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Research Article

C3-symmetric truxene discotic liquid crystals with mixed ether chains: synthesis, mesomorphism, and self-assembly properties

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Pages 394-404 | Received 11 Feb 2022, Accepted 11 Mar 2022, Published online: 21 Mar 2022

References

  • Laschat, S.; Baro, A.; Steinke, N.; Giesselmann, F.; Hagele, C.; Scalia, G.; Judele, R.; Kapatsina, E.; Sauer, S.; Schreivogel, A., et al. Discotic Liquid Crystals: From Tailor-made Synthesis to Plastic Electronics. Angew Chem. Int. Ed. 2007, 46, 4832–4887. DOI: 10.1002/anie.200604203.
  • Sergeyev, S.; Pisula, W.; Geerts, Y. H. Discotic Liquid Crystals: A New Generation of Organic Semiconductors. Chem. Soc. Rev. 2007, 36, 1902–1929. DOI: 10.1039/b417320c.
  • Kaafarani, B. R. Discotic Liquid Crystals for Opto-Electronic Applications. Chem. Mater. 2011, 23, 378–396. DOI: 10.1021/cm102117c.
  • Wohrle, T.; Wurzbach, I.; Kirres, J.; Kostidou, A.; Kapernaum, N.; Litterscheidt, J.; Haenle, J. C.; Staffeld, P.; Baro, A.; Giesselmann, F., et al. Discotic Liquid Crystals. Chem. Rev. 2016, 116, 1139–1241. DOI: 10.1021/acs.chemrev.5b00190.
  • Bushby, R. J.; Lozman, O. R. Discotic Liquid Crystals 25 Years On. Curr. Opin. Colloid Interface Sci. 2002, 7, 343–354. DOI: 10.1016/S1359-0294(02)00085-7.
  • Kumar, S. Playing with Discs. Liq. Cryst. 2009, 36, 607–638. DOI: 10.1080/02678290902755549.
  • Kato, T.; Uchida, J.; Ichikawa, T.; Sakamoto, T. Functional Liquid Crystals Towards the Next Generation of Materials. Angew Chem. Int. Ed. 2018, 57, 4355–4371. DOI: 10.1002/anie.201711163.
  • Shi, K.; Wang, J. Y.; Pei, J. π-Conjugated Aromatics Based on Truxene: Synthesis, Self-Assembly, and Applications. Chem. Rec. 2015, 15, 52–72. DOI: 10.1002/tcr.201402071.
  • Goubard, F.; Dumur, F. Truxene: A Promising Scaffold for Future Materials. RSC Adv. 2015, 5, 3521–3551. DOI: 10.1039/C4RA11559G.
  • Bala, I.; Pal, S. K. Rod-disc Oligomeric Liquid Crystal Based on 4-cyanobiphenyl and Truxene Core. Liq. Cryst. 2016, 43, 963–971. DOI: 10.1080/02678292.2016.1153733.
  • Zhao, B. M.; Liu, B.; Png, R. Q.; Zhang, K.; Lim, K. A.; Luo, J.; Shao, J. J.; Ho, P. K. H.; Chi, C. Y.; Wu, J. S. New Discotic Mesogens Based on Triphenylene-Fused Triazatruxenes: Synthesis, Physical Properties, and Self-Assembly. Chem. Mater. 2009, 22, 435–449. DOI: 10.1021/cm903555s.
  • Destrade, C.; Gasparoux, H.; Babeau, A.; Tinh, N. H.; Malthete, J. Truxene Derivatives: A New Family of Disk-like Liquid Qrystals with an Inverted Nematic-columnar Sequence. Mol. Cryst. Liq. Cryst. 1981, 67, 37–47. DOI: 10.1080/00268948108070873.
  • Tinh, N. H.; Foucher, P.; Destrade, C.; Levelut, A. M.; Malthete, J. Reentrant Mesophases in Disk-like Liquid Crystals. Mol. Cryst. Liq. Cryst. 1984, 111, 277–292. DOI: 10.1080/00268948408072438.
