Synthesis and liquid crystal behaviour of tetrathiafulvalenes/1,3-dithiol-2-thione and p-cyanoazobenzene

References

• Piepenbrock MO, Lloyd GO, Clarke N, et al. Metal- and anion-binding supramolecular gels. Chem Rev. 2010;110:1960–2004.
   PubMed Web of Science ®Google Scholar
• Goyal H, Pachisia S, Gupta R. Systematic design of a low-molecular-weight gelator and its application in the sensing and retention of residual antibiotics. Cryst Growth Des. 2020;20:6117–6128.
   Web of Science ®Google Scholar
• Chen L, Mali KS, Puniredd SR, et al. Assembly and fiber formation of a gemini-type hexathienocoronene amphiphile for electrical conduction. J Am Chem Soc. 2013;135:13531–13537.
   PubMed Web of Science ®Google Scholar
• Miyajima D, Araoka F, Takezoe H, et al. Ferroelectric columnar liquid crystal featuring confined polar groups within core-shell architecture. Science. 2012;336:209–213.
   PubMed Web of Science ®Google Scholar
• Love JC, Estroff LA, Kriebel JK, et al. Self-assembled monolayers of thiolates on metals as a form of nanotechnology. Chem Rev. 2005;105:1103–1169.
   PubMed Web of Science ®Google Scholar
• Saegusa T, Sakai H, Nagashima H, et al. Controlled orientations of neighboring tetracene units by mixed self-assembled monolayers on gold nanoclusters for high-yield and long-lived triplet excited states through singlet fission. J Am Chem Soc. 2019;141:14720–14727.
   PubMed Web of Science ®Google Scholar
• Hu G, Kelly SM, Kitney SP, et al. Novel nematic and glassy liquid crystalline oligomers as electroluminescent organic semiconductors. Liq Cryst. 2020. DOI:10.1080/02678292.2020.1800847
   Web of Science ®Google Scholar
• Xu HT, Xia X, Yu WH, et al. Effect of methoxy groups on liquid crystalline and self-assembling properties of 2,7,12-tris(methoxy)-3,8,13-tris(alkoxy)-5,10,15-truxenones. Liq Cryst. 2020. DOI:10.1080/02678292.2020.1766136
   Web of Science ®Google Scholar
• Fan SY, Xu HT, Li QG, et al. Discotic mesogens based on triphenylene-fused benzimidazole or perimidine: facile synthesis, mesomorphism, optical properties and self-assembly. Liq Cryst. 2020;47:1041–1054.
   Web of Science ®Google Scholar
• Pu JL, Yang TZ, Wang YF, et al. Tunable self-organization in n-type liquid crystalline dibenzocoronene tetracarboxdiimides for high photoconductivity. Liq Cryst. 2020;47:291–300.
   Web of Science ®Google Scholar
• Yasuda T, Shimizu T, Liu F, et al. Electro-functional octupolar pi-conjugated columnar liquid crystals. J Am Chem Soc. 2011;133:13437–13444.
   PubMed Web of Science ®Google Scholar
• Li W-S, Yamamoto Y, Fukushima T, et al. Amphiphilic molecular design as a rational strategy for tailoring bicontinuous electron donor and acceptor arrays: photoconductive liquid crystalline oligothiophene-C60 dyads. J Am Chem Soc. 2008;130:8886–8887.
   PubMed Web of Science ®Google Scholar
• Gan KP, Yoshio M, Kato T. Columnar liquid-crystalline assemblies of X-shaped pyrene-oligothiophene conjugates: photoconductivities and mechanochromic functions. J Mater Chem C. 2016;4:5073–5080.
   Web of Science ®Google Scholar
• Domoto Y, Busseron E, Maaloum M, et al. Control over nanostructures and associated mesomorphic properties of doped self-assembled triarylamine liquid crystals. Chem Eur J. 2015;21:1938–1948.
   PubMed Web of Science ®Google Scholar
• Bubnov A, Cigl M, Sedlackova N, et al. Self-assembling behaviour of new functional photosensitive cinnamoyl-based reactive mesogens. Liq Cryst. 2020. DOI:10.1080/02678292.2020.1783586
   Web of Science ®Google Scholar
• Li H, Liu Q, Zhu CY, et al. Photo-induced bending behaviour of side-on linear liquid crystal polymers with high molecular weight. Liq Cryst. 2020;47:1154–1161.
   Web of Science ®Google Scholar
• Zhang XX, Zhang JH, Cong YH, et al. Synthesis, mesomorphic and photo-switching behaviours of novel azobenzene chiral liquid crystals containing (-)-menthyl. Liq Cryst. 2020;47:1345–1353.
   Web of Science ®Google Scholar
• Paterson DA, Xiang J, Singh G, et al. Reversible isothermal twist-bend nematic-nematic phase transition driven by the photoisomerization of an azobenzene-based nonsymmetric liquid crystal dinner. J Am Chem Soc. 2016;138:5283–5289.
   PubMed Web of Science ®Google Scholar
• Aya S, Salamon P, Paterson DA, et al. Fast-and-giant photorheological effect in a liquid crystal dimer. Adv Mater Interfaces. 2019;6:1802032.
   Web of Science ®Google Scholar
• Yoshioka J, Salamon P, Paterson DA, et al. Spherical-cap droplets of a photo-responsive bent liquid crystal dimer. Soft Matter. 2019;15:989–998.
   PubMed Web of Science ®Google Scholar
• Bryce MR. Recent progress on conducting organic charge-transfer salts. Chem Soc Rev. 1991;20:355–390.
