Self-assembled star-shaped liquid crystals based on 1,3,5-trihydroxybenzene with pendant alkyloxylated azobenzene arms

References

• Tschierske C. Non-conventional liquid crystals - the importance of micro-segregation for self-organisation. J Mater Chem. 1998;8(7):1485–1508.
   Web of Science ®Google Scholar
• Lehmann M. Star-shaped mesogens - hekates: the most basic star structure with three branches in liquid crystals: materials design and self-assembly. Top Curr Chem. 2012;138:193–223.
   Google Scholar
• Attard GS, Douglass AG, Imrie CT, et al. Liquid crystalline cyclic trimers derived from benzene-1,3,5-tricarboxylic acid. Liq Cryst. 1992;11:779–784.
   Web of Science ®Google Scholar
• Lehmann M. Star mesogens (Hekates)-tailor-made molecules for programming supramolecular functionality. Chem Eur J. 2009;15(15):3638–3651.
   PubMed Web of Science ®Google Scholar
• Salisu AA, Kogo AA. New liquid crystals in the series of 1,3,5-triazine compounds containing azobenzene at the peripheral arms. Bay J Pure Appl Sci. 2010;3:54–58.
   Google Scholar
• Salisu AA. Synthesis and mesomorphic properties of a disc-shaped 1,3,5-triazine liquid crystal containing azobenzene at the peripheral arms. Int J Pure Appl Sci. 2008;2(3):119–124.
   Google Scholar
• Stackhouse PJ, Wilson A, Lacey D, et al. Synthesis and properties of novel columnar liquid crystals based on symmetrical and non-symmetrical 1,3,5-trisubstituted benzene derivatives. Liq Cryst. 2010;37:1191–1203.
   Web of Science ®Google Scholar
• Tian M, Zhang BY, Cong YH, et al. Mesomorphic properties of multi-arm liquid crystals containing glucose and sorbitol as cores. J Mol Struct (Theochem). 2009;923:39–44.
   Web of Science ®Google Scholar
• Yao DS, Zhang BY, Zhang WW, et al. A new class of star-shaped cholesteric liquid crystal containing a 1,3,5-trihydroxybenzene unit as a core. J Mol Struct (Theochem). 2008;881:83–89.
   Web of Science ®Google Scholar
• Lehmann M, Dechant M, Gerbig L, et al. Supramolecular click procedures in liquid crystals. Liq Cryst. 2019;46:1985–1994.
   Web of Science ®Google Scholar
• Chen XS, Tao HZ, Dong L, et al. Mesomorphic properties of non-symmetric three-arm chenodeoxycholic acid-derived liquid crystals. Liq Cryst. 2019;46:442–453.
   Web of Science ®Google Scholar
• Kausar A, Nagano H, Ogata T, et al. Photocontrolled translational motion of a microscale solid object on azobenzene-doped liquid-crystalline films. Angew.Chem.Int.Ed. 2009;48:2144–2147.
   PubMed Web of Science ®Google Scholar
• Baroncini M, d’Agostino S, Bergamini G, et al. Photoinduced reversible switching of porosity in molecular crystals based on star-shaped azobenzene tetramers. Nat Chem. 2015;7:634–640.
   PubMed Web of Science ®Google Scholar
• Goulet-Hanssens A, Eisenreich F, Hecht S. Enlightening materials with photoswitches. Adv Mater. 2020;1905966. DOI:10.1002/adma.201905966
   Web of Science ®Google Scholar
• Goldmann D, Janietz D, Schmidt C, et al. Liquid crystalline 1,3,5-triazines incorporating rod-like azobenzene sub-units. Liq Cryst. 1998;25(6):711–719.
   Web of Science ®Google Scholar
• Lehmann M, Gearba RI, Ivanov DA, et al. New star-shaped mesogens with three different arms on a 1,3,5-benzene core. Mol Cryst Liq Cryst. 2004;411:397–406.
   Web of Science ®Google Scholar
• Majumdar KC, De N, Roy B, et al. Synthesis and mesophase characterisation of a series of new triazine-based disc-shaped molecules. Liq Cryst. 2010;37(11):1459–1464.
