553
Views
16
CrossRef citations to date
0
Altmetric
Articles

Observation of disordered mesomorphism in three-ring-based highly polar bent-core molecules: design, synthesis and characterisation

ORCID Icon, , , ORCID Icon, ORCID Icon, , ORCID Icon & ORCID Icon show all
Pages 2247-2258 | Received 28 Jun 2017, Accepted 01 Aug 2017, Published online: 18 Aug 2017

References

  • Omaima AE. Bent Core Nematics - Alignment and Electro-Optic Effects [ Ph.D Thesis]. Gothenburg: Department of Physics, University of Gothenburg; 2013.
  • Tadapatri P, Krishnamurthy KS, Weissflog W. Patterned flexoelectric instability in a bent-core nematic liquid crystal. Soft Matter. 2012;8:1202–1214.
  • Niori T, Sekine T, Watanabe J, et al. Distinct ferroelectric smectic liquid crystals consisting of banana shaped achiral molecules. J Mater Chem. 1996;6:1231–1233.
  • Nakata M, Link DR, Thisayukta J, et al. Frustration of polarity and chirality in a binary mixture of bent-core mesogens. J Mater Chem. 2001;11:2694–2699.
  • Thisayukta J, Nakayama Y, Kawauchi S, et al. Distinct formation of a chiral smectic phase in achiral banana-shaped molecules with a central core based on a 2,7-dihydroxynaphthalene unit. J Am Chem Soc. 2000;122:7441–7448.
  • Thisayukta J, Nakayama Y, Kawauchi S, et al. Study on helical structure of the B4 phase formed from achiral banana-shaped molecule. Jpn J Appl Phys. 2001;40:3277–3287.
  • Sekine T, Takanashi Y, Niori T, et al. Ferroelectric properties in banana-shaped achiral liquid crystalline molecular systems. Jpn J Appl Phys. 1997;36:L1201–L1203.
  • Link DR, Natale G, Shao RF, et al. Spontaneous formation of macroscopic chiral domains in a fluid smectic phase of achiral molecules. Science. 1997;278:1924–1927.
  • Coleman DA, Fernsler J, Chattham N, et al. Spontaneous formation of macroscopic chiral domains in a fluid smectic phase of achiral molecules. Science. 2003;301:1204–1211.
  • Reddy RA, Zhu C, Shao RF, et al. Spontaneous ferroelectric order in a bent-core smectic liquid crystal of fluid orthorhombic layers. Science. 2011;332:72–77.
  • Thisayukta J, Niwano H, Takezoe H, et al. Effect of chiral dopant on a helical Sm1 phase of banana-shaped N-n-O-PIMB molecules. J Mater Chem. 2001;11:2717–2721.
  • Araoka F, Park B, Kinoshita Y, et al. Determination of nonlinear hyperpolarizability of bent-shaped molecules using hyper-rayleigh scattering. Mol Cryst Liq Cryst. 1999;328:291–297.
  • Gorecka E, Pociecha D, Araoka F, et al. Ferroelectric phases in a chiral bent-core smectic liquid crystal: dielectric and optical second-harmonic generation measurements. Phys Rev E. 2000;62:R4524–R4527.
  • Takezoe H, Watanabe J. Ferroelectricity in liquid crystals. Mol Cryst Liq Cryst. 1999;328:325–332.
  • MacDonald R, Kentischer F, Warnick P, et al. Antiferroelectricity and chiral order in new liquid crystals of nonchiral molecules studied by optical second harmonic generation. Phy Rev Lett. 1998;81:4408–4411.
  • Kentischer F, MacDonald R, Warnick P, et al. Second harmonic generation (SHG) investigations of different phases of banana shaped molecules. Liq Cryst. 1998;25:341–347.
  • Borshch V, Kim YK, Xiang J, et al. Nematic twist-bend phase with nanoscale modulation of molecular orientation. Nat Commun. 2013;4:2635.
  • Pelzl G, Diele S, Weissflog W. Banana‐shaped compounds—a new field of liquid crystals. Adv Mater. 1999;11:707–724.
