145
Views
0
CrossRef citations to date
0
Altmetric
Design of New Materials

Synthesis of achiral rod-shaped triazolic molecules and investigation of their striped texture and propeller-patterned nematic droplets

, , & ORCID Icon
Pages 1324-1332 | Received 30 Jan 2023, Accepted 07 Apr 2023, Published online: 24 Apr 2023

References

  • Geelhaar T, Griesar K, Reckmann B. 25 Years of liquid crystals-a scientific revolution in the home. Angew Chem Int Ed. 2013;52(34):8798–8809.
  • Bahadur B. Liquid crystals: applications and uses. Vol. 2. London (UK): World Scientific; 1992.
  • Demus D, Goodby JW, Gray GW, et al. Handbook of liquid crystals. Vol. 2A, Low molecular weight liquid crystals I: calamitic liquid crystals. Weinheim: Wiley-VcH; 2011.
  • Ghosh T, Lehmann M. Recent advances in heterocycle-based metal-free calamitics. J Mater Chem C. 2017;5:12308–12337.
  • Titov VV, Pavlyuchenko AI. Thermotropic liquid crystals in the heterocyclic series (review). Chem Heterocycl Compd. 1980;16:1–13.
  • Roy B, De N, Majumdar KC. Advances in metal-free heterocycle-based columnar liquid crystals. Chem A Eur J. 2012;18(46):14560–14588.
  • Han J, Wang JY, Zhang FY, et al. Synthesis and mesomorphic behaviour of heterocycle-based liquid crystals containing 1, 3, 4-oxadiazole/thiadiazole and thiophene units. Liq Cryst. 2008;35(10):1205–1214.
  • Rodrigues LD, Sunil D, Chaithra D, et al. 1,2,3/1,2,4-Triazole containing liquid crystalline materials: an up-to-date review of their synthetic design and mesomorphic behavior. J Mol Liq. 2020;297:111909–111951.
  • Juríček M, Kouwera PHJ, Rowan AE. Triazole: a unique building block for the construction of functional materials. Chem Commun. 2011;47:8740–8749.
  • Hua Y, Flood AH. Click chemistry generates privileged CH hydrogen-bonding triazoles: the latest addition to anion supramolecular chemistry. Chem Soc Rev. 2010;39:1262–1271.
  • Schulze B, Schubert US. Beyond click chemistry – supramolecular interactions of 1,2,3-triazoles. Chem Soc Rev. 2014;43:2522–2571.
  • Pedersen DS, Abell A. 1,2,3-triazoles in peptidomimetic chemistry. Eur J Org Chem. 2011;2011(13):2399–2411.
  • Xiong D, Xiong X, Chen Z, et al. Mesophase behaviour of 1,2,3-triazole-based nematic liquid crystals influenced by varying alkyl chains and halogen atom substitution. Liq Cryst. 2022;49(10):1261–1274.
  • Dhingra S, Bala I, De J, et al. An electron-deficient tris(triazole)-based discotic liquid crystal that exhibits fast electron transport. J Mater Chem C. 2021;9:5628–5632.
  • Gimeno N, Martín-Rapún R, Rodríguez-Conde S, et al. Click chemistry as a versatile route to synthesize and modulate bent-core liquid crystalline materials. J Mater Chem. 2012;22:16791–16800.
  • Cristiano R, De Oliveira Santos DMP, Conte G, et al. 1,4-Diaryl and Schiff’s base [1,2,3]- triazole derivative liquid crystalline compounds. Liq Cryst. 2006;33:997–1003.
  • Benbayer C, Kheddam N, Saïdi-Besbes S, et al. Synthesis and mesomorphic properties of novel [1,2,3]- triazole mesogenic based compounds. J Mol Struct. 2013;1034:22–28.
  • Benallou S, Saidi-Besbes S, Grelet E, et al. [1,2,3]-triazole derivatives: mesomorphic property dependence on the molecular shape. Mol Cryst Liquid Cryst. 2017;647(1):290–298. DOI:10.1080/15421406.2017.1289614
  • Benbayer C, Saïdi-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. DOI:10.1080/02678292.2013.822111
  • 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. DOI:10.1080/02678292.2015.1124463
  • Yoon HG, Dierking I, Gleeson HF. Cholesteric pitch divergence near smectic phase transitions. Phys Rev E. 2010;82:011705–011709.
  • Demus D, Richter L. Textures of liquid crystals. Weinheim: Verlag Chemie; 1978.
  • Allet C, Kleman M, Vidal P. Striped patterns in a thin droplet of a smectic C phase. Le Journal de Physique. 1978;39:181–188.
  • Fournier JB, Galatola P. Undulation instability of the interface between a smectic-C liquid crystal and its isotropic or nematic melt. J Phys II France. 1995;5:1297–1320.
