339
Views
16
CrossRef citations to date
0
Altmetric
Original Articles

Non-conventional three-armed star-shaped mesogens based on 1,3,5-trisubstituted benzene with azobenzene moieties at the periphery: synthesis, and mesomorphic behaviour

, , , , &
Pages 1017-1033 | Received 08 Jul 2013, Accepted 23 Feb 2014, Published online: 17 Mar 2014

References

  • Yoshizawa A. Unconventional liquid crystal oligomers with a hierarchical structure. J Mater Chem. 2008;18:2877–2889. doi:10.1039/b802712a
  • Achalkumar AS, Hiremath US, Shankar Rao DS, Yelamaggad CV. Non-conventional liquid crystals: synthesis and mesomorphism of non-symmetric trimers and tetramers derived from cholesterol. Liq Cryst. 2011;38:1563–1589. doi:10.1080/02678292.2011.610473
  • Gemming S, Popov I, Lehmann M. Polymorphism in liquid crystals from star-shaped mesogens. Phil Mag Lett. 2007;87:883–891. doi:10.1080/09500830701537959
  • Yao DS, Zhang BY, Li YH, Xiao WQ. Synthesis and mesomorphism of novel star-shaped glassy liquid crystals containing pentaerythritol esters. Tetrahedron Lett. 2004;45:8953–8956. doi:10.1016/j.tetlet.2004.09.109
  • Tian M, Zhang BY, Cong YH, Zhang N, Yao DS. Mesomorphic properties of multi-arm liquid crystals containing glucose and sorbitol as cores. J Mol Struct. 2009;923:39–44. doi:10.1016/j.molstruc.2009.01.049
  • Shimizu Y, Kurobe A, Monobe H, Terasawa N, Kiyohara K, Uchida K. Calamitic and discotic mesophases formed by kinetically controlled rod-disc alternation of molecular shape in a triphenylene-azobenzene mesogenic system. Chem Comm. 2003;14:1676–1677. doi:10.1039/b301862h
  • Takezoe H, Takanishi Y. Bent-core liquid crystals: their mysterious and attractive world. Jap J App Phys. 2006;45:597–625. doi:10.1143/JJAP.45.597
  • Balamurugan S, Kannan P. Synthesis and characterization of symmetrical banana shaped liquid crystalline polyethers. J Mol Struct. 2009;934:44–52. doi:10.1016/j.molstruc.2009.06.019
  • Wang H, Zheng Z, Shen D. Blue phase liquid crystals induced by bent-shaped molecules based on 1,3,4-oxadiazole derivatives. Liq Cryst. 2012;39:99–103. doi:10.1080/02678292.2011.628704
  • Dingemans TJ, Madsen LA, Francescangeli O, Vita F, Photinos DJ, Poon CD, Samulski ET. The biaxial nematic phase of oxadiazole biphenol mesogens. Liq Cryst. 2013;40:1655–1677. doi:10.1080/02678292.2013.824119
  • Lee HC, Lu Z, Henderson PA, Achard MF, Mahmood WAK, Yeap GY, Imrie CT. Cholesteryl-based liquid crystal dimers containing a sulfur-sulfur link in the flexible spacer. Liq Cryst. 2012;39:259–268. doi:10.1080/02678292.2011.641753
  • Mori A, Kubo K, Takemoto M, Kitaura H, Ujiie S. Dimeric liquid crystals with 5‐(4‐alkoxybenzoyloxy)tropone or 4‐(4‐alkoxybenzoyloxy)phenyl cores: evaluation of the tilt angles of the cores, spacers, and side chains. Liq Cryst. 2006;33:521–530. doi:10.1080/02678290600633253
  • Yeap GY, Al-Taifi EA, Ong CH, Mahmood WAK, Takeuchi D, Ito MM. Synthesis and phase transition studies on non-symmetric liquid crystal dimers: N-(4-(n-(4-(benzothiazol-2-yl)phenoxy)alkyloxy)-benzylidene)-4-chloroanilines. Phase Trans. 2012;85:483–496. doi:10.1080/01411594.2011.624278
  • Henderson PA, Imrie CT. Methylene-linked liquid crystal dimers and the twist-bend nematic phase. Liq Cryst. 2011;38:1407–1414. doi:10.1080/02678292.2011.624368
  • Buzin AI, Makarova NN, Taldrik AV, Malakhova YN, Bushmarinov IS, Antipin MY. Comb-shaped liquid crystalline stereoregular cyclolinear methylsiloxane copolymers: synthesis, behaviour in bulk and behaviour in monolayers. Liq Cryst. 2012;39:133–147. doi:10.1080/02678292.2011.620989
  • Jung BM, Huang YD, Chang JY. Preparation of discotic metallomesogens based on phenacylpyridines showing room temperature columnar phases. Liq Cryst. 2010;37:85–92. doi:10.1080/02678290903390940
  • Rezvani Z, Divband B, Abbasi AR, Nejati K. Liquid crystalline properties of copper(II) complexes derived from azo-containing salicylaldimine ligands. Polyhedron. 2006;25:1915–1920. doi:10.1016/j.poly.2005.12.016
