Influence of mesogenic core polarity and position of chains attachment on columnar phase stability

References

• Chandrasekhar S, Sadashiva BK, Suresh KA. Liquid crystals of disc-like molecules. Pramana. 1977;9:471–480. doi:10.1007/BF02846252.
   Web of Science ®Google Scholar
• Chandrasekhar S, Sadashiva BK, Suresh KA. Disc-like mesogens. J Phys Colloq. 1979;40:C3–124. doi:10.1051/jphyscol:1979325.
   Google Scholar
• Destrade C, Mondon MC, Malthete J. Hexasubstituted triphenylenes: a new mesomorphic order. J Phys Colloq. 1979;40:C3–21. doi:10.1051/jphyscol:1979305.
   Google Scholar
• Scherowsky G, Hua Chen X. Ferroelectric switching in columnar phases of novel chiral discotic liquid crystals. J Mater Chem. 1995;5:417–421.
   Web of Science ®Google Scholar
• Bushby RJ, Kawata K. Liquid crystals that affected the world: discotic liquid crystals. Liq Cryst. 2011;38:1415–1426. doi:10.1080/02678292.2011.603262.
   Web of Science ®Google Scholar
• Pal SK, Setia S, Avinash BS. Triphenylene-based discotic liquid crystals: recent advances. Liq Cryst. 2013;40:1769–1816. doi:10.1080/02678292.2013.854418.
   Web of Science ®Google Scholar
• Göltner C, Pressner D, Müllen K. Liquid-crystalline perylene derivatives as“Discotic Pigments”. Angew Chem Int Ed Engl. 1993;32:1660–1662. doi:10.1002/(ISSN)1521-3773.
   Web of Science ®Google Scholar
• Piechocki C, Simon J, Skoulios A. Annelides. 7. Discotic mesophases obtained from substituted metallophthalocyanines. Toward liquid crystalline one-dimensional conductors. J Am Chem Soc. 1982;104:5245–5247. doi:10.1021/ja00383a050.
   Web of Science ®Google Scholar
• Gregg BA, Fox MA, Bard AJ. Porphyrin octaesters: new discotic liquid crystals. J Chem Soc Chem Commun. 1987;10:1134–1135.
   Google Scholar
• Date RW, Iglesias EF, Rowe KE. Metallomesogens by ligand design. Dalton Trans. 2003;10:1914–1931.
   Web of Science ®Google Scholar
• Lai CK, Serrette AG, Swager TM. Discotic bimetallomesogens: building blocks for the formation of new columnar arrangements of transition metals. J Am Chem Soc. 1992;114:7948–7949. doi:10.1021/ja00046a072.
   Web of Science ®Google Scholar
• Venkatesan K, Kouwer PHJ, Yagi S. Columnar mesophases from half-discoid platinum cyclometalated metallomesogens. J Mater Chem. 2008;18:400–407. doi:10.1039/B714291A.
   Web of Science ®Google Scholar
• Trzaska ST, Swager TM. Columnar mesophases from nondiscoid metallomesogens: rhodium and iridium dicarbonyl diketonates. Chem Mater. 1998;10:438–443. doi:10.1021/cm9706098.
   Web of Science ®Google Scholar
• Kishikawa K, Furusawa S, Yamaki T. Novel superstructure of nondiscoid mesogens: uneven-parallel association of half-disk molecules, 3,4,5-trialkoxybenzoic anhydrides, to a columnar structure and its one-directionally geared interdigitation. J Am Chem Soc. 2002;124:1597–1605. doi:10.1021/ja012156k.
   PubMed Web of Science ®Google Scholar
• Seo J, Kim S, Gihm SH. Highly fluorescent columnar liquid crystals with elliptical molecular shape: oblique molecular stacking and excited-state intramolecular proton-transfer fluorescencje. J Mater Chem. 2007;17:5052–5057.
   Web of Science ®Google Scholar
• Artal MC, Toyne KJ, Goodby J. Synthesis and mesogenic properties of novel board-like liquid crystals. J Mater Chem. 2001;11:2801–2807. doi:10.1039/b105351p.
   Web of Science ®Google Scholar
• Szydłowska J, Krówczyński A, Bilewicz R. Mesogenic binuclear oxamide derivatives with discotic and calamitic properties. J Mater Chem. 2008;18:1108–1115.
   Web of Science ®Google Scholar
• Krowczynski A, Szydlowska J, Pociecha D. Calamitic or columnar mesomorphism determined by number and position of substituents in enaminoketone Cu(II), Ni(II) and Co(II) complexes. Liq Cryst. 1998;25:117–121. doi:10.1080/026782998206560.
   Web of Science ®Google Scholar
• Pietrasik U, Szydłowska J, Krówczyński A. Re-entrant isotropic phase between lamellar and columnar mesophases. J Am Chem Soc. 2002;124:8884–8890. doi:10.1021/ja026234v.