   Web of Science ®Google Scholar
• Enoki T, Miyazaki A. Magnetic TTF-based charge-transfer complexes. Chem Rev. 2004;104:5449–5477.
   PubMed Web of Science ®Google Scholar
• Nielsen MB, Lomholt C, Becher J. Tetrathiafulvalenes as building blocks in supramolecular chemistry II. Chem Soc Rev. 2000;29:153–164.
   Web of Science ®Google Scholar
• Imrie CT, Henderson PA, Yeap GY. Liquid crystal oligomers: going beyond dimers. Liq Cryst. 2009;36:755–777.
   Web of Science ®Google Scholar
• Wang L, Jeong KU, Lee MH. Room-temperature columnar liquid crystal based on tetrathiafulvalene. J Mater Chem. 2008;18:2657.
   Web of Science ®Google Scholar
• Miyajima D, Araoka F, Takezoe H, et al. Electric-field-responsive handle for large-area orientation of discotic liquid-crystalline molecules in millimeter-thick films. Angew Chem Int Edit. 2011;50:7865–7869.
   PubMed Web of Science ®Google Scholar
• Zheng N, Li H, Sun G, et al. Synthesis and properties of T-shaped organic conjugates based on 3,6-diarylpyridazine-fused tetrathiafulvalene. Org Biomol Chem. 2013;11:5100–5108.
   PubMed Web of Science ®Google Scholar
• Wang L, Cho H, Lee SH, et al. Liquid crystalline mesophases based on symmetric tetrathiafulvalene derivatives. J Mater Chem. 2011;21:60–64.
   Web of Science ®Google Scholar
• Hou R, Zhong KL, Huang Z, et al. From smectic to columnar phase of polypedal liquid crystals based on tetrathiafulvalene/1,3-dithiol-2-thione and cholesterol. Tetrahedron. 2011;67:1238–1244.
   Web of Science ®Google Scholar
• Wang C, Batsanov AS, Bryce MR, et al. An improved, large-scale (90 g) synthesis of bis(tetraethylammonium)bis(1,3-dithiole-2-thione-4,5-dithiol)zincate: synthesis and X-ray crystal structures of bicyclic and tricyclic 1,4-dithiocines derived from 1,3-dithiole-2-thione-4,5-dithiolate (DMIT). Synthesis-Stuttgart. 1998;11:1615–1618.
   Google Scholar
• Han YK, Dufour B, Wu W, et al. Synthesis and characterization of new liquid-crystalline block copolymers with p-cyanoazobenzene moieties and poly(n-butyl acrylate) segments using atom-transfer radical polymerization. Macromolecules. 2004;37:9355–9365.
   Web of Science ®Google Scholar
• Craig AA, Winchester I, Madden PC, et al. Synthesis, thermal characterization and rheological properties of a homologous series of polymethacrylate-based side-chain liquid crystal polymers. Polymer. 1998;39:1197–1205.
   Web of Science ®Google Scholar
• Imrie CT, Lu ZB, Picken SJ, et al. Oligomeric rod-disc nematic liquid crystals. Chem Commun. 2007;1245–1247. DOI:10.1039/B614922G
   PubMed Web of Science ®Google Scholar
• Donaldson T, Henderson PA, Achard MF, et al. Chiral liquid crystal tetramers. J Mater Chem. 2011;21:10935–10941.
   Web of Science ®Google Scholar
• Chan TN, Lu ZB, Yam WS, et al. Non-symmetric liquid crystal dimers containing an isoflavone moiety. Liq Cryst. 2012;39:393–402.
   Web of Science ®Google Scholar
• Zhang X, Hsu CH, Ren X, et al. Supramolecular [60]fullerene liquid crystals formed by self-organized two-dimensional crystals. Angew Chem Int Edit. 2015;54:114–117.
   PubMed Web of Science ®Google Scholar
• Attard GS, Imrie CT, Karasz FE. Low molar mass liquid-crystalline glasses preparation and properties of the alpha-(4-cyanobiphenyl-4ʹ-oxy)-omega-(1-pyreniminebenzylidene-4ʹ-oxy) alkanes. Chem Mater. 1992;4:1246–1253.
   Web of Science ®Google Scholar
• Attard GS, Imrie CT. Liquid-crystalline and glass-forming dimers derived from 1-aminopyrene. Liq Cryst. 1992;11:785–789.
   Web of Science ®Google Scholar
• Zhong KL, Huang Z, Man Z, et al. Synthesis and self-assembly of rod-coil molecules with n-shaped rod building block. J Polym Sci Pol Chem. 2010;48:1415–1422.
   Web of Science ®Google Scholar
• Kim HJ, Jeong YH, Lee E, et al. Channel structures from self-assembled hexameric macrocycles in laterally grafted bent rod molecules. J Am Chem Soc. 2009;131:17371–17375.
   PubMed Web of Science ®Google Scholar
• Poulsen T, Nielsen KA, Bond AD, et al. Bis(tetrathiafulvalene)-calix[2]pyrrole[2]-thiophene and its complexation with TCNQ. Org Lett. 2007;9:5485–5488.
   PubMed Web of Science ®Google Scholar
• Wang C, Chen Q, Sun F, et al. Multistimuli responsive organogels based on a new gelator featuring tetrathiafulvalene and azobenzene groups: reversible tuning of the gel-sol transition by redox reactions and light irradiation. J Am Chem Soc. 2010;132:3092–3096.
   PubMed Web of Science ®Google Scholar