   Web of Science ®Google Scholar
• Meier H, Lehmann M, Holst HC, et al. Star-shaped conjugated compounds forming nematic discotic systems. Tetrahedron. 2004;60(32):6881–6888.
   Web of Science ®Google Scholar
• Shimizu Y, Kurobe A, Monobe H, et al. Calamitic and discotic mesophases formed by kinetically controlled rod-disc alternation of molecular shape in a triphenyleneazobenzene mesogenic system. Chem Commun. 2003;14:1676–1677.
   Web of Science ®Google Scholar
• Tian M, Zhang BY, Cong YH, et al. Cholesteric star-shaped liquid crystals induced by a maltose core: synthesis and characteristics. Liq Cryst. 2010;37:1373–1379.
   Web of Science ®Google Scholar
• Yeap GY, Ooi YH, Kenji K, et al. Synthesis and mesomorphic properties of novel three-armed star-shaped mesogens of phloroglucinol (1,3,5-trihydroxybenzene) containing Schiff-base moiety. Phase Transit. 2013;86(4):365–379.
   Web of Science ®Google Scholar
• Zhang BY, Yao DS, Meng FB, et al. Structure and properties of novel three armed star-shaped liquid crystals. J Mol Struct. 2005;741:135–140.
   Web of Science ®Google Scholar
• Cheng XH, Diele S, Tschierske C. Molecular design of liquid-crystalline block molecules: semifluorinated pentaerythritol tetrabenzoates exhibiting lamellar, columnar, and cubic mesophases. Angew Chem Int Ed. 2000;39(3):592–595.
   PubMed Web of Science ®Google Scholar
• Miniewicz A, Gniewek A, Parka J. Liquid crystals for photonic applications. Opt Mater. 2003;21:605–610.
   Web of Science ®Google Scholar
• van de Craats AM, Stutzmann N, Bunk O, et al. Meso-epitaxial solution-growth of self-organizing discotic liquid-crystalline semiconductors. Adv Mater. 2003;15:495–499.
   Web of Science ®Google Scholar
• Gemming S, Lehmann M, Seifert G. Semi-flexible star-shaped molecules: conformational analysis of nano-segregated mesogens forming columnar liquid-crystal phases. Z Metallkd. 2005;96:988–997.
   Google Scholar
• Percec V, Glodde M, Peterca M, et al. Self-assembly of semifluorinated dendrons attached to electron-donor groups mediates their π-stacking via a helical pyramidal column. Chem Eur J. 2006;12(24):6298–6314.
   PubMed Web of Science ®Google Scholar
• Percec V, Glodde M, Bera TK, et al. Self-organization of supramolecular helical dendrimers into complex electronic materials. Nature. 2002;419(6905):384–387.
   PubMed Web of Science ®Google Scholar
• Percec V, Holerca MN, Uchida S, et al. Exploring and expanding the three-dimensional structural diversity of supramolecular dendrimers with the aid of libraries of alkali metals of their AB(3) minidendritic carboxylates. Chem Eur J. 2002;8(5):1106–1117.
   PubMed Web of Science ®Google Scholar
• Lehmann M, Gearba RI, Koch MHJ, et al. Semiflexible star-shaped mesogens as nonconventional columnar liquid crystals. Chem Mater. 2004;16(3):374–376.
   Web of Science ®Google Scholar
• Ooi YH, Yeap GY, Han CC, et al. Synthesis and smectogenic properties of novel phloroglucinol-based star-shaped liquid crystals containing three peripheral alkyloxylated Schiff base arms. Liq Cryst. 2013;40(4):516–527.
   Web of Science ®Google Scholar
• El Mansoury A, Bushby RJ, Karodia N. Triphenylene-based discotic liquid crystals: star-shaped oligomers and branched-chain polymers. Liq Cryst. 2012;39(10):1222–1230.
   Web of Science ®Google Scholar
• He XZ, Han L, Meng FB, et al. The effect of different arms on the properties of chiral branched-arm liquid crystals based on isosorbide as the chiral core. Liq Cryst. 2012;39(6):779–787.
   Web of Science ®Google Scholar
• Kumar S, Manickam M. Preliminary communication first example of a functionalized triphenylene discotic trimer: molecular engineering of advanced materials. Liq Cryst. 1999;26(6):939–941.
