Liquid crystalline analogues of curcumin

References

• Anand P, Thomas SG, Kunnumakkara AB, Sundaram C, Harikumar KB, Sung B, Tharakan ST, Misra K, Priyadarsini IK, Rajasekharan KN, Aggarwal BB. Biological activities of curcumin and its analogues (congeners) made by man and mother nature. Biochem Pharmacol. 2008;76:1590–1611. doi:10.1016/j.bcp.2008.08.008.
   PubMed Web of Science ®Google Scholar
• Barbera J, Cativiela C, Serrano JL, Zurbano MM. Mesogenic behaviour in some pyrazole and isoxazole derivatives. Liq Cryst. 1992;11:887–897. doi:10.1080/02678299208030692.
   Web of Science ®Google Scholar
• Pabon HIJ. A synthesis of curcumin and related compounds. Recuile des Travaux Chimiques des Pays-Bas. 1964;83:379–386.
   Google Scholar
• Seguel CG, Borchers B, Haase W, Aguilera C. Synthesis and thermotropic properties of new mesogenic pyrazole and isoxazole derivatives. Liq Cryst. 1992;11:899–903. doi:10.1080/02678299208030693.
   Web of Science ®Google Scholar
• Iglesias R, Serrano JL, Sierra T. FLCs with a five-membered ring in the mesogenic core. Liq Cryst. 1997;22:37–46. doi:10.1080/026782997209658.
   Web of Science ®Google Scholar
• Barbera J, Gimenez R, Serrano JL, Alcala R, Villacampa B, Villalba J, Ledoux I, Zyss J. β-Diketone, pyrazole and isoxazole derivatives with polar groups: liquid crystalline and non-linear optical properties. Liq Cryst. 1997;22:265–273. doi:10.1080/026782997209315.
   Web of Science ®Google Scholar
• Beltrán E, Cavero E, Barberá J, Serrano JL, Elduque A, Giménez R. Self-assembly in helical columnar mesophases and luminescence of chiral 1H-pyrazoles. Chem Eur J. 2009;15:9017–9023. doi:10.1002/chem.200901154.
   PubMed Web of Science ®Google Scholar
• Kuo HM, Tsai SL, Lee GH, Sheu HS, Lai CK. Heterocyclic 3,5-disubstituted phenylpyrazoles and isoxazoles: synthesis and mesomorphic behavior. Tetrahedron. 2013;69:618–626. doi:10.1016/j.tet.2012.11.013.
   Web of Science ®Google Scholar
• Chou SY, Chen CJ, Tsai SL, Sheu HS, Lee GH, Lai CK. Columnar metallomesogens derived from unsymmetrical pyrazoles. Tetrahedron. 2009;65:1130–1139. doi:10.1016/j.tet.2008.11.080.
   Web of Science ®Google Scholar
• Thaker BT, Solanki DB, Patel BS, Patel NB. Synthesis, characterization and liquid crystalline properties of some Schiff base and cinnamate central linkages involving 1,3,5-trisubstituted pyrazolone ring system and their Cu(II) complexes. Liq Cryst. 2013;40:1296–1309. doi:10.1080/02678292.2013.804606.
   Web of Science ®Google Scholar
• Gallardo H, Conte G, Tuzimoto PA, Behramand B, Molin F, Eccher J, Bechtold IH. New luminescent liquid crystals based on 2,1,3-benzothiadiazole and bent five-membered N-heterocyclic cores. Liq Cryst. 2012;39:1099–1111. doi:10.1080/02678292.2012.698313.
   Web of Science ®Google Scholar
• Barberá J, Giménez R, Serrano JL. Mesogenic pyrazaboles: synthesis, properties, and structural characterization. Chem Mater. 2000;12:481–489. doi:10.1021/cm991120c.
   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
• Chen MC, Lee SC, Ho CC, Hu TS, Lee GH, Lai CK. Calamitic metallomesogens derived from unsymmetric pyrazoles. Tetrahedron. 2009;65:9460–9467. doi:10.1016/j.tet.2009.08.062.
   Web of Science ®Google Scholar
• Barberá J, Elduque A, Giménez R, Oro LA, Serrano JL. Pyrazolate “golden” rings: trinuclear complexes that form columnar mesophases at room temperature. Angew Chem Int Ed Engl. 1996;35:2832–2835. doi:10.1002/anie.199628321.