   PubMed Web of Science ®Google Scholar
• Tschierske C. Non-conventional soft matter. Annu Rep Prog Chem Sect C. 2001;97:191–267. doi:10.1039/b101114f.
   Google Scholar
• Praefcke K, Singer D, Gündogan B. Multi-nuclear palladium organyls-novel structures and properties of disc-like metallomesogens 1. Mol Cryst Liq Cryst. 1992;223:181–195. doi:10.1080/15421409208048251.
   Web of Science ®Google Scholar
• Hegmann T, Kain J, Diele S. Molecular design at the calamitic/discotic cross-over point. Mononuclear ortho-metallated mesogens based on the combination of rod-like phenylpyrimidines and -pyridines with bent or half-disc-shaped diketonates. J Mater Chem. 2003;13:991–1003. doi:10.1039/b210250a.
   Web of Science ®Google Scholar
• Pucci D, Crispini A, Ghedini M. 2,2-Biquinolines as test pilots for tuning the colour emission of luminescent mesomorphic silver(I) complexes. Dalton Trans. 2011;40:4614–4622.
   PubMed Web of Science ®Google Scholar
• Głębowska A, Przybylski P, Winek M. Fluorinated metallomesogens – lamellar versus columnar phase formation. J Mater Chem. 2009;16:1395–1398.
   Web of Science ®Google Scholar
• Berardi R, Orlandi S, Zannoni ZC. Monte carlo simulation of discotic gay–berne mesogens with axial dipole. J Chem Soc Faraday Trans. 1997;93:1493–1496. doi:10.1039/a607571a.
   Google Scholar
• Levitsky A, Kishikawa K, Eichhorn SH. Exciton Coupling and dipolar correlations in a columnar liquid crystal: photophysics of a bent-rod hexacatenar mesogen. J Am Chem Soc. 2000;122:2474–2479. doi:10.1021/ja993947d.
   Web of Science ®Google Scholar
• Haase W, Kilian D, Athanassopoulou MA. Enhanced conductivity and dielectric absorption in discotic liquid crystalline columnar phases of a vanadyl complex. Liq Cryst. 2002;29:133–139. doi:10.1080/02678290110093741.
   Web of Science ®Google Scholar
• Foster EJ, Lavigueur C, Ke Y-C Self-assembly of hydrogen-bonded molecules: discotic and elliptical mesogens. J Mater Chem. 2005;15:4062–4068.
   Web of Science ®Google Scholar
• Foster EJ, Jones RB, Lavigueur C. Structural factors controlling the self-assembly of columnar liquid crystals. J Am Chem Soc. 2006;128:8569–8574. doi:10.1021/ja0613198.
   PubMed Web of Science ®Google Scholar
• Lavigueur C, Foster EJ, Williams VE. Self-assembly of discotic mesogens in solution and in liquid crystalline phases: effects of substituent position and hydrogen bonding. J Am Chem Soc. 2008;130:11791–11800. doi:10.1021/ja803406k.
   PubMed Web of Science ®Google Scholar
• Krówczyński A, Krzyczkowska P, Salamończyk M. Mesogenic Ni(II) complexes of Cs symmetry forming Colh phase by dipole-dipole interaction. Liq Cryst. 2012;39:729–737. doi:10.1080/02678292.2012.675597.
   Web of Science ®Google Scholar
• Górecka E, Pyżuk W, Krówczyński A. Smectic polymorphism in a series of three-ring enaminoketone compounds. Liq Cryst. 1993;14:1837–1846. doi:10.1080/02678299308027719.
   Web of Science ®Google Scholar
• Lumbroso H, Liégeois C, Devillanova FA. A dipole moment study of N-methyl and N,N-dimethyl-imidazolidin-2-ones, imidazolidine-2-thiones and −2-selenones. J Mol Structure. 1981;77:239–251. doi:10.1016/0022-2860(81)80068-3.
   Web of Science ®Google Scholar
• Fun H-K, Chinnakali K, Sivakumar K. Substituted methoxybenzene derivatives: C 8 H9NO4, C9H11NO5 and C13H18O4. Acta Cryst C:Cryst Struct Commun. 1997;53:1859–1862. doi:10.1107/S010827019700975X.
   Web of Science ®Google Scholar
• Zeng W-L. 3-(1H-Benzotriazol-1-yl)-1-(4-ethylphenyl)propan-1-one. Acta Cryst E. 2007;E63:o3219. doi:10.1107/S1600536807028632.
   Google Scholar
• Sakho AM, Du D, Li W. Synthesis, crystal structures, and antitumor activity of three new organotin carboxylates. Heteroatom Chem. 2010;21:304–313. doi:10.1002/hc.20614.
   Web of Science ®Google Scholar
• Rego JA, Kumar S, Ringsdorf H. Synthesis and characterization of fluorescent, low-symmetry triphenylene discotic liquid crystals: tailoring of mesomorphic and optical properties. Chem Mater. 1996;8:1402–1409. doi:10.1021/cm950582x.