  • Abe Y, Nakazima N, Tanase T, Katano S, Mukai H, Ohta K. Syntheses, structures, and mesomorphism of a series of Cu(II) salen complexes with 4-substituted long alkoxy chains. Mol Cryst Liq Cryst. 2007;466:129–147. doi:10.1080/15421400601150304
  • Lee JH, Han MJ, Hwang SH, Jang I, Lee SJ, Yoo SH, Jho JY, Park SY. Self-assembled discotic liquid crystals formed by hydrogen bonding of alkoxystilbazoles. Tetrahedron Lett. 2005;46:7143–7146. doi:10.1016/j.tetlet.2005.08.094
  • Goldmann D, Janietz D, Schmidt C, Wendorff JH. Columnar liquid crystalline phases through hydrogen bonding and nanoscale segregation. J Mater Chem. 2004;14:1521–1525. doi:10.1039/b400781f
  • Cho CM, Wang X, Li JJ, He C, Xu J. Synthesis and self-assembly of halogen-bond donor-spacer-hydrogen-bond donor molecules: polymeric liquid crystals induced by combination of intermolecular halogen- and hydrogen-bonding interactions. Liq Cryst. 2013;40:185–196. doi:10.1080/02678292.2012.735708
  • Martinez-Felipe A, Lu Z, Henderson PA, Picken SJ, Norder B, Imrie CT, Ribes-Greus A. Synthesis and characterisation of side chain liquid crystal copolymers containing sulfonic acid groups. Polymer. 2012;53:2604–2612. doi:10.1016/j.polymer.2012.02.029
  • Hashim R, Sugimura A, Minamikawa H, Heidelberg T. Nature-likesynthetic alkyl branched-chain glycolipids: a review on chemical structure and self-assembly properties. Liq Cryst. 2012;39:1–17. doi:10.1080/02678292.2011.614017
  • Cook AG, Martinez-Felipe A, Brooks NJ, Seddon JM, Imrie CT. New insights into the transitional behaviour of methyl-6-O-(n-dodecanoyl)-α-D-glucopyranoside using variable temperature FTIR spectroscopy and X-ray diffraction. Liq Cryst. 2013;40:1817–1827. doi:10.1080/02678292.2013.854556
  • Lee JH, Jang I, Hwang SH, Lee SJ, Yoo SH, Jho JY. Self-assembled discotic nematic liquid crystals formed by simple hydrogen bonding between phenol and pyridine moieties. Liq Cryst. 2012;39:973–981. doi:10.1080/02678292.2012.689020
  • Lee JH, Lee HJ, Lee SJ, Jang J, Yoo SH, Jho JY. Preparation of conjugated polymeric columns with a hexagonal symmetry from star-shaped supramolecular liquid crystals. Liq Cryst. 2013;40:112–119. doi:10.1080/02678292.2012.733737
  • Imrie CT, Henderson PA, Yeap GY. Liquid crystal oligomers: going beyond dimers. Liq Cryst. 2009;36:755–777. doi:10.1080/02678290903157455
  • Lehmann M. Star mesogens (Hekates) – Tailor made molecules for programming supramolecular functionality. Chem Eur J. 2009;15:3638–3651. doi:10.1002/chem.200802625
  • Jeong KU, Jing AJ, Monsdorf B, Graham MJ, Harris FW, Cheng SZD. Self-assembly of chemically linked rod−disc mesogenic liquid crystals. J Phys Chem B. 2007;111:767–777. doi:10.1021/jp066274b
  • Imrie CT, Lu Z, Picken SJ, Yildirim Z. Oligomeric rod-disc nematic liquid crystals. Chem Comm. 2007;1245–1247. doi:10.1039/b614922g
  • Lehmann M, Gearba RI, Ivanov DA, Koch MHJ. New star-shaped mesogens with three different arms on a 1,3,5-benzene core. Mol Cryst Liq Cryst. 2004;411:397–406. doi:10.1080/15421400490435422
  • Meier H, Lehmann M, Holst HC, Schwöppe D. Star-shaped conjugated compounds forming nematic discotic systems. Tetrahedron. 2004;60:6881–6888. doi:10.1016/j.tet.2004.06.012
  • Stackhouse PJ, Wilson A, Lacey D, Hird M. 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. doi:10.1080/02678292.2010.490647
  • Zhang BY, Yao DS, Meng FB, Li YH. Structure and properties of novel three-armed star-shaped liquid crystals. J Mol Struct. 2005;741:135–140. doi:10.1016/j.molstruc.2005.01.057
  • Goldmann D, Janietz D, Schmidt C, Wendorff JH. Liquid crystalline 1,3,5-triazines incorporating rod-like azobenzene sub-units. Liq Cryst. 1998;25:711–719. doi:10.1080/026782998205723
  • Salisu AA, Kogo AA. New Liquid crystals in the series of 1,3,5-triazine compounds containing azobenzene at the peripheral arms. Bayero J Pure and Appl Sci. 2010;3:54–58.