  • Buisine, J. M.; Cayuela, R.; Destrade, C.; Tinh, N. H. Dilatometric and Thermobarometric Measurements of Truxene Derivatives Exhibiting Inverted and Reentrant Sequences. Mol. Cryst. Liq. Cryst. 1987, 144, 137–160. DOI: 10.1080/15421408708084210.
  • Warmerdam, T. W.; Nolte, R. J. M.; Drenth, W.; Van Miltenburg, J. C.; Frenkel, D.; Zijlstra, R. J. J. Discotic Liquid Crystals Physical Parameters of Some 2,3,7,8,12,13-hexa(alkanoyloxy)truxenes: Observation of a Reentrant Isotropic Phase in a Pure Disk-like Mesogen. Liq. Cryst. 1988, 3, 1087–1104. DOI: 10.1080/02678298808086564.
  • Warmerdam, T. W.; Frenkel, D.; Zijlstra, R. J. J. Dynamics of the Frederiks Transition in Nematics Consisting of Disk-like Molecules. Thermal Dependence of a Bend Viscosity Coefficient. Liq. Cryst. 1988, 3, 1105–1114. DOI: 10.1080/02678298808086565.
  • Lee, W. K.; Wintner, B. A.; Fontes, E.; Heiney, P. A.; Ohba, M.; Haseltine, J. N.; Smith, A. B. Reentrant Isotropic Phase in a Discotic Liquid Crystal Mixture. Liq. Cryst. 1989, 4, 87–102. DOI: 10.1080/02678298908028961.
  • Lee, W. K.; Heiney, P. A.; Ohba, M.; Haseltine, J. N.; Smith, A. B. Fourier Transform Infrared Study of Two Truxene-based Discotic Liquid Crystals. Liq. Cryst. 1990, 8, 839–850. DOI: 10.1080/02678299008047394.
  • Perova, T. S.; Vij, J. K.; Bock, H. IR Spectroscopic Study of the Electric Field Induced Phase Transition of a Ferroelectrically Switchable Columnar Dibenzopyrene. Mol. Cryst. Liq. Cryst. 1995, 263, 2225–2235. DOI: 10.1080/10587259508033593.
  • Sandstroem, D.; Nygren, M.; Zimmermann, H.; Maliniak, A. Deuterium NMR Investigation of a Discotic Mesogen Based on Hexasubstituted Truxene. J. Phys. Chem. 1995, 99, 6661–6669. DOI: 10.1021/j100017a057.
  • Dvinskikh, S. V.; Furó, I.; Zimmermann, H.; Maliniak, A. Molecular Self-diffusion in a Columnar Liquid Crystalline Phase Determined by Deuterium NMR. Phys. Rev. E. 2002, 65, 050702. DOI: 10.1103/PhysRevE.65.050702.
  • Negita, K.; Kawano, C.; Moriya, K. Rheological Properties in Discotic Liquid Crystalline Phases of 2,3,7,8,12,13-hexa(n-tetradecanoyloxy)truxene. Phys. Rev. E. 2004, 70, 021702. DOI: 10.1103/PhysRevE.70.021702.
  • Isoda, K.; Yasuda, T.; Kato, T. Truxene-Based Columnar Liquid Crystals: Self-Assembled Structures and Electro-Active Properties. Chem. Asian J. 2009, 4, 1619–1625. DOI: 10.1002/asia.200900038.
  • Vinayakumara, D. R.; Kumar, M.; Sreekanth, P.; Philip, R.; Kumar, S. Synthesis, Characterization and Nonlinear Optical Studies of Novel Blue-light Emitting Room Temperature Truxene Discotic Liquid Crystals. RSC Adv. 2015, 5, 26596–26603. DOI: 10.1039/C5RA00873E.
  • Zhao, K. Q.; Chen, C.; Monobe, H.; Hu, P.; Wang, B. Q.; Shimizu, Y. Three-chain Truxene Discotic Liquid Crystal Showing High Charged Carrier Mobility. Chem. Commun. 2011, 47, 6290–6292. DOI: 10.1039/C1CC10299K.
  • Ni, H. L.; Monobe, H.; Hu, P.; Wang, B. Q.; Shimizu, Y.; Zhao, K. Q. Truxene Discotic Liquid Crystals with Two Different Ring Substituents: Synthesis, Mesomorphism and High Charged Carrier Mobility. Liq. Cryst. 2013, 40, 411–420. DOI: 10.1080/02678292.2012.755224.
