Synthesis of ferrocene derivatives exhibiting low-temperature mesomorphism

References

• Hudson SA, Maitlis PM. Calamitic metallomesogens: metal-containing liquid crystals with rodlike shapes. Chem Rev. 1993;93:861–885.
   Web of Science ®Google Scholar
• Espinet P, Esteruelas MA, Oro LA, Serrano JL, Sola E. Transition metal liquid crystals: advanced materials within the reach of the coordination chemist. Coord Chem Rev. 1992;117:215–274.
   Web of Science ®Google Scholar
• Piechocki C, Simon J, Skoulios A, Guillon D, Weber P. Annelides. 7. Discotic mesophases obtained from substituted metallophthalocyanines. Toward liquid crystalline one-dimensional conductors. J Am Chem Soc. 1982;104:5245–5247.
   Web of Science ®Google Scholar
• Bhatt J, Fung BM, Nicholas KM, Poon CD. Novel ferrocene diesters with liquid-crystal properties. J Chem Soc Chem Commun. 1988;21:1439.
   Google Scholar
• Deschenaux R, Goodby JW. Ferrocene-containing thermotropic liquid crystals. In: Hayashi T, Togni A, editors. Ferrocenes: from homogeneous catalysis to materials science. Weinheim: VCH; 1995. p. 471–495.
   Google Scholar
• Chuard T, Cowling SJ, Fernandez-Ciurleo M, Jauslin I, Goodby JW, Deschenaux R. Planar chirality: a fascinating symmetry breaking which leads to ferroelectricity in ferrocenyl liquid crystals. Chem Commun. 2000;21:2109–2110.
   Web of Science ®Google Scholar
• Brettar J, Bürgi T, Donnio B, Guillon D, Klappert R, Scharf T, Deschenaux R. Ferrocene-containing optically active liquid-crystalline side-chain polysiloxanes with planar chirality. Adv Funct Mater. 2006;16:260–267.
   Web of Science ®Google Scholar
• Deschenaux R, Turpin F. Ferrocene-containing thermotropic side-chain liquid-crystalline polymethacrylate from a mesomorphic trisubstituted ferrocene monomer. Macromolecules. 1997;30: 3759–3765.
   Web of Science ®Google Scholar
• Deschenaux R, Jauslin I, Scholten U, Turpin F. Ferrocene-containing thermotropic side-chain liquid-crystalline polysiloxanes. Macromolecules. 1998;31:5647–5654.
   Web of Science ®Google Scholar
• Deschenaux R, Schweissguth M, Levelut AM. Electron-transfer induced mesomorphism in the ferrocene-ferrocenium redox system: first ferrocenium-containing thermotropic liquid crystal. Chem Commun. 1996;11:1275–1276.
   Web of Science ®Google Scholar
• Deschenaux R, Schweissguth M, Vilches MT. Switchable mesomorphic materials based on the ferrocene-ferrocenium redox system: electron-transfer-generated columnar liquid-crystalline phases. Organometallics. 1999;18:5553–5559.
   Web of Science ®Google Scholar
• Turpin F, Guillon D, Deschenaux R. Switchable liquid-crystalline polymers based on the ferrocene-ferrocenium redox system. Mol Cryst Liq Cryst. 2001;362:171–175.
   Web of Science ®Google Scholar
• Deschenaux R, Serrano E, Levelut AM. Ferrocene-containing liquid-crystalline dendrimers: a novel family of mesomorphic macromolecules. Chem Commun. 1997;16:1577–1578.
   Web of Science ®Google Scholar
• Deschenaux R, Monnet F, Serrano E, Turpin F, Levelut AM. Columnar phases from covalent and hydrogen-bonded liquid-crystalline ferrocene derivatives. Helv Chim Acta. 1998;81:2072–2077.
   Web of Science ®Google Scholar
• Massiot P, Imperor-Clerc M, Veber M, Deschenaux R. Supramolecular metallomesogens: hydrogen-bonded ferrocene-containing liquid crystals which display bicontinuous cubic phases. Chem Mater. 2005;17:1946–1951.
   Web of Science ®Google Scholar
• Majumdar KC, Shyam PK, Rao, DSS, Prasad K. Oxadiazole-based non-symmetric liquid crystalline trimers terminating with ferrocene and cholesterol units exhibiting TGBC* phase over a wide thermal range. Liq Cryst. 2012;39:1117–1123.
