:1769–1816.
   Web of Science ®Google Scholar
• Schmidt-Mende L, Fechtenkötter A, Müllen K, Moons E, Friend RH, MacKenzie JD. Self-organized discotic liquid crystals for high-efficiency organic photovoltaics. Science. 2001;293:1119–1122. doi:10.1126/science.293.5532.1119.
   PubMed Web of Science ®Google Scholar
• Hori T, Miyake Y, Yamasaki N, Yoshida H, Fujii A, Shimizu Y, Ozaki M. Solution processable organic solar cell based on bulk heterojunction utilizing phthalocyanine derivative. Appl Phys Express. 2010;3:101602.
   Web of Science ®Google Scholar
• Kang SJ, Ahn S, Kim JB, Schenck C, Hiszpanski AM, Oh S, Schiros T, Loo Y-L, Nuckolls C. Using self-organization to control morphology in molecular photovoltaics. J Am Chem Soc. 2013;135:2207–2212. doi:10.1021/ja308628z.
   PubMed Web of Science ®Google Scholar
• Shimizu Y, Oikawa K, Nakayama K-I, Guillon D. Mesophase semiconductors in field effect transistors. J Mater Chem. 2007;17:4223–4229. doi:10.1039/b705534j.
   Web of Science ®Google Scholar
• Funahashi M. Development of liquid-crystalline semiconductors with high Carrier mobilities and their application to thin-film transistors. Polym J. 2009;41:459–469. doi:10.1295/polymj.PJ2008324.
   Web of Science ®Google Scholar
• Hassheider T, Benning SA, Kitzerow H-S, Achard M-F, Bock H. Color-tuned electroluminescence from columnar liquid crystalline alkyl arenecarboxylates. Angew Chem Int Ed. 2001;40:2060–2063. doi:10.1002/1521-3773(20010601)40:11<2060::AID-ANIE2060>3.0.CO;2-H.
   PubMed Web of Science ®Google Scholar
• Diring S, Camerel F, Donnio B, Dintzer T, Toffanin S, Capelli R, Muccini M, Ziessel R. Luminescent ethynyl-pyrene liquid crystals and gels for optoelectronic devices. J Am Chem Soc. 2009;131:18177–18185.
   PubMed Web of Science ®Google Scholar
• Hird M. Fluorinated liquid crystals - properties and applications. Chem Soc Rev. 2007;36:2070–2095. doi:10.1039/b610738a.
   PubMed Web of Science ®Google Scholar
• Tschierske C. Liquid crystal engineering - New complex mesophase structures and their relations to polymer morphologies, nanoscale patterning and crystal engineering. Chem Soc Rev. 2007;36:1930–1970. doi:10.1039/b615517k.
   PubMed Web of Science ®Google Scholar
• Tschierske C. Fluorinated liquid crystals: design of soft nanostructures and increased complexity of self-assembly by perfluorinated segments. Top Curr Chem. 2012;318:1–108. doi:10.1007/128_2011_267.
   PubMed Web of Science ®Google Scholar
• Dahn U, Erdelen C, Ringsdorf H, Festag R, Wendorff JH, Heiney PA, Maliszewskyj NC. Fluoroalkylated discotic liquid crystals. Liq Cryst. 1995;19:759–764. doi:10.1080/02678299508031096.
   Web of Science ®Google Scholar
• Terasawa N, Monobe H, Kiyohara K, Shimizu Y. Strong tendency towards homeotropic alignment in a hexagonal columnar mesophase of fluoroalkylated triphenylenes. Chem Commun. 2003;9:1678–1679. doi:10.1039/b304512a.
   Web of Science ®Google Scholar
• Terasawa N, Monobe H, Kiyohara K, Shimizu Y. Fluorination effect of the peripheral chains on the mesomorphic properties in discotic liquid crystals of hexasubstituted triphenylene. Chem Lett. 2003;32:214–215.
   Web of Science ®Google Scholar
• Terasawa N, Monobe H, Kiyohara K. Mesomorphic phase transition behavior of novel triphenylene compounds possessing fluoroalkylated side chains. J Fluor Chem. 2006;127:954–961. doi:10.1016/j.jfluchem.2006.04.011.
   Web of Science ®Google Scholar
• Terasawa N, Monobe H, Kiyohara K. Mesomorphic properties of symmetrical and asymmetrical triphenylene homologues possessing fluoroalkylated side chains. Liq Cryst. 2007;34:311–324. doi:10.1080/02678290601104817.
   Web of Science ®Google Scholar
• Yang G, Zhao K, Yu W, Hu P, Wang B. Synthesis of unsymmetric triphenylene discotic liquid crystals with a semi-fluorinated chain and the influence of fluorophobic effect on mesogenic behavior. Sci China Ser B: Chem. 2009;52:1244–1252. doi:10.1007/s11426-009-0113-0.
