Discotic mesogens based on triphenylene-fused benzimidazole or perimidine: facile synthesis, mesomorphism, optical properties and self-assembly

References

• Wöhrle T, Wurzbach I, Kirres J, et al. Discotic liquid crystals. Chem Rev. 2016;116:1139–1241.
   PubMed Web of Science ®Google Scholar
• Kumar Pala S, Setia S, Avinash BS, et al. Triphenylene-based discotic liquid crystals: recent advances. Liq Cryst. 2013;40:1769–1816.
   Web of Science ®Google Scholar
• Osawa T, Kajitani T, Hashizume D, et al. Wide-range 2D lattice correlation unveiled for columnarly assembled triphenylene hexacarboxylic esters. Angew Chem Int Ed. 2012;51:7990–7993.
   PubMed Web of Science ®Google Scholar
• Lee JJ, Yamaguchi A, Alam MA, et al. Discotic ionic liquid crystals of triphenylene as dispersants for orienting single-walled carbon nanotubes. Angew Chem Int Ed. 2012;51:8490–8494.
   PubMed Web of Science ®Google Scholar
• Kumar S. Self-organization of disc-like molecules: chemical aspects. Chem Soc Rev. 2006;35:83–109.
   PubMed Web of Science ®Google Scholar
• 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.
   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.
   PubMed Web of Science ®Google Scholar
• Pérez D, Guitián E. Selected strategies for the synthesis of triphenylenes. Chem Soc Rev. 2004;33:274–283.
   PubMed Web of Science ®Google Scholar
• Gupta RK, Manjuladevi V, Karthik C, et al. Thin films of discotic liquid crystals and their applications. Liq Cryst. 2016;43:2079–2091.
   Web of Science ®Google Scholar
• Buess CM, Lawson DD. The preparation, reactions, and properties of triphenylenes. Chem Rev. 1960;60:313–330.
   Web of Science ®Google Scholar
• Cammidge AN, Chausson C, Gopee H, et al. Probing the structural factors influencing columnar mesophase formation and stability in triphenylene discotics. Chem Commun. 2009;47:7375–7377.
   Web of Science ®Google Scholar
• Cammidge AN. The effect of size and shape variation in discotic liquid crystals based on triphenylene cores. Philos Trans R Soc London Ser A. 2006;364:2697–2708.
   PubMed Web of Science ®Google Scholar
• Cammidge AN, Gopee H. Structural factors controlling the transition between columnar-hexagonal and helical mesophase in triphenylene liquid crystals. J Mater Chem. 2001;11:2773–2783.
   Web of Science ®Google Scholar
• Kumar S. Chemistry of discotic liquid crystals: from monomers to polymers. Boca Raton, FL: CRC Press; 2011.
   Google Scholar
• Kong X, He Z, Zhang Y, et al. A mesogenic triphenylene-perylene-triphenylene triad. Org Lett. 2011;13:764–767.
   PubMed Web of Science ®Google Scholar
• Chen HM, Zhao KQ, Wang L, et al. Synthesis and mesomorphism of triphenylene discotic liquid crystals containing fluorinated chains. Soft Mater. 2011;9:359–381.
   Web of Science ®Google Scholar
• Kaller M, Staffeld P, Haug R, et al. Substituted crown ethers as central units in discotic liquid crystals: effects of crown size and cation uptake. Liq Cryst. 2011;38:531–553.
   Web of Science ®Google Scholar
• Foster EJ, Jones RB, Lavigueur C, et al. Structural factors controlling the self-assembly of columnar liquid crystals. J Am Chem Soc. 2006;128:8569–8574.
   PubMed Web of Science ®Google Scholar
• Pisula W, Tomovic Z, Simpson C, et al. Relationship between core size, side chain length, and the supramolecular organization of polycyclic aromatic hydrocarbons. Chem Mater. 2005;17:4296–4303.
   Web of Science ®Google Scholar
• Lau K, Foster J, Williams V. Synthesis of a hexaalkoxybenzo[b]triphenylene mesogen. Chem Commun. 2003;17:2172–2173.
   Web of Science ®Google Scholar
• Van de Craats AM, Warman JM. The core-size effect on the mobility of charge in discotic liquid crystalline materials. Adv Mater. 2001;13:130–133.
   Web of Science ®Google Scholar
• Yatabe T, Harbison MA, Brand JD, et al. Extended triphenylenes: synthesis, mesomorphic properties and molecularly resolved scanning tunneling microscopy images of hexakis(dialkoxyphenyl) triphenylenes and dodeca(alkoxy)tris(triphenylenylene)s. J Mater Chem. 2000;10:1519–1525.
   Web of Science ®Google Scholar
• Feng HY, Geng XT, Lin JR, et al. Novel fluorescent liquid crystals: synthesis, mesomorphism and fluorescence of triphenylene-bodipy derivatives based on 1,3,5-triazine core. Liq Cryst. 2018;45:1470–1476.
   Web of Science ®Google Scholar
• Litterscheidt J, Judge P, Buhlmeyer A, et al. triphenylene-derived ionic liquid crystals in comparison with guanidinium and ammonium units. Liq Cryst. 2018;45:1250–1258.
