The synthesis of [1,2,3]-triazole-based bent core liquid crystals via microwave-mediated ‘Click Reaction’ and their mesomorphic behaviour

References

• Niori T, Sekine T, Watanabe J, et al. Distinct ferroelectric smectic liquid crystals consisting of banana shaped achiral molecules. J Mater Chem. 1996;6(7):1231–1233.
   Web of Science ®Google Scholar
• Jákli A, Chien LC, Krüerke D, et al. Light shutters from antiferroelectric liquid crystals of bent-shaped molecules. Liq Cryst. 2002;29(3):377–381.
   Web of Science ®Google Scholar
• Etxebarria J, Ros MB. Bent-core liquid crystals in the route to functional materials. J Mater Chem. 2008;18(25):2919–2926.
   Web of Science ®Google Scholar
• Kentischer F, Macdonald R, Warnik P, et al. Second harmonic generation (SHG) investigations of different phases of banana shaped molecules. Liq Cryst. 1998;25(3):341–347.
   Web of Science ®Google Scholar
• Seed AJ, Hird M, Styring P, et al. Heterocyclic esters exhibiting frustrated liquid crystal phases. Mol Cryst Liq Cryst. 1997;299:19–25.
   Web of Science ®Google Scholar
• Han J. 1,3,4-Oxadiazole based liquid crystals. J Mater Chem C. 2013;1(47):7779–7797.
   Web of Science ®Google Scholar
• Apreutesi D, Mehl G. The design and investigation of laterally functionalized oxadiazoles. J Mater Chem. 2007;17(44):4711–4715.
   Web of Science ®Google Scholar
• Shanker G, Prehm M, Nagaraj M, et al. 1,2,4-Oxadiazole-based bent-core liquid crystals with cybotactic nematic phases. Chem Phys Chem. 2014;15(7):1323–1335.
   Web of Science ®Google Scholar
• Han J, Chang XY, Wang YM, et al. Synthesis, crystal structures, mesomorphic and photo-luminescent properties of 1,3,4-thia(oxa)diazole-based compounds with a terminal methoxy or methylthio group. J Mol Struct. 2009;937(1–3):122–130.
   Web of Science ®Google Scholar
• Tuzimoto P, Santos DMPO, Moreira T, et al. Luminescent liquid crystals containing a sulphur-based heterocyclic core. Liq Cryst. 2014;41(8):10971108.
   Web of Science ®Google Scholar
• Iglesias R, Serrano JL, Sierra T. FLCs with a five-membered ring in the mesogenic core. Liq Cryst. 1997;22(1):37–46.
   Web of Science ®Google Scholar
• Hariprasad S, Srinivasa HT. Symmetric 3,5-pyrazole and isoxazole heterocycles comprising a bent core unit: synthesis and mesomorphic characterisation. Liq Cryst. 2015;42(11):1612–1620.
   Web of Science ®Google Scholar
• Conte G, Ely F and Gallardo H. An investigation of the synthesis of chiral LCs based on the [1,2,3]-triazole ring. Liq Cryst. 2005;32(10):1213–1222.
   Web of Science ®Google Scholar
• Gallardo H, Ely F, Bortoluzzi AJ, et al. Applying click chemistry to synthesis of chiral [1,2,3]-triazole liquid. Crystals Liq Cryst. 2005;32(6):667–671.
   Web of Science ®Google Scholar
• Cheng HM, Ma C, Chen Y, et al. Monosubstituted ferrocene liquid crystals containing click triazole with a wide nematic phase temperature range. Liq Cryst. 2017;44(9):1450–1461.
   Web of Science ®Google Scholar
• Ovalle S, Westphal E, Gallardo H. Ionic liquid crystals with 1,2,3-triazole + tolane core and a pendant imidazolium unit: mesophases from one- to three-dimensional molecular organisation by the variation of alkoxy chains number and spacer length. Liq Cryst. 2018;45(6):942–952.
   Web of Science ®Google Scholar
• Silva L, Gallardo H, Magnago RF, et al. Liquid crystals containing the isoxazole and tetrazole heterocycles. Mol Cryst Liq Cryst. 2005;432(1):1–13.
   Web of Science ®Google Scholar
• Takezoe H, Takanishi Y. Bent-core liquid crystals: their mysterious and attractive world. Jpn J Appl Phys. 2006;45(2A):597–625.
   Web of Science ®Google Scholar
• Viney C, Brown DJ, Dannels CM, et al. High strength disclinations in a rigid rod nematic polytolane. Liq Cryst. 1993;13(1):95–100.
   Web of Science ®Google Scholar
• Castellano JA. Liquid gold: the story of liquid crystal displays and the creation of an industry. Singapore: World Scientific Publishing; 2005.
   Google Scholar
• Peng F, Chen Y, Wu ST, et al. Low loss liquid crystals for infrared applications. Liq Cryst. 2014;41(11):1445–1552.
   Web of Science ®Google Scholar
• Szilvási T, Roling LT, Yu H, et al. Design of chemoresponsive liquid crystals through integration of computational chemistry and experimental studies. Chem Mater. 2017;29:2563–3571.
   Web of Science ®Google Scholar
• Rostovtsev VV, Green LG, Fokin VV, et al. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew Chem Int Ed. 2002;41(14):2596–2599.
   PubMed Web of Science ®Google Scholar
• Thevenet D, Neier R. Click chemistry applied in the synthesis of symmetrical triphenylene-based discotic liquid-crystalline dimers. Synthesis. 2011;2011(23):3801–3806.