   Web of Science ®Google Scholar
• Zhu H-P, Yu P-T, Wang Z. (E)-3-(3,4-difluorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one. Acta Cryst E. 2013;E69:o960. doi:10.1107/S1600536813013767.
   Google Scholar
• Kang W, Wu X, Huang HJ. Synthesis, crystal structure and biological activities of four novel tetranuclear di-organotin(IV) carboxylates. J Organomet Chem. 2009;694:2402–2408. doi:10.1016/j.jorganchem.2009.03.025.
   Web of Science ®Google Scholar
• Zhu L-C, Zhao Z-G, Yu S-J. 2-Hydroxy-1,6,7,8-tetramethoxy-3-methylanthraquinone. Acta Cryst. 2008;E64:o371.
   Google Scholar
• Arriortua MI, Via J, Urtiaga MK. Synthesis and crystal structure determination of 3,4-dimethoxybenzyl 2,3,4-trimethoxyphenyl ketone. Bull Soc Chim Belg. 1991;100:361–366. doi:10.1002/bscb.19911000503.
   Google Scholar
• Kozhevnikow VN, Cowling SJ, Karadakov PB. Mesomomorphic1,2,4-triazine-4-oxides in the synthesis of new heterococlic liquid crystals. J Mater Chem. 2008;18:1703–1710.
   Web of Science ®Google Scholar
• Chen C-T, Liao S-Y, Lin K-J. Structural effects on molecular dipoles and solvatochromism of nickel(diimine)(dithiolate) complexes. Inorg Chem. 1999;38:2734–2741. doi:10.1021/ic981125w.
   Web of Science ®Google Scholar
• Demus D, Fujita A, Matsushita MT. The influence of some wing groups on the mesogeneity. Mol Cryst Liq Cryst. 2011;541:3/[241]–259. doi:10.1080/15421406.2011.569312.
   Web of Science ®Google Scholar
• Stephens PJ, Devlin FJ, Chabalowski CF. Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem. 1994;98:11623–11627. doi:10.1021/j100096a001.
   Web of Science ®Google Scholar
• Perdew JP, Burke K, Ernzerhof M. Generalized gradient approximation made simple. Phys Rev Lett. 1996;77:3865–3868. doi:10.1103/PhysRevLett.77.3865.
   PubMed Web of Science ®Google Scholar
• Adamo C, Barone V. Toward reliable density functional methods without adjustable parameters: The PBE0 model. J Chem Phys. 1999;110:6158–6170.
   Web of Science ®Google Scholar
• Tao J, Perdew JP, Staroverov VN. Climbing the density functional ladder: nonempirical meta–generalized gradient approximation designed for molecules and Solids. Phys Rev Lett. 2003;91(14):146401. doi:10.1103/PhysRevLett.91.146401.
   PubMed Web of Science ®Google Scholar
• Lacova M, Loos D, Furdik M. Synthesis and reactions of new 4-oxo-4H-benzopyran-3-carboxaldehydes containing hydroxy groups or 2-oxopyran cycles. Molecules. 1998;3:149–158. doi:10.3390/30600149.
   Web of Science ®Google Scholar
• Ozaki Y, Hosoya A, Okamura K. A convenient synthesis of 2-alkylated 1,4-benzenediols. Synlett. 1997;1997:365–366. doi:10.1055/s-1997-806.
   Google Scholar
• Hauser FM, Ganguly D. Synthetic studies on nogarol anthracyclines. Enantioselective total synthesis of an aminohydroxy epoxybenzoxocin. J Org Chem. 2000;65:1842–1849. doi:10.1021/jo991483w.
   PubMed Web of Science ®Google Scholar
• Barakat AO, Baumgart S, Brocks P. Alkylated phenol series in lacustrine black shales from the Nördlinger Ries, southern Germany. J Mass Spectrom. 2012;47:987–994. doi:10.1002/jms.3049.
   PubMed Web of Science ®Google Scholar
• Brown FJ, Bernstein PR, Cronk LA. Hydroxyacetophenone-derived antagonists of the peptidoleukotrienes. J Med Chem. 1989;32:807–826. doi:10.1021/jm00124a014.
   PubMed Web of Science ®Google Scholar
• Hwang JY, Arnold LA, Zhu F. Improvement of pharmacological properties of irreversible thyroid receptor coactivator binding inhibitors. J Med Chem. 2009;52:3892–3901. doi:10.1021/jm9002704.
   PubMed Web of Science ®Google Scholar
• Tanada Y, Mori K. Synthesis and absolute configuration of (−)-Neuchromenin, a neurotrophic Metabolite of Eupenicillium javanicum var.meloforme, and its enantiomer. Eur J Org Chem. 2001;2001:1963–1966. doi:10.1002/(ISSN)1099-0690.
   Web of Science ®Google Scholar