   Web of Science ®Google Scholar
• Majumdar KC, Ghosh T, Shyam PK. Ferrocene-based novel calamitic metallomesogens containing a 2-phenylbenzoxazole unit: synthesis and characterization. Liq Cryst. 2011;38:567–573.
   Web of Science ®Google Scholar
• Kawamoto H. The history of liquid-crystal displays. Proc IEEE. 2002;90:460–500.
   Web of Science ®Google Scholar
• Nakamura N, Kagawa S. Synthesis and physical properties of ferrocene derivatives (XXV) liquid crystallinity of 1,3-disubstituted ferrocene derivatives. Mol Cryst Liq Cryst. 2011;549:150–159.
   Web of Science ®Google Scholar
• Imrie C, Loubser C. A liquid crystalline ferrocene derivative with a chiral smectic c phase. J Chem Soc Chem Commun. 1994;18:2159–2160.
   Google Scholar
• Andersch J, Diele S, Tschierske C. Ferrocene-containing thermotropic liquid crystals: laterally connected twins. J Mater Chem. 1996;6:1465–1468.
   Web of Science ®Google Scholar
• Cook MJ, Cooke G, Fini AJ. A liquid crystalline ferrocenyl-phthalocyanine. J Chem Soc Chem Commun. 1995;17:1715–1716.
   Google Scholar
• Kadkin ON, Galyametdinov YG. Ferrocene containing liquid crystals. Russ Chem Rev. 2012;81:675–699.
   Web of Science ®Google Scholar
• Loubser C, Imrie C. Thermal properties of monosubstituted ferrocene derivatives: a series of new ferrocenomesogens. J Chem Soc Perkin Trans 2. 1997;3:399–410.
   Google Scholar
• Seshadri T, Haupt HJ. Thermotropic properties of monosubstituted ferrocene derivatives bearing bidentate N-benzoyl-N′-arylthiourea ligands — novel building blocks for heterometallic liquid crystal systems. J Mater Chem. 1998;8:1345–1350.
   Web of Science ®Google Scholar
• Nakamura N, Hanasaki T, Onoi H, Oida T. Syntheses and physical properties of ferrocene derivatives (IV) a study on the smectic structure of ferrocene derivatives containing a cholesteryl group. Mol Cryst Liq Cryst. 1994;257:43–48.
   Web of Science ®Google Scholar
• Makarov MV, Lemenovskii DA, Bruce AE, Bruce MRM, Dyadchenko VP. Thermotropic liquid crystals based on ferrocenylbiphenyl and ferrocenylterphenyl. Liq Cryst. 2006;33:485–494.
   Web of Science ®Google Scholar
• Nakamura N, Ishimizu M, Nishikawa M, Dogen N. Synthesis and physical properties of ferrocene derivatives (XXII): monosubstituted ferrocene derivatives containing biphenyl group in the mesogenic one. Mol Cryst Liq Cryst. 2010;516:114–121.
   Web of Science ®Google Scholar
• Nakamura N, Hiro K, Nishikawa M, Okabe T, Uno K. Synthesis and physical properties of ferrocene derivatives (XXIII) phase transition and unique molecular structure of monosubstituted ferrocene derivatives. Mol Cryst Liq Cryst. 2010;516:122–131.
   Web of Science ®Google Scholar
• Imrie C, Engelbrecht P, Loubser C, McCleland CW. Monosubstituted thermotropic ferrocenomesogens: an overview 1976–1999. Appl Organomet Chem. 2001;15:1–15.
   Web of Science ®Google Scholar
• Carlescu I, Scutaru AM, Apreutesei D, Alupei V, Scutaru D. The liquid crystalline behaviour of ferrocene derivatives containing azo and imine linking groups. Liq Cryst. 2007;34:775–785.
   Web of Science ®Google Scholar
• Kim SY, Kadkin ON, Kim EH, Choi MG. Phase behavior of some mono-substituted ferrocene- and [3]ferrocenophane-containing nematics with the cyclohexane ring in the rigid core. J Organomet Chem. 2011;696:2429–2437.
   Web of Science ®Google Scholar
• Carlescu I, Scutaru D, Hurduc N, Catanescu, O, Chien L-C. Monosubstituted ferrocene-containing liquid crystals. Mol Cryst Liq Cryst. 2005;439:107–123.