  • Monobe, H.; Ni, H. L.; Hu, P.; Wang, B. Q.; Zhao, K. Q.; Shimizu, Y. Carrier Transport Property of Truxene Discotic Liquid Crystals with Three Different Ring Substituents. Jpn. J. Appl. Phys. 2016, 55, 03DE01. DOI: 10.7567/jjap.55.03de01.
  • Wang, J. Y.; Yan, J.; Li, Z.; Han, J. M.; Ma, Y.; Bian, J.; Pei, J. Isomeric Effect on Microscale Self-Assembly: Interplay between Molecular Property and Solvent Polarity in the Formation of 1D n-Type Microbelts. Chem. Eur. J. 2008, 14, 7760–7764. DOI: 10.1002/chem.200800396.
  • Wang, J. Y.; Yan, J.; Ding, L.; Ma, Y.; Pei, J. One-Dimensional Microwires Formed by the Co-Assembly of Complementary Aromatic Donors and Acceptors. Adv. Funct. Mater. 2009, 19, 1746–1752. DOI: 10.1002/adfm.200900093.
  • Li, L. L.; Hu, P.; Wang, B. Q.; Yu, W. H.; Shimizu, Y.; Zhao, K. Q. Synthesis and Mesomorphism of Ether–ester Mixed Tail C3-symmetrical Truxene Discotic Liquid Crystals. Liq. Cryst. 2010, 37, 499–506. DOI: 10.1080/02678290903215337.
  • Ruan, P.; Xiao, B.; Ni, H. L.; Hu, P.; Wang, B. Q.; Zhao, K. Q.; Zeng, Q. D.; Wang, C. The Influence of Alkyl Chain Substitution Pattern on the Two- and Three-dimensional Self-assembly of Truxenone Discogens. Liq. Cryst. 2014, 41, 1152–1161. DOI: 10.1080/02678292.2014.909538.
  • Xu, H. T.; Xia, X.; Yu, W. H.; Feng, C.; Xiang, S. K.; Wang, B. Q.; Zhao, K. Q.; Ni, H. L.; Hu, P. Effect of Methoxy Groups on Liquid Crystalline and Self-assembling Properties of 2,7,12-tris(methoxy)-3,8,13-tris(alkoxy)-5,10,15-truxenones. Liq. Cryst. 2021, 48, 111–120. DOI: 10.1080/02678292.2020.1766136.
  • Foucher, P.; Destrade, C.; Tinh, N. H.; Melthete, J.; Levelut, A. M. Hexaalkoxytruxenes, A New Series of Disc-Like Mesogens. Mol. Cryst. Liq. Cryst. 1984, 108, 219–229. DOI: 10.1080/00268948408078675.
  • Zhang, W.; Yu, W. H.; Feng, C.; Xiang, S. K.; Wang, B. Q.; Zhao, K. Q.; Ni, H. L.; Hu, P. Star-shaped Oligomers with Truxenone Centre and Triphenylene Branches: Mesomorphism, Optical and Electronic Properties. Liq. Cryst. 2020, 47, 1100–1110. DOI: 10.1080/02678292.2019.1706106.
  • Hatsusaka, K.; Ohta, K.; Yamamoto, I.; Shirai, H. Discotic Liquid Crystals of Transition Metal Complexes, Part 30: Spontaneous Uniform Homeotropic Alignment of Octakis(dialkoxyphenoxy)phthalocyaninatocopper(II) Complexes. J. Mater. Chem. 2001, 11, 423–433. DOI: 10.1039/B004406G.
  • Wang, B. Q.; Gao, C. Y.; Zhao, K. Q.; Hu, P. Synthesis and Mesomorphism of Mixed Ether-ester Tail Triphenylene Discotic Liquid Crystals with Long Alkyloxy Peripheral Chains. Front. Chem. 2009, 4, 177–185. DOI: 10.1007/s11458-009-0012-0.
  • Jakli, A. Odd-even Effects in Liquid Crystals. Liq. Cryst. 2022. DOI: 10.1080/02678292.2021.2000054.
  • Hägele, C.; Wuckert, E.; Laschat, S.; Giesselmann, F. Anomalous Odd–Even Effects in Columnar and Smectic Phases of Discotic Tetraphenylenes. ChemPhysChem. 2009, 10, 1291–1298. DOI: 10.1002/cphc.200900090.

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