347
Views
9
CrossRef citations to date
0
Altmetric
Invited Article

Phase behaviour of star-shaped binary mixtures of triphenylbenzenes, triphenylboroxines and triphenyltriazines

, , , &
Pages 1973-1984 | Received 28 Feb 2019, Published online: 21 May 2019

References

  • Geelhaar T, Griesar K, Reckmann B. 125 years of liquid crystals-a scientific revolution in the home. Angew Chem Int Ed. 2013;52:8798–8809.
  • Bremer M, Kirsch P, Klasen-Memmer M, et al. The TV in your pocket: development of liquid-crystal materials for the new millennium. Angew Chem Int Ed. 2013;52:8880–8896.
  • Wöhrle T, Wurzbach I, Kirres J, et al. Discotic liquid crystals. Chem Rev. 2016;116:1139–1241.
  • Laschat S, Baro A, Steinke N, et al. Discotic liquid crystals: from Tailor-made synthesis to plastic electronics. Angew Chem Int Ed. 2007;46:4832–4887.
  • Sergeyev S, Pisula W, Geerts YH. Discotic liquid crystals: a new generation of organic semiconductors. Chem Soc Rev. 2007;36:1902–1929.
  • Booth CJ, Krüerke D, Heppke G. Highly twisting enantiomeric radial multiyne dopants for discotic liquid-crystalline systems. J Mater Chem. 1996;6:927–934.
  • Kreouzis T, Scott K, Donovan KJ, et al. Enhanced electronic transport properties in complementary binary discotic liquid crystal systems. Chem Phys. 2000;262:489–497.
  • Boden N, Bushby RJ, Cooke G, et al. CPI: a recipe for improving applicable properties of discotic liquid crystals. J Am Chem Soc. 2001;123:7915–7916.
  • Pecchia A, Lozman OR, Movaghar B, et al. Photoconductive transients and one-dimensional charge carrier dynamics in discotic liquid crystals. Phys Rev B. 2002;65:104204-1–104204-10.
  • Wegewijs BR, Siebbeles LDA, Boden N, et al. Charge-carrier mobilities in binary mixtures of discotic triphenylene derivatives as a function of temperature. Phys Rev B. 2002;65:245112-1–245112-8.
  • Boden N, Bushby R, Lozman O. A comparison of CPI and charge-transfer two-component columnar phases. Mol Cryst Liq Cryst. 2004;411:345–354.
  • Khan AA, Rughoobur G, Kamarudin MA, et al. Homologous binary mixtures and improved hole conduction of self-assembled discotic liquid crystals. Org Electron. 2016;36:35–44.
  • An L, Jing M, Xiao B, et al. Phase behaviors of binary mixtures composed of electron-rich and electron-poor triphenylene discotic liquid crystals. Chin Phys B. 2016;25:096402.
  • Yildirim Z, Mendes E, Picken SJ, et al. Binary phase diagram of triphenylene derivatives: the role of hydrogen bonds. Mol Cryst Liq Cryst. 2005;439:237/[2103]–243/[2109].
  • Vogel L, Janietz D, Prehm M, et al. Polyphilic hydrogen bonded block molecules involving semiperfluorinated and silylated molecular fragments. Soft Matter. 2017;13:7188–7196.
  • Kohlmeier A, Vogel L, Janietz D. Multiple hydrogen bonded mesomorphic complexes between complementary 1,3,5-triazine and pyrimidine derivatives. Soft Matter. 2013;9:9476–9486.
  • Bé AG, Tran C, Sechrist R, et al. Strongly dichroic organic films via controlled assembly of modular aromatic charge-transfer liquid crystals. Org Lett. 2015;17:4834–4837.
  • Wu S-H, Chen H-H. Self-assembling behavior of binary mixture of hexa-peri-hexabenzocoronene derivatives with different molecular symmetry. Tetrahedron. 2019;75:220–229.
  • Schweicher G, Gbabode G, Quist F, et al. Homeotropic and planar alignment of discotic liquid crystals: the role of the columnar mesophase. Chem Mater. 2009;21:5867–5874.
  • Sergeyev S, Debever O, Pouzet E, et al. Transition temperature engineering of octaalkoxycarbonyl phthalocyanines. J Mater Chem. 2007;17:3002–3007.
  • Tant J, Geerts YH, Lehmann M, et al. Liquid crystalline metal-free phthalocyanines designed for charge and exciton transport. J Phys Chem B. 2005;109:20315–20323.
  • Nakagawa D, Nakano C, Ohmori M, et al. Miscibility and carrier transport properties in binary blend system of non-peripherally octa-hexyl-substituted phthalocyanine analogues. Org Electron. 2017;44:67–73.