   Google Scholar
• Chen H-M, Zhao K-Q, Wang L, Hu P, Wang B-Q. Synthesis and mesomorphism of triphenylene discotic liquid crystals containing fluorinated chains. Soft Materials. 2011;9:359–381. doi:10.1080/1539445X.2010.525444.
   Web of Science ®Google Scholar
• Terasawa N, Tanigaki N, Monobe H, Kiyohara K. Alignment behavior for novel triphenylene compounds possessing fluoroalkylated side chains on modified substrates. J Fluor Chem. 2006;127:1096–1104. doi:10.1016/j.jfluchem.2006.05.016.
   Web of Science ®Google Scholar
• Terasawa N, Monobe H. Alignment behaviour of symmetrical and asymmetrical triphenylenes possessing fluoroalkylated side chains on modified substrates. Liq Cryst. 2007;34:447–455. doi:10.1080/02678290701211520.
   Web of Science ®Google Scholar
• Wang J, He Z, Zhang Y, Zhao H, Zhang C, Kong X, Mu L, Liang C. The driving force for homeotropic alignment of a triphenylene derivative in a hexagonal columnar mesophase on single substrates. Thin Solid Films. 2010;518:1973–1979.
   Web of Science ®Google Scholar
• De Cupere V, Tant J, Viville P, Lazzaroni R, Osikowicz W, Salaneck WR, Geerts YH. Effect of interfaces on the alignment of a discotic liquid-crystalline phthalocyanine. Langmuir. 2006;22:7798–7806.
   PubMed Web of Science ®Google Scholar
• Grelet E, Bock H. Control of the orientation of thin open supported columnar liquid crystal films by the kinetics of growth. Europhys Lett. 2006;73:712–718. doi:10.1209/epl/i2005-10459-5.
   Google Scholar
• Schweicher G, Gbabode G, Quist F, Debever O, Dumont N, Sergeyev S, Geerts YH. Homeotropic and planar alignment of discotic liquid crystals: the role of the columnar mesophase. Chem Mater. 2009;21:5867–5874.
   Web of Science ®Google Scholar
• Sergeyev S, Levin J, Balandier J-Y, Pouzet E, Geerts YH. Homeotropic alignment in films of a mesogenic phthalocyanine depends on the nature of interactions with the surface. Mendeleev Commun. 2009;19:185–186. doi:10.1016/j.mencom.2009.07.003.
   Web of Science ®Google Scholar
• Paraschiv I, Delforterie P, Giesbers M, Posthumus MA, Marcelis ATM, Zuilhof H, Sudhölter EJR. Asymmetry in liquid crystalline hexaalkoxytriphenylene discotics. Liq Cryst. 2005;32:977–983. doi:10.1080/02678290500286913.
   Web of Science ®Google Scholar
• Paraschiv I, Giesbers M, Van Lagen B, Grozema FC, Abellon RD, Siebbeles LDA, Marcelis ATM, Zuilhof H, Sudhölter EJR. H-bond-stabilized triphenylene-based columnar discotic liquid crystals. Chem Mater. 2006;18:968–974. doi:10.1021/cm052221f.
   Web of Science ®Google Scholar
• Paraschiv I, De Lange K, Giesbers M, Van Lagen B, Grozema FC, Abellon RD, Siebbeles LDA, Sudhölter EJR, Zuilhof H, Marcelis ATM. Hydrogen-bond stabilized columnar discotic benzenetrisamides with pendant triphenylene groups. J Mater Chem. 2008;18:5475–5481. doi:10.1039/b805283b.
   Web of Science ®Google Scholar
• Miyake Y, Fujii A, Ozaki M, Shimizu Y. Carrier mobility of a columnar mesophase formed by a perfluoroalkylated triphenylene. Synthetic Met. 2009;159:875–879.
   Google Scholar
• McKenna MD, Barberá J, Marcos M, Serrano JL. Discotic liquid crystalline poly(propylene imine) dendrimers based on triphenylene. J Am Chem Soc. 2005;127:619–625. doi:10.1021/ja0455906.
   PubMed Web of Science ®Google Scholar
• Imrie CT, Inkster RT, Lu Z, Ingram MD. Discotic side group liquid crystal polymer electrolytes. Mol Cryst Liq Cryst. Synthesis. 2004;408:33–43.
   Web of Science ®Google Scholar
• Naarmann H, Hanack M, Mattmer R. A high yield easy method for the preparation of alkoxy-substituted triphenylenes. Synthesis. 1994;1:477–478.
   Google Scholar
• Li Y, Giesbers M, Gerth M, Zuilhof H. Generic top-functionalization of patterned antifouling zwitterionic polymers on indium tin oxide. Langmuir. 2012;28:12509–12517.
   PubMed Web of Science ®Google Scholar
• Oswald P, Pieranski P. Smectic and columnar liquid crystals. Boca Raton, FL: Taylor & Francis; 2006.
   Google Scholar