   Web of Science ®Google Scholar
• Carlescu I, Scutaru AM, Apreutesei D, Alupei V, Scutaru D. The liquid crystalline properties of some ferrocene-containing Schiff bases. Appl Organomet Chem. 2007;21:661–669.
   Web of Science ®Google Scholar
• Tsutomu I. (Mitsui Toatsu Chemicals), Naphthalene compound, and liquid crystal composition and liquid crystal element using the same. EP0757032A2. 1997.
   Google Scholar
• Kuo HM. Li SY, Sheu HS, Lai CK. Symmetrical mesogenic 2, 5-bis (6-naphthalen-2-yl)-1,3, 4-thiadiazoles. Tetrahedron. 2012;68:7331–7337.
   Web of Science ®Google Scholar
• Bruce DW, Dunmer DA, Lalinde E, Maitlis PM, Styring P. Novel transition metal-containing nematic and smectic liquid crystals. Chem Commun. 1986;8:581–582.
   Google Scholar
• Marcos M, Ros MB, Seranno JL, Esteruelas MA, Sola E, Oro L, Barbera AJ. Liquid-crystal behavior in ionic complexes of silver(I): molecular structure-mesogenic activity relationship. Chem Mater. 1990;2:748–758.
   Web of Science ®Google Scholar
• Bruce DW, Dunmer DA, Maitlis PM, Esteruelas MA, Hunt SE, Lagadec RL, Marsden JR, Sola E, Stacey JM. Synthesis and mesomorphism of stilbazole complexes of rhodium(I) and iridium(I). J Mater Chem. 1991;1:251–254.
   Web of Science ®Google Scholar
• Campillos E, Marcos M, Serrano JL, Alonso PJ. Paramagnetic rod-like liquid crystals, bis[5-(4-alkoxybenzoyloxy) salicylaldehyde] copper (II). J Mater Chem. 1991;1:197–199.
   Web of Science ®Google Scholar
• Kaharu T, Tanaka T, Sawada M, Takahashi SJ. Liquid-crystalline palladium– and platinum–isonitrile complexes: synthesis, mesomorphic properties and molecular structure. Mater Chem. 1994;4:859–865.
   Web of Science ®Google Scholar
• Gray GW, Hartley JB, Jones B. Mesomorphism and chemical constitution. Part V. The mesomorphic properties of the 4′-n-alkoxydiphenyl-4-carboxylic acids and their simple alkyl esters. J Chem Soc. 1955;1412–1420.
   Web of Science ®Google Scholar
• Imrie C, Loubser C, Engelbrecht P, McCleland C, Zheng Y. The synthesis and liquid crystal behaviour of monosubstituted ferrocenomesogens. J Organomet Chem. 2003;665:48–64.
   Web of Science ®Google Scholar
• Makarov MV, Kuleshova LN, Hofmann DWM, DyadChenko VP, Antipin MY. Ferrocenylbiphenylyl- and ferrocenylterphenylyl-containing liquid crystals: solid-phase precursors, structure, and properties. Crystallogr Rep. 2006;51:792–803.
   Web of Science ®Google Scholar
• Apreutesei D, Lisa G, Scutaru D, Hurduc N. Investigation on thermal stability of some ferrocene liquid crystals bearing azo, ferrocenyl and cholesteryl units. J Optoelectron Adv Mater. 2006;8:737–740.
   Web of Science ®Google Scholar
• Lisa G, Wilson DA, Scutaru D, Tudorachi N, Hurduc N. Investigation of thermal degradation of some ferrocene liquid crystals. Thermochim Acta. 2010;507:49–59.
   Web of Science ®Google Scholar
• Bernstein J. Conformational polymorphism. In: Desiraju GR, editor. Organic solid state chemistry. Amsterdam: Elsevier; 1987. p. 471–518.
   Google Scholar
• Imrie CT. Laterally substituted dimeric liquid crystals. Liq Cryst. 1989;6:391–396.
   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. 1189;6:1–10.
   Google Scholar
• Donaldson T, Staesche H, Lu ZB, Handerson PA, Achard MF, Imrie CT. Symmetric and non-symmetric chiral liquid crystal dimers. Liq Cryst. 2010;37:1097–1110.
   Web of Science ®Google Scholar
• Gray GW, Jones B. The preparation of 4- and 5-n-alkoxy-1-naphthoic and 6- and 7-n-alkoxy-2-naphthoic acids. J Chem Soc. 1954;678–683.
   Web of Science ®Google Scholar