  • Tschierske C, Dantlgraber G. From antiferroelectricity to ferroelectricity in smectic mesophases formed by bent-core molecules. Pramana. 2003;61:455–481.
  • Ros MB, Serrano JL, De La Fuente R, et al. Banana-shaped liquid crystals: a new field to explore. J Mater Chem. 2005;15:5093–5098.
  • Reddy RA, Tschierske C. Bent-core liquid crystals: polar order, superstructural chirality and spontaneous desymmetrisation in soft matter systems. J Mater Chem. 2006;16:907–961.
  • Takezoe H, Takanishi Y. Bent-core liquid crystals: their mysterious and attractive world. Jpn J Appl Phys. 2006;45:597–625.
  • Jakli A. Liquid crystals of the twenty-first century–nematic phase of bent-core molecules. Liq Cryst Rev. 2013;1:65–82.
  • Gleeson HF, Kaur S, Gartz V, et al. The Nematic Phases of Bent‐Core Liquid Crystals. ChemPhysChem. 2014;15:1251–1260.
  • Sreenilayam SP, Panov VP, Vij JK, et al. The N-TB phase in an achiral asymmetrical bent-core liquid crystal terminated with symmetric alkyl chain. Liq Cryst. 2017;44:244–253.
  • Kumar S, Gowda AN. The chemistry of bent-core molecules forming nematic liquid crystals. Liq Cryst Rev. 2015;3:99–145. DOI:10.1080/21680396.2015.1061958
  • 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.
  • Shen D, Pegenau A, Diele S, et al. Molecular design of nonchiral bent-core liquid crystals with antiferroelectric properties. J Am Chem Soc. 2000;122:1593–1601.
  • Yu FC, Yu LJ. Mesophases of achiral bent molecules. Chem Mater. 2006;18:5410–5420.
  • Hird M, Raoul Y, Goodby JW, et al. Chirality issues and interesting properties of achiral and racemic materials with bent molecular structures. Ferroelectrics. 2004;309:95–100.
  • Fergusson KM, Hird M. The dramatic influence of the location of bend and of lateral fluoro substitution on the mesomorphic properties of angular chiral esters based on a 1,3-disubstituted benzene ring. J Mater Chem. 2010;20:3069–3078.
  • Fergusson KM, Hird M. A helical liquid crystal phase generated by a chiral ester with a bent-core molecular architecture. Adv Mater. 2007;19:211–214.
  • Hird M, Goodby JW, Gough J, et al. Novel liquid crystals with a bent molecular shape containing a 1,5-disubstituted 2,3,4-trifluorophenyl unit. Banana-shaped liquid crystals—synthesis and properties. J Mater Chem. 2001;11:732–2742.
  • Weissflog W, Dunemann U, Tandel SF, et al. At the boundary to banana-shaped liquid crystals: polar properties of phases formed by new asymmetric achiral four-ring bent-core mesogens. Soft Matter. 2009;5:1840–1847.
  • Kang S, Saito Y, Watanabe N, et al. Low-birefringent, chiral banana phase below calamitic nematic and/or smectic C phases in oxadiazole derivatives. J Phys Chem B. 2006;110:5205–5214.
  • Deb R, Nath RK, Paul MK, et al. Four-ring achiral unsymmetrical bent core molecules forming strongly fluorescent smectic liquid crystals with spontaneous polar and chiral ordered B7 and B1 phases. J Mater Chem. 2010;20:7332–7336.
  • Yoon DK, Deb R, Chen D, et al. Organization of the polarization splay modulated smectic liquid crystal phase by topographic confinement, Proc Natl Acad Sci. Usa. 2010;107:1311–21315.
  • Nath RK, Sarkar DD, Rao DSS, et al. Influence of polar substituents on the mesomorphism of non-symmetrical achiral four-ring bent-core compounds: synthesis and characterisation. Liq Cryst. 2012;39:889–902.