  • Shimizu Y, Matsuda Y, Nekelson F, et al. Binary systems of discotic liquid crystalline semiconductors toward solution-processing thin film devices. Proc of SPIE. 2012;8279:82790G-1–82790G-8.
  • Taing H, Rothera JG, Binder JF, et al. 1,3,5-triazine(trithiophenylcarboxylate) esters form metastable monotropic nematic discotic liquid crystal phases. Liq Cryst. 2018;45:1147–1154.
  • Cinacchi G, Tani A. Computer simulations of pure and mixed systems of disklike particles interacting with the S-function corner potential. J Chem Phys. 2002;117:11388–11395.
  • Koda T, Nishioka A, Ikeda S. Computer simulation of binary mixtures of anisotropic hard particles. J Phys Condens Matter. 2005;17:2875–2878.
  • Cienega-Cacerez O, García-Alcántara C, Moreno-Razo JA, et al. Induced stabilization of columnar phases in binary mixtures of discotic liquid crystals. Soft Matter. 2016;12:1295–1312.
  • Lehmann M. Star-shaped mesogens. In: Goodby JW, Tschierske C, Raynes P, et al., editors. Handbook of liquid crystals. Weinheim, Germany: Wiley-VCH; 2014. p. 1–73.
  • Lehmann M. Star-shaped mesogens – hekates: the most basic star structure with three branches. In: Tschierske C, editors. Liquid crystals. Berlin, Heidelberg: Springer; 2011. p. 193–223.
  • Lehmann M. Star mesogens (Hekates)-Tailor-made molecules for programming supramolecular functionality. Chem Eur J. 2009;15:3638–3651.
  • Lehmann M, Schartel B, Hennecke M, et al. Dendrimers consisting of stilbene or distyrylbenzene building blocks synthesis and stability. Tetrahedron. 1999;55:13377–13394.
  • Roth S, Lehmann M. Mesogenic origami – four-armed, star-shaped mesogens as precursors for functional liquid crystal materials. Liq Cryst. 2017;1–22.
  • Umesh CP, Gangarapu S, Marcelis ATM, et al. Discotic liquid crystalline tris(hexahexyloxytriphenylene)triazines with separate columns of triphenylene and triazine cores. Liq Cryst. 2014;41:1862–1872.
  • Cammidge AN, King ASH. Model studies towards liquid crystalline dendrimers with mesogenic repeat units throughout the structure. Tetrahedron Lett. 2006;47:5569–5572.
  • Yang F, Xie J, Guo H, et al. Novel discotic liquid crystal oligomers: 1,3,5-triazine-based triphenylene dimer and trimer with wide mesophase. Liq Cryst. 2012;39:1368–1374.
  • Lehmann M, Jahr M, Gutmann J. Star-shaped oligobenzoates with a naphthalene chromophore as potential semiconducting liquid crystal materials? J Mater Chem. 2008;18:2995.
  • Lehmann M, Jahr M, Grozema FC, et al. Columnar mesophases with 3D order from new functional nonconventional star-shaped mesogens. Adv Mater. 2008;20:4414–4418.
  • Lehmann M, Jahr M, Donnio B, et al. Star-shaped oligobenzoates: non-conventional mesogens forming columnar helical mesophases. Chem Eur J. 2008;14:3562–3576.
  • Weber CHM, Liu F, Zeng X, et al. Body-centered cubic phase in 3-arm star mesogens: a torsional tapping AFM and GISAXS study. Soft Matter. 2010;6:5390.
  • Simalou O, Xue P, Lu R. A potent triphenylbenzene-based H-bonding donor to assist formation of two-component organogels with stilbazoles. Tetrahedron Lett. 2010;51:3685–3690.
  • Bao C, Jin M, Lu R, et al. Clockwise helical stacking of triphenylbenzene-based organogelator induced by peripheral chirality. Tetrahedron. 2007;63:7443–7448.
  • Tominaga M, Masu H, Katagiri K, et al. Triple helical structure constructed by covalent bondings: effective synthesis by a pre-organized partial structure and helicity induced by aromatic–aromatic interactions. Tetrahedron Lett. 2007;48:4369–4372.
  • Bao C, Lu R, Jin M, et al. Helical stacking tuned by alkoxy side chains in π-conjugated triphenylbenzene discotic derivatives. Chem Eur J. 2006;12:3287–3294.
  • Bae J, Kim J-K, Oh N-K, et al. Organization of rigid wedge−flexible coil block copolymers into liquid crystalline assembly. Macromolecules. 2005;38:4226–4230.