   Web of Science ®Google Scholar
• Olate FA, Parra ML, Vergara JM, et al. Star-shaped molecules as functional materials based on 1,3,5-benzenetriesters with pendant 1,3,4-thiadiazole groups: liquid crystals, optical, solvatofluorochromic and electrochemical properties. Liq Cryst. 2017;44:1173–1184.
   Web of Science ®Google Scholar
• Pathak SK, Pradhan B, Gupta RK, et al. Aromatic π–π driven supergelation, aggregation induced emission and columnar self-assembly of star-shaped 1,2,4-oxadiazole derivatives. J Mater Chem C. 2016;4:6546–6561.
   Web of Science ®Google Scholar
• Westphal E, Prehm M, Bechtold IH, et al. Room temperature columnar liquid crystalline phases of luminescent non-symmetric star-shaped molecules containing two 1,3,4-oxadiazole units. J Mater Che C. 2013;1(48):8011–8022.
   Web of Science ®Google Scholar
• Nguyen ML, Kim HJ, Cho BK. Peripheral chain length-dependent complex phase behaviour in C-3-symmetric hexa-alkylated liquid crystals. Liq Cryst. 2018;45:1196–1209.
   Web of Science ®Google Scholar
• Obsiye A, Wohrle T, Haenle JC, et al. Dendrimeric triphenylbenzenes: helical versus zig-zag arrangement in columnar mesophases. Liq Cryst. 2018;45:164–172.
   Web of Science ®Google Scholar
• Olate FA, Ulloa JA, Vergara JM, et al. Columnar liquid crystalline tris-(ether)triazines with pendant 1,3,4-thiadiazole groups: synthesis, mesomorphic, luminescence, solvatofluorochromic and electrochemical properties. Liq Cryst. 2016;43(6):811–827.
   Web of Science ®Google Scholar
• Wohrle T, Taing H, Schilling C, et al. Phase behaviour of star-shaped binary mixtures of triphenylbenzenes, triphenylboroxines and triphenyltriazines. Liq Cryst. 2019;46:1973–1984.
   Web of Science ®Google Scholar
• Pradhan B, Pathak SK, Gupta RK, et al. Star-shaped fluorescent liquid crystals derived from s-triazine and 1,3,4-oxadiazole moieties. J Mat Chem C. 2016;4(25):6117–6130.
   PubMed Web of Science ®Google Scholar
• Beltran E, Serrano JL, Sierra T, et al. Functional star-shaped tris(triazolyl)triazines: columnar liquid crystal, fluorescent, solvatofluorochromic and electrochemical properties. J Mater Chem. 2012;22:7797–7805.
   Web of Science ®Google Scholar
• Ge LN, Xian SW, Huang Y, et al. Synthesis and mesomorphism of novel multi-arm liquid crystals with cholic acid as chiral centre linking schiff base moieties as mesogens. Liq Cryst. 2018;45:1055–1067.
   Web of Science ®Google Scholar
• Roth S, Lehman M. Mesogenic origami – four-armed, star-shaped mesogens as precursors for functional liquid crystal materials. Liq Cryst. 2017;44:1830–1851.
   Web of Science ®Google Scholar
• Imrie CT, Lu ZB, Picken SJ, et al. Oligomeric rod–disc nematic liquid crystals. Chem Comm. 2007;12:1245–1247.
   PubMed Web of Science ®Google Scholar
• Chang JY, Yeon JR, Shin YS, et al. Synthesis and characterization of mesogenic disklike benzenetricarboxylates containing diacetylenic groups and their polymerization. Chem Mater. 2000;12(4):1076–1082.
   Web of Science ®Google Scholar
• Lee JH, Han MJ, Hwang SH, et al. Self-assembled discotic liquid crystals formed by hydrogen bonding of alkoxystilbazoles. Tetrahedron Lett. 2005;46:7143–7146.
   Web of Science ®Google Scholar
• Lee JH, Jang I, Hwang SH, et al. Self-assembled discotic nematic liquid crystals formed by simple hydrogen bonding between phenol and pyridine moieties. Liq Cryst. 2012;39:973–981.