   Web of Science ®Google Scholar
• Li YJ, Flood AH. Strong, size-selective, and electronically tunable C-H···halide binding with steric control over aggregation from synthetically modular, shape-persistent [34]triazolophanes. J Am Chem Soc. 2008;130(36):12111–12122.
   PubMed Web of Science ®Google Scholar
• Chandrudu S, Simerska P, Toth I. Chemical methods for peptide and protein production. Molecules. 2013;18:4373–4388.
   PubMed Web of Science ®Google Scholar
• Patil S, White K, Bugarin A. Novel triazene dyes from N-heterocyclic carbenes and azides: syntheses, stability, and spectroscopic properties. Tetrahedron Lett. 2014;55(34):4826–4829.
   Web of Science ®Google Scholar
• Talati JD, Gandhi DK. N-heterocyclic compounds as corrosion inhibitors for aluminum-copper alloy in hydrochloric acid. Corros Sci. 1983;23(12):1315–1332.
   Web of Science ®Google Scholar
• Scott G, editor. Developments in polymer stabilisation—8. Netherlands: Springer; 2012.
   Google Scholar
• Krygowski TM, Cyranski MK, editors. Aromaticity in heterocyclic compounds. Berlin Heidelberg: Springer-Verlag; 2009.
   Google Scholar
• Conte G, Cristiano R, Ely F, et al. New 1,4-diaryl [1,2,3]-triazole liquid crystals using a Click Reaction. Syn Commun. 2006;36(7):951–958.
   Web of Science ®Google Scholar
• Gallardo H, Bortoluzzi AJ, De Oliveira Santos DMP. Synthesis, crystalline structure and mesomorphic properties of new liquid crystalline 1,2,3-triazole derivatives. Liq Cryst. 2008;35(6):719–725.
   Web of Science ®Google Scholar
• Girotto E, Bechtold IH, Gallardo H. New liquid crystals derived from thiophene connected to the 1,2,3-triazole heterocycle. Liq Cryst. 2015;42(12):1798–1807.
   Web of Science ®Google Scholar
• Benbayer C, Saidi-Besbes S, Grelet E, et al. Structure-property study of new [1,2,3]-triazole liquid crystalline derivatives. Liq Cryst. 2013;40(11):1520–1528.
   Web of Science ®Google Scholar
• Benallou S, Saidi-Besbes S, Grelet E, et al. Synthesis and mesomorphic behaviour of unsymmetrical tetracatenar [1,2,3]-triazole derivatives. Liq Cryst. 2016;43(4):505–516.
   Web of Science ®Google Scholar
• Balamurugan S, Yeap GY, Mahmood WAK. Calamitic liquid crystals of 1,2,3-triazole connected to azobenzene: synthesis, characterization and anisotropic properties. Liq Cryst. 2014;41(6):776–783.
   Web of Science ®Google Scholar
• Yeap GY, Alshargabi A, Mahmood WAK, et al. Synthesis, characterization and molecular organization for induced smectic phase of triazole ring in non-symmetric liquid crystalline dimer. Tetrahedron. 2015;71(23):3939–3945.
   Web of Science ®Google Scholar
• Murata S, Nakatsuji R, Tomioka H. Mechanistic studies of pyrene-sensitized decomposition of p-butylphenyl azide: generation of nitrene radical anion through a sensitizer-mediated electron transfer from amines to the azide. J Chem Soc Perkin Trans 2: Phys Org Chem. 1972–1999. 1995(4):793–800.
   Google Scholar
• Altimari JM, Niranjan B, Risbridger GP, et al. Preliminary investigations into triazole derived androgen receptor antagonists. Bioorg Med Chem. 2014;22(9):2692–2706.
   PubMed Web of Science ®Google Scholar
• Dawson DJ, Frazier JD, Brock PJ, et al. Polymers for high technology. ACS Symp Ser. Chapter 38, Co-cyclotrimerization of aryl acetylenes. substituent effects on reaction rate, 1987;346:445–456.
   Google Scholar
• Keles M, Ylmaz MK. Synthesis, characterization and catalytic activity of new aminomethyldiphosphine-Pd(II) complexes for Suzuki cross-coupling reaction. Appl Organometal Chem. 2014;28(2):91–94.
   Web of Science ®Google Scholar
• Fabbrizzi P, Cicchi S, Brandi A, et al. An efficient (2-aminoarenethiolato)copper(I) complex for the Copper-Catalysed Huisgen Reaction (CuAAC). Eur J Org Chem. 2009;(31):5423–5430.
   Web of Science ®Google Scholar
• Lim H, Chang JY. Preparation of clickable microporous hydrocarbon particles based on adamantane. Macromolecules. 2010;43(17):6943–6945.
   Web of Science ®Google Scholar
• Diez-Gonzalez S, Nolan SP. [(NHC)2Cu]X complexes as efficient catalysts for azide-alkyne click chemistry at low catalyst loadings. Angew Chem Int Ed. 2008;47(46):8881–8884.
   PubMed Web of Science ®Google Scholar
• Hohloch S, Scheiffele D, Sarkar B. Activating azides and alkynes for the Click Reaction with [Cu(aNHC)2I] or [Cu(aNHC)2]+ (aNHC = triazole-derived abnormal carbenes): structural characterization and catalytic properties. Eur J Inorg Chem. 2013;2013(22–23):3956–3965.
   Web of Science ®Google Scholar
• Champagne PA, Desroches J, Paquin JT. Organic fluorine as a hydrogen-bond acceptor: recent examples and applications. Synthesis. 2015;47(3):306–322.
   Web of Science ®Google Scholar
• Patrick CR, Prosser GS. A molecular complex of benzene and hexafluorobenzene. Nat. 1960;187(4742)1021.
   Web of Science ®Google Scholar