  • Yao DS, Zhang BY, Zhang WW, Tian M. A new class of star-shaped cholesteric liquid crystal containing a 1,3,5-trihydroxybenzene unit as a core. J Mol Struct. 2008;881:83–89. doi:10.1016/j.molstruc.2007.08.041
  • Prasad V. Liquid crystalline compounds with V-shaped molecular structures: synthesis and characterization of new azo compounds. Liq Cryst. 2001;28:145–150. doi:10.1080/026782901462481
  • Yeap GY, Balamurugan S, Rakesh S. Synthesis and mesomorphic properties of chiral liquid crystal dimers derived from azobenzene and substituted naphthol. Liq Cryst. 2013;40:555–563. doi:10.1080/02678292.2013.765608
  • Bobrovsky A, Shibaev V. Polarised light-induced orientation and reorientation processes and unexpected ‘memory effect’ in side-chain azobenzene-containing LC polymers. Liq Cryst. 2012;39:339–345. doi:10.1080/02678292.2011.648665
  • Chan TN, Lu Z, Yam WS, Yeap GY, Imrie CT. Non-symmetric liquid crystal dimers containing an isoflavone moiety. Liq Cryst. 2012;39:393–402. doi:10.1080/02678292.2012.658712
  • Yeap GY, Ooi YH, Kenji K, Ito MM. Synthesis and mesomorphic properties of novel three-armed star-shaped mesogens of phloroglucinol (1,3,5-trihydroxybenzene) containing Schiff base moiety. Phase Trans. 2013;86:365–379. doi:10.1080/01411594.2012.683870
  • Al-Hamdani UJ, Gassim TE, Radhy HH. Synthesis and characterization of azo compounds and study of the effect of substituents on their liquid crystalline behavior. Molecules. 2010;15:5620–5628. doi:10.3390/molecules15085620
  • Attard GS, Dave JS, Wallington A, Imrie CT, Karasz FE. Transitional properties of liquid-crystalline side-chain polymers derived from poly(p-hydroxystyrene. Makromol Chem. 1991;192:1495–1508. doi:10.1002/macp.1991.021920704
  • Ha ST, Ng MY, Subramaniam RT, Ito MM, Saito A, Watanabe M, Lee SL, Bonde NL. Mesogenic azomethine esters with different end groups: Synthesis and thermotropic properties. Int J Phy Sci. 2010;5:1256–1262.
  • Dierking I. Textures of liquid crystals. Weinheim: Wiley-VCH; 2003. p. 141–142.