   Web of Science ®Google Scholar
• Tang XQ, Bai L, Kong SW, et al. Multi-arm ionic liquid crystals formed by cholesteric mesophase and pyridinium groups. Liq Cryst. 2019;46:1252–1265.
   Web of Science ®Google Scholar
• Wang XD, Bai L, Kong SW, et al. Star-shaped supramolecular ionic liquid crystals based on pyridinium salts. Liq Cryst. 2019;46:512–522.
   Web of Science ®Google Scholar
• Ooi YH, Yeap GY, Han CC, et al. Non-conventional three-armed star-shaped mesogens based on 1,3,5-trisubstituted benzene with azobenzene moieties at the periphery: synthesis, and mesomorphic behavior. Liq Cryst. 2014;41(7):1017–1033.
   Web of Science ®Google Scholar
• Yeap GY, Ooi YH, Uchida N, et al. Symmetrical trimeric star-shaped mesogens based on 1,3,5-trisubstituted benzene incorporating schiff base and azobenzene fragments as the peripheral units: synthesis and mesomorphic properties. J Chem Sci. 2014;126(3):847–859.
   Web of Science ®Google Scholar
• Ooi Y-H, Yeap G-Y, Takeuchi D. Synthesis, mesomorphic properties and structural studies on 1,3,5-trisubstituted benzene-based star-shaped derivatives containing schiff base ester as the peripheral arm. J Mol Struct. 2013;1051:361–375.
   Web of Science ®Google Scholar
• Simion G, Iuganu DF, Carlescu I, et al. Synthesis and Characterization of Some Azo Aromatic Acid Chlorides with Liquid Crystalline Properties. Bul.Inst. Polit. Iași, s. Chemistry and Chemical Engineering. 2011; LVII (LXI), 3: 213 – 219.
   Google Scholar
• Lee SJ, You MK, Lee SW, et al. Star-shaped supramolecular liquid crystals formed by hydrogen bonding between phloroglucinol and stillbazole derivatives with different molecular shapes. Liq Cryst. 2011;38(10):1289–1299.
   Web of Science ®Google Scholar
• Lee SJ, Park CR, Chang JY. Molecular aggregation of disklike benzenetricarboxamides containing diacetylenic groups in bulk and organic solvents. Langmuir. 2004;20(22):9513–9519.
   PubMed Web of Science ®Google Scholar
• Lisa G, Cioanca ER, Tudorachi N, et al. Thermal degradation of some [1,3,4]oxadiazole derivatives with liquid crystalline properties. Themochim Acta. 2011;524:179–185.
   Web of Science ®Google Scholar
• Ciobanu CI, Drochioiu G, Carlescu I, et al. Thermal behavior of some bent-core resorcinol derivatives with azo-type spacers and variable flexible chain. Lett Org Chem. 2016;13:156–161.
   Web of Science ®Google Scholar
• Imrie CT, Taylor L. The preparation and properties of low molar mass liquid-crystals possessing lateral alkyl chains. Liq Cryst. 1989;6(1):1–10.
   Web of Science ®Google Scholar
• Dierking I. Textures of liquid crystals. Weinheim (Germany): Wiley-VCH; 2003.
   Google Scholar
• Laschat S, Baro A, Steinke N, et al. Discotic liquid crystals: from tailor-made synthesis to plastic electronics. Angew Chem Int Ed. 2007;46:4832–4887.
   PubMed Web of Science ®Google Scholar
• Chandrasekhar S, Sadashiva BK, Suresh KA. Liquid crystals of disk-like molecules. Pramana. 1977;9(5):471–480.
   Web of Science ®Google Scholar
• Chang JY, Baik JH, Lee CB, et al. Liquid crystals obtained from disclike mesogenic diacetylenes and their polymerization. J Am Chem Soc. 1997;119(13):3197–3198.
   Web of Science ®Google Scholar
• Materials Studio 4.0. Dassault Systèmes BIOVIA. San Diego: Materials Studio 4.0. licensed to Nicolae Hurduc, 2007.
   Google Scholar
• Tschierske C. Liquid crystals: materials design and self-assembly, series topics in current chemistry 318. Ed. Springer-Verlag Berlin Heidelberg. 0340-1022, 2012.
   Google Scholar