  • Nath RK, Deb R, Chakraborty N, et al. Influence of the chloro substituent on the mesomorphism of unsymmetrical achiral four-ring bent-core compounds: 2D polarization modulated banana phases. J Mater Chem C. 2013;1:663–670.
  • Debnath S, Mohiuddin G, Turlapati S, et al. Nematic phases in achiral unsymmetrical four-ring bent-core azo compounds possessing strongly polar cyano and nitro moieties as end substituents: synthesis and characterization. Dyes and Pigments. 2013;99:447–455.
  • Begum N, Turlapati S, Debnath S, et al. Achiral unsymmetrical four-ring bent-core liquid crystals with a polar fluoro or chloro end substituent: synthesis and characterisation. Liq Cryst. 2013;40:1105–1115.
  • Venkatesh G, Upadhyaya K, Mohiuddin G, et al. A new family of four-ring bent-core nematic liquid crystals with a highly polar end-group. Liq Cryst. 2013;40:120–129.
  • Barbera J, Gimenez R, Serrano JL, et al. beta-Diketone, pyrazole and isoxazole derivatives with polar groups: liquid crystalline and non-linear optical properties. Liq Cryst. 1997;22:265–273.
  • Lee CH, Yamamoto T. Synthesis of liquid crystals with bent-rod structure: 4-methylthiazole derivatives with nematic phase. Mol Cryst Liq Cryst Sci Technol Sect A. 2001;369:95–102.
  • Haino T, Tanaka M, Ideta K, et al. Solid-phase synthesis of liquid crystalline isoxazole library. Tetrahedron Lett. 2004;45:2277–2279.
  • Suisse JM, Bellemin-Laponnaz S, Douce L, et al. A new liquid crystal compound based on an ionic imidazolium salt. Tetrahedron Lett. 2005;46:4303–4305.
  • Wen Y, Zheng Z, Wang H, et al. Photoinduced phase transition behaviours of the liquid crystal blue phase doped with azobenzene bent-shaped molecules. Liq Cryst. 2012;39:509–514.
  • Galardo H, Bortoluzzi AJ, Pereira De O, et al. Synthesis, crystalline structure and mesomorphic properties of new liquid crystalline 1, 2, 3-triazole derivatives. Liq Cryst. 2008;35:719–725.
  • Weissflog W, Baumeister U, Tamba MG, et al. Unexpected liquid crystalline behaviour of three-ring bent-core mesogens: bis (4-subst.-phenyl) 2-methyl-iso-phthalates. Soft Matter. 2012;8:2671–2685.
  • Ahipa TN, Kumar V, Rao DSS, et al. New 4-(2-(4-alkoxyphenyl)-6-methoxypyridin-4-yl) benzonitriles: synthesis, liquid crystalline behavior and photo physical properties. CrystEngComm. 2014;16:5573–5582.
  • Ahipa N, Adhikari AV. 2-Methoxypyridine derivatives: synthesis, liquid crystalline and photo-physical properties. New J Chem. 2014;38:5018–5029.
  • Weissflog W. Comment on the paper ‘Synthesis and mesomorphic properties of three-benzene-ring containing banana-shaped liquid crystals’. Liq Cryst. 2011;38:1081–1083.
  • Mohiuddin G, Punjani V, Pal SK. Three-ring-based room-temperature bent-core nematic compounds: synthesis and characterization. ChemPhysChem. 2015;16:2739–2744.
  • Speetjens F, Lindborg J, Tauscher T, et al. Low nematic onset temperatures and room temperature cybotactic behavior in 1,3,4-oxadiazole-based bent-core mesogens possessing lateral methyl groups. J Mater Chem. 2012;22:22558–22564.
  • Lehmann M, Kang SW, Kohn C, et al. Shape-persistent V-shaped mesogens—formation of nematic phases with biaxial order. J Mater Chem. 2006;16:4326–4334.
  • Lehmann M, Seltmann J, Auer AA, et al. Synthesis and mesomorphic properties of new V-shaped shape-persistent nematogens containing a thiazole or a thiadiazole bending unit. J Mater Chem. 2009;19:1978–1988.