  • Cladis PE, Goodby JW. Pressure study of a hexatic B and crystal B phase. Mol Cryst Liq Cryst. 1982;72:307–312. doi:10.1080/01406568208084725
  • Bao R, Pan M, Qiu JJ, Liu CM. Synthesis and characterization of six-arm star-shaped liquid crystalline cyclotriphosphazenes. Chin Chem Lett. 2010;21:682–685. doi:10.1016/j.cclet.2009.12.020
  • Prajapati AK, Varia MC, Sahoo SP. Azoester-based H-shaped symmetrical mesogenic dimers containing –CH3/-OCH3 terminal substituent. Phase Trans. 2011;84:325–342. doi:10.1080/01411594.2010.537210
  • Henderson PA, Imrie CT. Semiflexible liquid crystalline tetramers as models of structurally analogous copolymers. Macromolecules. 2005;38:3307–3311. doi:10.1021/ma0502304
  • Imrie CT, Luckhurst GR. Liquid crystal trimers. The synthesis and characterisation of the4,4′-bis[ω-(4-cyanobiphenyl-4′-yloxy)alkoxy]biphenyls. J Mater Chem. 1998;8:1339–1343. doi:10.1039/a801128a
  • Yeap GY, Hng TC, Yeap SY, Gorecka E, Ito MM, Ueno K, Okamoto M, Mahmood WAK, Imrie CT. Why do non-symmetric dimers intercalate? The synthesis and characterisation of the α-(4-benzylidene-substituted-aniline-4′-oxy)-ω-(2-methylbutyl-4′-(4″-phenyl)benzoateoxy)alkanes. Liq Cryst. 2009;36:1431–1441. doi:10.1080/02678290903271504
  • Donaldson T, Henderson PA, Achard MF, Imrie CT. Non-symmetric chiral liquid crystal trimers. Liq Cryst. 2011;38:1331–1339. doi:10.1080/02678292.2011.613265
  • Thaker BT, Kanojiya JB, Tandel RS. Effects of different terminal substituents on the mesomorphic behavior of some Azo-Schiff base and Azo-Ester-based liquid crystals. Mol Cryst Liq Cryst. 2010;528:120–137. doi:10.1080/15421406.2010.504632
  • Henderson PA, Niemeyer O, Imrie CT. Methylene-linked liquid crystal dimers. Liq Cryst. 2001;28:463–472. doi:10.1080/02678290010007558
  • Imrie CT, Luckhurst GR. Liquid crystal dimers and oligomers. In: Demus D, Goodby JW, Gray GW, Spiess HW, Vill V, editors. Handbook of liquid crystals, Vol. 2B. Weinheim: Wiley-VCH; 1998. p. 801.
  • Yeap GY, Lee HC, Mahmood WAK, Imrie CT, Takeuchi D, Osakada K. Synthesis, thermal and optical behaviour of non-symmetric liquid crystal dimers α-(4-benzylidene-substituted-aniline-4′-oxy)-ω-[pentyl-4-(4′-phenyl)benzoateoxy]hexane. Phase Trans. 2011;84:29–37. doi:10.1080/01411594.2010.513613
  • Yeap GY, Alshargabi A, Ito MM, Mahmood WAK, Takeuchi D. Synthesis and anisotropic properties of azo-bridged benzothiazole-phenyl esters. Mol Cryst Liq Cryst. 2012;557:126–133. doi:10.1080/15421406.2011.637744
  • Tinh NH, Zann A, Dubois JC. Synthesis of 1-(4-alkoxy or alkyl-benzoyloxy-phenyl)-2-(4′-pentylphenyl)-ethanes. Influence of the central group on the mesomorphic properties. Mol Cryst Liq Cryst. 1979;53:43–54. doi:10.1080/00268947908083982
  • Godzwon J, Sienkowska MJ, Galewski Z. Smectic polymorphism of 4-nonyloxybenzylidene-4′-alkyloxyanilines. J Mol Struct. 2007;844–845:259–267. doi:10.1016/j.molstruc.2007.04.029
  • Yeap GY, Ooi YH, Kubo K, Ito MM. Synthesis and mesomorphic properties of 4-(4-bromopropyloxy)-4′-(4-alkyloxybenzylidene)anilines. Chin Chem Lett. 2012;23:769–772. doi:10.1016/j.cclet.2012.05.008
  • Yelamaggad CV, Shashikala IS, Hiremath US, Shankar Rao DS, Prasad SK. Liquid crystal dimers possessing chiral rod‐like anisometric segments: synthesis, characterization and electro‐optic behaviour. Liq Cryst. 2007;34:153–167. doi:10.1080/02678290601137585
  • Attard GS, Douglass AG, Imrie CT, Taylor L. Liquid crystalline cyclic trimers derived from benzene-1,3,5-tricarboxylic acid. Liq Cryst. 1992;11:779–784. doi:10.1080/02678299208029029
  • Shanavas A, Narasimhaswamy T, Sadiku ER. Three armed star mesogens based on 1,3,5-benzenetricarboxylic acid: synthesis and mesophase characterization. J Mol Struct. 2013;1054–1055:18–24. doi:10.1016/j.molstruc.2013.09.030
  • Rahman L, Kumar S, Tschierske C, Israel G, Ster D, Hegde G. Synthesis and photoswitching properties of bent-shaped liquid crystals containing azobenzene monomers. Liq Cryst. 2009;36:397–407. doi:10.1080/02678290902923428
  • Kang IN, Hwang DH, Shim HK. Synthesis and electrical properties of halogen substituted PPV derivatives. Synthetic Metals. 1995;69:547–548. doi:10.1016/0379-6779(94)02562-D
  • Zhang X, Xu YZ. NMR and UV Studies of 4-thio-2′-deoxyuridine and its derivatives. Molecules. 2011;16:5655–5664. doi:10.3390/molecules16075655

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.