   Web of Science ®Google Scholar
• Sahamir SR, Said SM, Sabri MFM, et al. Studies on relation between columnar order and electrical conductivity in HAT6 discotic liquid crystals using temperature-dependent Raman spectroscopy and DFT calculations. Liq Cryst. 2018;45:522–535.
   Web of Science ®Google Scholar
• Voisin E, Johan Foster E, Rakotomalala M, et al. Effects of symmetry on the stability of columnar liquid crystals. Chem Mater. 2009;21:3251–3261.
   Web of Science ®Google Scholar
• Lavigueur C, Foster EJ, Williams VE. Self-assembly of discotic mesogens in solution and in liquid crystalline phases: effects of substituent position and hydrogen bonding. J Am Chem Soc. 2008;130:11791–11800.
   PubMed Web of Science ®Google Scholar
• Kumar S. Recent developments in the chemistry of triphenylene-based discotic liquid crystals. Liq Cryst. 2004;31:1037–1059.
   Web of Science ®Google Scholar
• Cammidge AN, Gopee H. Macrodiscotic triphenylenophthalocyanines. Chem Commun. 2002:966–967.
   PubMed Web of Science ®Google Scholar
• Cammidge AN, Bushby RJ. Handbook of liquid crystals. Demus D, Goodby J, GW G, et al., editors. Vol. 2B. New York: Wiley-VCH; 1998. p. 693.
   Google Scholar
• Paraschiv I, Giesbers M, van Lagen B, et al. H-bond-stabilized triphenylene-based columnar discotic liquid crystals. Chem Mater. 2006;18:968–974.
   Web of Science ®Google Scholar
• Feng C, Ding YH, Han XD, et al. Triphenylene 2, 3-dicarboxylic imides as luminescent liquid crystals: mesomorphism, optical and electronic properties. Dyes Pigm. 2017;139:87–96.
   Web of Science ®Google Scholar
• Feng X, Marcon V, Pisula W, et al. Towards high charge-carrier mobilities by rational design of the shape and periphery of discotics. Nat Mater. 2009;8:421–426.
   PubMed Web of Science ®Google Scholar
• Kumar S, Gupta SK. Novel triphenylenoimidazole discotic liquid crystals. Tetrahedron Lett. 2011;52:5363–5367.
   Web of Science ®Google Scholar
• Fleischmann E, Zentel R. Liquid-crystalline ordering as a concept in materials science: from semiconductors to stimuli-responsive devices. Angew Chem Int Ed. 2013;52:8810–8827.
   PubMed Web of Science ®Google Scholar
• Yeh P, Gu C. Optics of liquid crystal displays. Hoboken, NJ: Willey; 2010.
   Google Scholar
• Lau K, Foster J, Williams V. Synthesis of a hexaalkoxybenzo[b]triphenylene mesogen. Chem Commun. 2003:2172–2173.
   PubMed Web of Science ®Google Scholar
• Kumar S, Varshney SK. Dibenzo[g,p]chrysene, a novel core for discotic liquid crystals. Mol Cryst Liq Cryst. 2002;378:59–64.
   Web of Science ®Google Scholar
• Kumar S, Naidu JJ, Shankar Rao DS. Novel dibenzo[fg,op]naphthacene discotic liquid crystals: a versatile rational synthesis. J Mater Chem. 2002;12:1335–1341.
   Web of Science ®Google Scholar
• Carmen Artal C, Toyne KJ, Goodby JW, et al. Synthesis and mesogenic properties of novel board-like liquid crystals. J Mater Chem. 2001;11:2801–2807.
   Web of Science ®Google Scholar
• Ito S, Wehmeier M, Diedrich Brand J, et al. Synthesis and self-assembly of functionalized hexa-peri-hexabenzocoronenes. Chemistry. 2000;6:4327–4342.
   PubMed Web of Science ®Google Scholar
• Boden N, Bushby RJ, Headdock G, et al. Syntheses of new ‘large core’ discogens based on the triphenylene, azatriphenylene and hexabenztrinaphthylene nuclei. Liq Cryst. 2001;28:139–144.
   Web of Science ®Google Scholar
• Li J, Zhang Q. Linearly fused azaacenes: novel approaches and new applications beyond field-effect transistors (fets). ACS Appl Mater Interfaces. 2015;7:28049–28062.
   PubMed Web of Science ®Google Scholar
• Bunz UHF. The larger linear N-heteroacenes. Acc Chem Res. 2015;48:1676–1686.
   PubMed Web of Science ®Google Scholar
• Stępien M, Gońka E, Żyła M, et al. Heterocyclic nanographenes and other polycyclic heteroaromatic compounds: synthetic routes, properties, and applications. Chem Rev. 2017;117:3479–3716.
   PubMed Web of Science ®Google Scholar
• Yin J, Qu HM, Zhang K, et al. Electron-deficient triphenylene and trinaphthylene carboximides. Org Lett. 2009;11:3028–3031.