  • Nagaraj M. Dark conglomerate phases of bent core liquid crystals. Liq Cryst. 2016;43:2244–2253.
  • Vita F. Search for nematic biaxiality in bent-core mesogens: an X-ray diffraction perspective. Liq Cryst. 2016;43:2254–2276.
  • Wirth I, Diele S, Eremin A, et al. New variants of polymorphism in banana-shaped mesogens with cyano-substituted central core. J Mater Chem. 2001;11:1642–1650.
  • Keith C, Lehmann A, Baumeister U, et al. Nematic phases of bent-core mesogens. Soft Matter. 2010;6:1704–1721.
  • Kaur S. Elastic properties of bent-core nematic liqud crystals: the role of the bend angle. Liq Cryst. 2016;43:2277–2284.
  • Nandi R, Singh HK, Singh SK, et al. Investigation of liquid crystalline property of a new calamitic liquid crystalline system methyl 4-(4ʹ-(4ʹʹ-(decyloxy) benzyloxy) benzylideneamino) benzoate. Liq Cryst. 2016. DOI:10.1080/02678292.2016.1269959
  • Carlton RJ, Hunter JT, Miller DS, et al. Chemical and biological sensing using liquid crystals. Liq Cryst Rev. 2013;1:29–51.
  • Dąbrowski R. From the discovery of the partially bilayer smectic A phase to blue phases in polar liquid crystals. Liq Cryst. 2015;42:783–818.
  • Csorba K, Vajda A, Jakli A, et al. Ester type banana-shaped liquid crystalline monomers: synthesis and physical properties. J Mater Chem. 2002;12:2499–2506.
  • Kovalenko L, Schroder MW, Reddy RA, et al. Unusual mesomorphic behaviour of new bent-core mesogens derived from 4-cyanoresorcinol. Liq Cryst. 2005;32:857–865.
  • Gray GW, Jones B. The effect of halogen substitution on the mesomorphism of the 4-alkoxybenzoic acids. J Chem Soc. 1954;2556–2562.
  • Ghosh S, Begum N, Turlapati S, et al. Ferroelectric-like switching in the nematic phase of four-ring bent-core liquid crystals. J Mater Chem C. 2014;2:425–431.
  • Hiremath US, Nair GG, Rao DSS. Supramolecular non-symmetric dimmers from cholesterol: synthesis and phase transitional properties. Liq Cryst. 2016;43:711–728.
  • Kaur S, Punjani V, Mohiuddin G, et al. Orthogonal smectic and nematic ordering in three-ring polar bent-core molecules with anti-parallel arrangement. New J Chem. 2017;41:5403–5411.
  • Imrie CT. Laterally substituted dimeric liquid-crystals. Liq Cryst. 1989;6:391–396.
  • Chan T-N, Lu Z, Yamw -S, et al. Non-symmetric liquid crystal dimers containing an isoflavone moiety. Liq Cryst. 2012;39:393–402.
  • Lee H-C, Lu Z, Henderson PA, et al. Cholesteryl-based liquid crystal dimmers containing a sulphur-sulfuur link in the flexible spacer. Liq Cryst. 2012;39:259–268.
  • Ocak H, Bilgin-Eran B, Gu¨Zeller D, et al. Twist grain boundary (TGB) states of chiral liquid crystalline bent-core mesogens. Chem Commun. 2015;51:7512–7515.
  • Havriliak S, Negami S. A complex plane analysis of α-dispersions in some polymer systems. J Polym Sci Part C: Polym Symp. 1966;14:99–117.
  • Hong SH, Verduzco R, Williams JC, et al. Short-range smectic order in bent-core nematic liquid crystals. Soft Matter. 2010;6:4819–4827.
  • Gleeson HF, Kaur S, Gçrtz V, et al. The nematic phases of bent-core liquid crystals. Chem Phys Chem. 2014;15:1251–1260.
  • Guo L, Gomola K, Gorecka E, et al. Transition between two orthogonal polar phases in symmetric bent-core liquid crystals. Soft Matter. 2011;7:2895–2899.

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.