171
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

The effect of molecular polarity on nem/catic phase stability in 12-vertex carboranes

, , , &
Pages 1188-1198 | Received 13 Feb 2014, Accepted 31 Mar 2014, Published online: 29 Apr 2014

References

  • Kirsch P, Bremer M. Nematic liquid crystals for active matrix displays: molecular design and synthesis. Angew Chem Int Ed. 2000;39:4216–4235. doi:10.1002/1521-3773(20001201)39:23<4216::AID-ANIE4216>3.0.CO;2-K
  • Bremer M, Lietzau L. 1,1,6,7-tetrafluoroindanes: improved liquid crystals for LCD-TV application. New J Chem. 2005;29:72–74. doi:10.1039/b414312d
  • Blinov LM. Behavior of liquid crystals in electric and magnetic fields. In: Demus D, Goodby J, Gray GW, Spiess H-W, Vill V, editors. Hadbook of liquid crystals. Vol. 1. New York (NY): Willey-VCH; 1998. p. 477–534.
  • Blinov LM, Chigrinov VG. Electrooptic effects in liquid crystal materials. New York (NY): Springer-Verlag; 1994.
  • Kaszynski P, Pakhomov S, Gurskii ME, Erdyakov SY, Starikova ZA, Lyssenko KA, Antipin MY, Young VG Jr, Bubnov YN. 1-pyridine- and 1-quinuclidine-1-boraadamantane as models for derivatives of 1-borabicyclo[2.2.2]octane. Experimental and theoretical evaluation of the B–N fragment as a polar isosteric substitution for the C–C group in liquid crystal compounds. J Org Chem. 2009;74:1709–1720. doi:10.1021/jo802504c
  • Ringstrand B, Kaszynski P. How much can an electric dipole stabilize a nematic phase? Polar and non-polar isosteric derivatives of [closo-1-CB9H10]− and [closo-1,10-C2B8H10]. J Mater Chem. 2010;20:9613–9615. doi:10.1039/c0jm02876b
  • Ringstrand B, Kaszynski P. High Δε nematic liquid crystals: fluxional zwitterions of the [closo-1-CB9H10]− cluster. J Mater Chem. 2011;21:90–95. doi:10.1039/c0jm02075c
  • Ringstrand B, Kaszynski P, Young VG Jr. Diazotization of the amino acid [closo-1-CB9H8–1-COOH-6-NH3] and reactivity of the [closo-1-CB9H8–1-COO-6-N2]− anion. Inorg Chem. 2011;50:2654–2660. doi:10.1021/ic102557s
  • Pecyna J, Ringstrand B, Kaszynski P. Synthesis of 12-pyridinium derivatives of the [closo-1-CB11H12] cluster. (submitted).
  • Ringstrand B, Jankowiak A, Johnson LE, Kaszynski P, Pociecha D, Górecka E. Anion-driven mesogenicity: a comparative study of ionic liquid crystals based on the [closo-1-CB9H10]− and [closo-1-CB11H12]− clusters. J Mater Chem. 2012;22:4874–4880. doi:10.1039/c2jm15448j
  • Ringstrand B, Kaszynski P, Young VG Jr, Janoušek JZ. Anionic amino acid [closo-1-CB9H8–1-COO-10-NH3]− and dinitrogen acid [closo-1-CB9H8–1-COOH-10-N2] as key precursors to advanced materials: synthesis and reactivity. Inorg Chem. 2010;49:1166–1179. doi:10.1021/ic9021323
  • Pd-catalyzed amination of the parent [closo-1-CB11H11-12-I] under similar conditions in a microwave oven was recently reported: Konieczka SZ, Himmelspach A, Hailmann M, Finze M. Synthesis, characterization, and selected properties of 7- and 12-ammoniocarba-closo-dodecaboranes. Eur J Inorg Chem. 2013;134–146. doi:10.1002/ejic.201200969
  • Ohta K, Januszko A, Kaszynski P, Nagamine T, Sasnouski G, Endo Y. Structural effects in three-ring mesogenic derivatives of p-carborane and their hydrocarbon analogues. Liq Cryst. 2004;31:671–682. doi:10.1080/02678290410001670584
  • Endo Y, Iijima T, Yamakoshi Y, Fukasawa H, Miyaura C, Inada M, Kubo A, Itai A. Potent estrogen agonists based on carborane as a hydrophobic skeletal structure: a new medicinal application of boron clusters. Chem Biol. 2001;8:341–355. doi:10.1016/S1074-5521(01)00016-3
  • Douglass AG, Pakhomov S, Reeves B, Janoušek Z, Kaszynski P. Triphenylsilyl as a protecting group in the synthesis of 1,12-heterodisubstituted p-carboranes. J Org Chem. 2000;65:1434–1441. doi:10.1021/jo991588z
  • Zhao Y, Truhlar DG. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor Chem Acc. 2008;120:215–241.
  • Chan T-N, Lu Z, Yam W-S, Yeap G-Y, Imrie CT. Non-symmetric liquid crystal dimers containing an isoflavone moiety. Liq Cryst. 2012;39:393–402. doi:10.1080/02678292.2012.658712
  • Kaszynski P, Januszko A, Ohta K, Nagamine T, Potaczek P, Young VG Jr, Endo Y. Conformational effects on mesophase stability: numerical comparison of carborane diester homologous series with their bicyclo[2.2.2]octane, cyclohexane and benzene analogues. Liq Cryst. 2008;35:1169–1190. doi:10.1080/02678290802409775
  • Kaszynski P. Closo-boranes as structural elements for liquid crystals. In: Hosmane N, editor. Boron science: new technologies & applications. New York (NY): CRC Press; 2012. p. 305–338.
  • Gavrilovic DM. United States patent US 3.925.238. 1975; Liqcrys 5.0 database, compound #25521.
  • Januszko A, Glab KL, Kaszynski P, Patel K, Lewis RA, Mehl GH, Wand MD. The effect of carborane, bicyclo[2.2.2]octane and benzene on mesogenic and dielectric properties of laterally fluorinated three-ring mesogens. J Mater Chem. 2006;16:3183–3192. doi:10.1039/b600068a
  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, revision A.02. Wallingford (CT): Gaussian; 2009.
  • Simon S, Duran M, Dannenberg JJ. How does basis set superposition error change the potential surfaces for hydrogen-bonded dimers? J Chem Phys. 1996;105:11024–11031. doi:10.1063/1.472902
  • Cossi M, Scalmani G, Rega N, Barone V. New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution. J Chem Phys. 2002;117:43–54 and references therein. doi:10.1063/1.1480445
  • Pecyna J, Kaszyński P, Ringstrand B, Bremer M. Investigation of high Δε derivatives of the [closo-1-CB9H10]− anion for liquid crystal display applications. J Mater Chem C. 2014;2:2956–2964. doi:10.1039/c4tc00230j
  • Kaszynski P, Huang J, Jenkins GS, Bairamov KA, Lipiak D. Boron clusters in liquid crystals. Mol Cryst Liq Cryst. 1995;260:315–332. doi:10.1080/10587259508038705
  • Burns DH, Miller JD, Chan H-K, Delaney MO. Scope and utility of a new soluble copper catalyst [CuBr–LiSPh–LiBr–THF]: a comparison with other copper catalysts in their ability to couple one equivalent of a grignard reagent with an alkyl sulfonate. J Am Chem Soc. 1997;119:2125–2133. doi:10.1021/ja963944q

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.