A modified route to unsymmetrically substituted triphenylenes, new functionalised derivatives and twins, and the smallest reported triphenylene mesogen

References

• Cammidge AN, Bushby RJ. Discotic liquid crystals: synthesis and structural features. In: Demus D, Goodby JW, Gray GW, et al., editors. Handbook of liquid crystals Vol. 2. Weinheim: Wiley-VCH; 1998. p. 693–748.
   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
• Kumar S. Chemistry of discotic liquid crystals. Florida: CRC Press; 2010.
   Google Scholar
• Pal SK, Setia S, Avinash BS, et al. Triphenylene-based discotic liquid crystals: recent advances. Liq Cryst. 2013;40:1769–1816.
   Web of Science ®Google Scholar
• Setia S, Sidiq S, De J, et al. Applications of liquid crystals in biosensing and organic light-emitting devices: future aspects. Liq Cryst. 2016;43:2009–2050.
   Web of Science ®Google Scholar
• Wöhrle T, Wurzbach I, Kirres J, et al. Discotic liquid crystals. Chem Rev. 2016;116:1139–1241.
   PubMed Web of Science ®Google Scholar
• Cammidge AN. The effect of size and shape variation in discotic liquid crystals based on triphenylene cores. Phil Trans R Soc A. 2006;364:2697–2708.
   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
• Cammidge AN, Chausson C, Gopee H, et al. Probing the structural factors influencing columnar mesophase formation and stability in triphenylene discotics. Chem Commun. 2009;7375–7377.
   PubMed Web of Science ®Google Scholar
• Cammidge AN, Gopee H. Mixed alkyl-alkoxy triphenylenes. Mol Cryst Liq Cryst. 2003;397:117–128.
   Web of Science ®Google Scholar
• Cammidge AN, Gopee H. Synthesis and liquid crystal properties of mixed alkynyl-alkoxy-triphenylenes. Liq Cryst. 2009;36:809–816.
   Web of Science ®Google Scholar
• Zhang L, Gopee H, Hughes DL, et al. Antiaromatic twinned triphenylene discotics showing nematic phases and 2-dimensional -overlap in the solid state. Chem Commun. 2010;46:4255–4257. DOI:10.1039/c0cc00311e
   PubMed Web of Science ®Google Scholar
• Zhang L, Hughes DL, Cammidge AN. Discotic triphenylene twins linked through thiophene bridges: controlling nematic behavior in an intriguing class of functional organic materials. J Org Chem. 2012;77:4288–4297.
   PubMed Web of Science ®Google Scholar
• Gopee H, Kong X, He Z, et al. Expanded porphyrin-like structures based on twinned triphenylenes. J Org Chem. 2013;78:9505–9511.
   PubMed Web of Science ®Google Scholar
• Cammidge AN, Obi G, Turner RJ, et al. The synthesis of unsymmetrically substituted triphenylenes through controlled construction of the core and subsequent aromatic substitution reactions – a perspective and update. Liq Cryst. 2015;42:819–825.
   Web of Science ®Google Scholar
• Cammidge AN, Gopee H. Design and synthesis of nematic phases formed by disk-like molecules. In: Goodby JW, Collings PJ, Kato T, et al., editors. Handbook of Liquid Crystals. Vol. 3. 2nd ed. Weinheim: Wiley-VCH; 2014. p. 293–334.
   Google Scholar
• Cammidge AN, Gopee H. Macrodiscotic triphenylenophthalocyanines. Chem Commun. 2002;966–967.
   PubMed Web of Science ®Google Scholar
• Xiao WK, He ZQ, Remiro-Buenamañana S, et al. A -extended donor-acceptor-donor triphenylene twin linked via a pyrazine bridge. Org Lett. 2015;17:3286–3289.
   PubMed Web of Science ®Google Scholar
• Kong X, He Z, Zhang YN, et al. A mesogenic triphenylene-perylene-triphenylene triad. Org Lett. 2015;13:764–767.
   Web of Science ®Google Scholar
• Goodby JW, Hird M, Toyne KJ, et al. A novel, efficient and general synthetic route to unsymmetrical triphenylene mesogens using palladium-catalysed cross-coupling reactions. J Chem Soc Chem Commun. 1994;1701–1702.
   Google Scholar
• Boden N, Bushby RJ, Cammidge AN. A quick-and-easy route to unsymmetrically substituted derivatives of triphenylene: preparation of polymeric discotic liquid crystals. J Chem Soc Chem Commun. 1994;465–466.
   Google Scholar
• Boden N, Bushby RJ, Cammidge AN. Triphenylene-based discotic-liquid-crystalline polymers: a universal rational synthesis. J Am Chem Soc. 1995;117:924–927.
   Web of Science ®Google Scholar
• Astruc D. Why is ferrocene so exceptional? Eur J Inorg Chem. 2017;6–29.
   Web of Science ®Google Scholar
• Loudet A, Burgess K. BODIPY dyes and their derivatives: syntheses and spectroscopic properties. Chem Rev. 2007;107:4891–4932.
   PubMed Web of Science ®Google Scholar
• Dutta T, Che Y, Zhong H, et al. Synthesis and self-assembly of triphenylene-containing conjugated macrocycles. RSC Adv. 2013;3:6008–6015.
   Web of Science ®Google Scholar