   PubMed Web of Science ®Google Scholar
• Psutka KM, Bozek KJ, Maly KE. Synthesis and mesomorphic properties of novel dibenz[a,c]anthracenedicarboximides. Org Lett. 2014;16:5442–5445.
   PubMed Web of Science ®Google Scholar
• Xiao WK, He ZQ, Remiro-Buenamañana S, et al. A π-extended donor-acceptor-donor triphenylene twin linked via a pyrazine bridge. Org Lett. 2015;17:3286–3289.
   PubMed Web of Science ®Google Scholar
• Zhao B, Liu B, Png RQ, et al. New discotic mesogens based on triphenylene-fused triazatruxenes: synthesis, physical properties, and self-assembly. Chem Mater. 2010;22:435–449.
   Web of Science ®Google Scholar
• Kumar S, Manickam M. Synthesis of phenanthro[a]phenazine derivatives: a novel ring structure forming discotic liquid crystals. Liq Cryst. 1999;26:1097–1099.
   Web of Science ®Google Scholar
• Kumar S, Manickam M. Synthesis of phenanthro[b] phenazine, a novel heterocyclic ring structure for discotic liquid crystals. Mol Cryst Liq Cryst. 2000;338:175–179.
   Web of Science ®Google Scholar
• Gowda A, Jacob L, Patra A, et al. Synthesis, mesomorphic properties and nonlinear optical studies of alkyl and alkoxyphenylacetylene containing phenazine fused extended triphenylene discotic liquid crystalline dyes. Dyes Pigm. 2019;160:128–135.
   Web of Science ®Google Scholar
• Mamada M, Perez-Bolivar C, Kumaki D, et al. Benzimidazole derivatives: synthesis, physical properties, and n-type semiconducting properties. Chem Eur J. 2014;20:11835–11846.
   PubMed Web of Science ®Google Scholar
• Perrin L, Hudhomme P. Synthesis, electrochemical and optical absorption properties of new perylene-3,4:9,10-bis(dicarboximide) and perylene-3,4:9,10-bis(benzimidazole) derivatives. Eur J Org Chem. 2011;2011:5427–5440.
   Web of Science ®Google Scholar
• Mizuguchi J. Crystal structure and electronic characterization of trans- and cis-perinone pigments. J Phys Chem B. 2004;108:8926–8930.
   Web of Science ®Google Scholar
• Tam-Chang SW, Seo W, Rove K, et al. Molecularly designed chromonic liquid crystals for the fabrication of broad spectrum polarizing materials. Chem Mater. 2004;16:1832–1834.
   Web of Science ®Google Scholar
• Zhang Y, Hanifi D, Alvarez S, et al. Charge transport anisotropy in n-type disk-shaped triphenylene-tris(aroyleneimidazole)s. Org Lett. 2011;13:6528–6531.
   PubMed Web of Science ®Google Scholar
• Feng C, Tian XL, Zhou J, et al. A convenient tandem one-pot synthesis of donor-acceptor-type triphenylene 2,3-dicarboxylic esters from diarylacetylene. Org Biomol Chem. 2014;12:6977–6981.
   PubMed Web of Science ®Google Scholar
• Han XD, Tian XL, Yu WH, et al. Influence of peripheral alkyl chain length on the mesomorphic behaviours of hexasubstituted triphenylene 2,3-dicarboxylic esters. Liq Cryst. 2017;44:1727–1738.
   Web of Science ®Google Scholar
• Diana P, Martorana A, Barraja P, et al. Isoindolo[2,1-c]benzo[1,2,4]triazines:anew ring system with antiproliferative activity. Bioorg Med Chem. 2007;15:343–349.
   PubMed Web of Science ®Google Scholar
• Herbst W, Hunger K. Industrial organic pigments. 3rd ed. Weinheim: Wiley-VCH; 2004. p. 9–11.
   Google Scholar
• Yamato K, Sekiya R, Suzuki K, et al. Near-infrared-emitting nitrogen-doped nanographenes. Angew Chem Int Ed. 2019;58:1–6.
   Web of Science ®Google Scholar
• Fernandez-Garcia JM, Evans PJ, Medina Rivero S, et al. π-extended corannulene-based nanographenes: selective formation of negative curvature. J Am Chem Soc. 2018;140:17188–17196.
   PubMed Web of Science ®Google Scholar
• Camerel F, Ziessel R, Donnio B, et al. Formation of gels and liquid crystals induced by Pt-Pt and π-π* interactions in luminescent σ-alkynyl platinum(ii) terpyridine complexes. Angew Chem Int Ed. 2007;46:2659–2662.
   PubMed Web of Science ®Google Scholar
• Babu SS, Praveen VK, Kartha KK, et al. Effect of the bulkiness of the end functional amide groups on the optical, gelation, and morphological properties of oligo(p-phenylenevinylene) π-gelators. Chem-Asian J. 2014;9:1830–1840.
   PubMed Web of Science ®Google Scholar
• Yoshida R. Self-oscillating gels driven by the belousov-zhabotinsky reaction as novel smart materials. Adv Mater. 2010;22:3463–3483.
   PubMed Web of Science ®Google Scholar