  • Kim J-K, Hong M-K, Ahn J-H, et al. Liquid-crystalline assembly from rigid wedge-flexible coil diblock molecules. Angew Chem Int Ed. 2005;44:328–332.
  • Jang C-J, Ryu J-H, Lee J-D, et al. Synthesis and supramolecular nanostructure of amphiphilic rigid aromatic-flexible dendritic block molecules. Chem Mater. 2004;16:4226–4231.
  • Pathak SK, Gupta RK, Nath S, et al. Columnar self-assembly of star-shaped luminescent oxadiazole and thiadiazole derivatives. J Mater Chem C. 2015;3:2940–2952.
  • Metzroth T, Hoffmann A, Martín-Rapún R, et al. Unravelling the fine structure of stacked bipyridine diamine-derived C 3 -discotics as determined by X-ray diffraction, quantum-chemical calculations, fast-MAS NMR and CD spectroscopy. Chem Sci. 2011;2:69–76.
  • Bader K, Wöhrle T, Öztürk E, et al. Encapsulating propeller-like columnar liquid crystals with an aromatic outer shell: influence of phenoxy-terminated side chains on the phase behaviour of triphenylbenzenes. Soft Matter. 2018;14:6409–6414.
  • Obsiye A, Wöhrle T, Haenle JC, et al. Dendrimeric triphenylbenzenes: helical versus zig-zag arrangement in columnar mesophases. Liq Cryst. 2018;45:164–172.
  • Lehmann M, Hügel M, Perfect Match: A. Fullerene guests in star-shaped oligophenylenevinylene mesogens. Angew Chem Int Ed. 2015;54:4110–4114.
  • Lehmann M, Maier P. Shape-persistent, sterically crowded star mesogens: from exceptional columnar dimer stacks to supermesogens. Angew Chem Int Ed. 2015;54:9710–9714.
  • Wöhrle T, Baro A, Laschat S. Novel discotic boroxines: synthesis and mesomorphic properties. Materials. 2014;7:4045–4056.
  • Wöhrle T, Beardsworth SJ, Schilling C, et al. Columnar propeller-like 1,3,5-triphenylbenzenes: the missing link of shape-persistent hekates. Soft Matter. 2016;12:3730–3736.
  • Brock CP, Minton RP, Niedenzu K. Structure and thermal motion of triphenylboroxin. Acta Crystallogr C. 1987;43:1775–1779.
  • Lin YC, Williams DE. 1,3,5-triphenylbenzene. Acta Crystallogr B. 1975;31:318–320.
  • Bastiansen O, Sjöblom L, Motzfeldt K, et al. Deviation from coplanarity in the 1,3,5-triphenylbenzene molecule. Acta Chem Scand. 1952;6:205–213.
  • Damiani A, Giglio E, Ripamonti A. Crystal and molecular structure of s -triphenyltriazine. Acta Crystallogr. 1965;19:161–168.
  • Lee H, Kim D, Lee H-K, et al. Discotic liquid crystalline materials for potential nonlinear optical applications: synthesis and liquid crystalline behavior of 1,3,5-triphenyl-2,4,6-triazine derivatives containing achiral and chiral alkyl chains at the periphery. Tetrahedron Lett. 2004;45:1019–1022.
  • Dierking I. Textures of liquid crystals. Weinheim: Wiley-VCH; 2006.
  • Goodby JW, Collings PJ, Kato T, et al., editors. Handbook of liquid crystals. 2., completely rev. and greatly enlarged ed. Weinheim: Wiley-VCH; 2014.
  • Zucchi G, Donnio B, Geerts YH. Remarkable miscibility between disk- and lathlike mesogens. Chem Mater. 2005;17:4273–4277.
  • Prasad SK, Rao DSS, Chandrasekhar S, et al. X-RAY studies on the columnar structures of discotic liquid crystals. Mol Cryst Liq Cryst. 2003;396:121–139.
  • Fontes E, Heiney PA, de Jeu WH. Liquid-crystalline and helical order in a discotic mesophase. Phys Rev Lett. 1988;61:1202–1205.
  • Demenev A, Eichhorn SH, Taerum T, et al. Quasi temperature independent electron mobility in hexagonal columnar mesophases of an H-bonded benzotristhiophene derivative. Chem Mater. 2010;22:1420–1428.
  • Arikainen EO, Boden N, Bushby RJ, et al. Complimentary polytopic interactions. Angew Chem Int Ed. 2000;39:2333–2336.
  • Pisula W, Kastler M, Wasserfallen D, et al. Pronounced supramolecular order in discotic donor–acceptor mixtures. Angew Chem Int Ed. 2006;45:819–823.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.