  • Seul M, Andelman D. Domain shapes and patterns: the phenomenology of modulated phases. Science. 1995;267:476–483.
  • Galatola P, Fournier JB, Durand G. Spontaneous undulation of equilibrium interfaces with positive surface stiffness. Phy Rev Lett. 1994;3(16):2212–2215.
  • Okano K, Aya S, Araoka F, et al. Photoresponsive stripe pattern in achiral azobenzene liquid crystals. Chem Phys Chem. 2015;16:95–98.
  • Maclenna JE, Sohling U, Clark NA, et al. Textures in hexatic films of nonchiral liquid crystals: symmetry breaking and modulated phases. Phys Rev E. 1994;49:3207–3224.
  • Demikhov EI, Dolganov VK. Length scale dependence of chiral symmetry breaking in free-standing films of achiral smectic C. JETP Lett. 1996;64:32–36.
  • Tschierske C, Ungar G. Mirror symmetry breaking by chirality synchronisation in liquids and liquid crystals of achiral molecules. Chem Phys Chem. 2016;17:9–26.
  • Tschierske C. Mirror symmetry breaking in liquids and liquid crystals. Liq Cryst. 2018;45(13–15):2221–2252.
  • Goodby JW. Chirality in liquid crystals. J Mater Chem. 1991;1:307–318.
  • Salamończyk M, Vaupotič N, Pociecha D, et al. Multi-level chirality in liquid crystals formed by achiral molecules. Nat Commun. 2019;10:1922–1929.
  • Darren RL, Natale G, Shao R, et al. Spontaneous formation of macroscopic chiral domains in a fluid smectic phase of achiral molecules. Science. 1997;278:1924–1927.
  • Takezoe H. Spontaneous achiral symmetry breaking in liquid crystalline phase. Top Curr Chem. 2012;318:303–330.
  • Alasaar M, Prehm M, Nagaraj M, et al. A liquid crystalline phase with uniform tilt, local polar order and capability of symmetry breaking. Adv Mater. 2013;25:2186–2191.
  • Dantlgraber G, Eremin A, Diele S. Chirality and macroscopic polar order in a ferroelectric smectic liquid-crystalline phase formed by achiral polyphilic bent-core molecules this work was supported by the deutsche forschungsgemeinschaft and the fonds der chemischen industrie. Angew Chem Int Ed. 2002;41:2408–2412.
  • Hough LE, Spannuth M, Nakata M. Chiral isotropic liquids from achiral molecules. Science. 2009;325:452–456.
  • Görtz V, Goodby JW. Enantioselective segregation in achiral nematic liquid crystals. Chem Commun. 2005;26:3262–3264.
  • Heppke G, Moro D. Chiral order from achiral molecules. Science. 1998;279:1872–1873.
  • Reddya RA, Tschierske C. Bent-core liquid crystals: polar order, superstructural chirality and spontaneous desymmetrisation in soft matter systems. Mater Chem. 2006;16:907–961.
  • Eremina A, Jákli A. Polar bent-shape liquid crystals–from molecular bend to layer splay and chirality. Soft Matter. 2013;9:615–637.
  • Pelzl G, Eremin A, Diele S, et al. Spontaneous chiral ordering in the nematic phase of an achiral banana-shaped compound. J Mater Chem. 2002;12:2591–2593.
  • Jeong KU, Yang DK, Graham MJ, et al. Construction of chiral propeller architectures from achiral molecules. Adv Mater. 2006;18:3229–3232.
  • Jakli A, Nair GG, Lee CK, et al. Macroscopic chirality of a liquid crystal from nonchiral molecules. Phys Rev E. 2001;63:061710–061710.5.
  • Nagayama H, Varshney SK, Goto M, et al. Spontaneous deracemization of disc‐like molecules in the columnar phase. Angew Chem Int Ed. 2010;49:445–448.
  • Jeong HS, Tanaka S, Yoon DK, et al. Spontaneous chirality induction and enantiomer separation in liquid crystals composed of achiral rod-shaped 4-arylbenzoate esters. J Am Chem Soc. 2009;131:15055–15060.
  • Choi S-W, Fukuda K, Nakahara S, et al. Amplification of twisting power in chiral mesophase by introducing achiral rod-like compound with ester group. Chem Lett. 2006;35:896–897.
  • Kawauchi S, Choi S-W, Fukuda K, et al. Why achiral rod-like compound with ester group amplifies chiral power in chiral mesophase. Chem Lett. 2007;36:750–751.

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.