   Web of Science ®Google Scholar
• Barberá J, Elduque A, Giménez R, Lahoz FJ, López JA, Oro LA, Serrano JL. (Pyrazolato)gold complexes showing room-temperature columnar mesophases. Synthesis, properties, and structural characterization. Inorg Chem. 1998;37:2960–2967. doi:10.1021/ic971632y.
   Web of Science ®Google Scholar
• Kishikawa K, Harris MC, Swager TM. Nematic liquid crystals with bent-rod shapes: mesomorphic thiophenes with lateral dipole moments. Chem Mater. 1999;11:867–871. doi:10.1021/cm980631g.
   Web of Science ®Google Scholar
• Levitsky IA, Kishikawa K, Eichhorn SH, Swager TM. 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
• Imrie CT. Laterally substituted dimeric liquid crystals. Liq Cryst. 1989;6:391–396. doi:10.1080/02678298908034184.
   Web of Science ®Google Scholar
• King ST. Low-temperature matrix isolation study of hydrogen-bonded. High boiling organic compounds. I. The sampling device and the infrared spectra of pyrazole, imidazole, and dimethyl phosphinic acid. J Phys Chem. 1970;74:2133–2139.
   Web of Science ®Google Scholar
• Castaneda JT, Denisov GS, Kucherov Yu S, Schreiber VM, Shurukhina AV. Infrared and ab initio studies of hydrogen bonding and proton transfer in the complexes formed by pyrazoles. J Mol Struct. 2003;660:25–40. doi:10.1016/j.molstruc.2003.07.010.
   Web of Science ®Google Scholar
• Rice CA, Borho N, Suhm MA. Dimerization of pyrazole in slit jet expansions. Zeitschrift für Physikalische Chemie. 2005;219:379–388. doi:10.1524/zpch.219.3.379.59183.
   Web of Science ®Google Scholar
• Morale F, Date RW, Guillon D, Bruce DW, Finn RL, Wilson C, Blake AJ, Schröder M, Donnio B. Columnar mesomorphism from hemi-disc-like metallomesogens derived from 2,6-bis[3′,4′,5′-tri(alkoxy)phenyliminomethyl]pyridines (L): crystal and molecular structures of [M(L)Cl2] (M = Mn, Ni, Zn). Chem Eur J. 2003;9:2484–2501. doi:10.1002/chem.200204578.
   PubMed Web of Science ®Google Scholar
• Donnio B, Heinrich B, Allouchi H, Kain J, Diele S, Guillon D, Bruce DW. A generalized model for the molecular arrangement in the columnar mesophases of polycatenar mesogens. Crystal and molecular structure of two hexacatenar mesogens. J Am Chem Soc. 2004;126:15258–15268. doi:10.1021/ja0471673.
   PubMed Web of Science ®Google Scholar
• Marcos M, Gimenez R, Serrano JL, Donnio B, Heinrich B, Guillon D. Dendromesogens: liquid crystal organizations of poly(amidoamine) dendrimers versus starburst structures. Chemistry. 2001;7:1006–1013. doi:10.1002/1521-3765(20010302)7:5<1006::AID-CHEM1006>3.0.CO;2-N.
   PubMed Web of Science ®Google Scholar
• Attias AJ, Cavalli C, Donnio B, Guillon D, Hapiot P, Malthête J. Columnar mesophase from a new disclike mesogen based on a 3,5-dicyano-2,4,6-tristyrylpyridine core. Chem Mater. 2002;14:375–384. doi:10.1021/cm010725h.
   Web of Science ®Google Scholar
• Donnio B, Bruce DW. Liquid-crystalline complexes of palladium (II) and platinum (II) with di- and tri-alkoxystilbazoles: ligand control of mesomorphism. J Chem Soc Dalton Trans. 1997;2745–2756. doi:10.1039/a702756g .
   Google Scholar
• Plasseraud L, Cuervo LG, Guillon D, Suess-Fink G, Deschenaux R, Bruce DW, Donnio B. Hexacatenar liquid-crystalline complexes of palladium (II) and platinum (II) based on trialkoxystilbazole esters. J Mater Chem. 2002;12:2653–2658. doi:10.1039/b203889g.
   Web of Science ®Google Scholar
• Rowe KE, Bruce DW. The synthesis and mesomorphism of di-, tetra – and hexa-catenar liquid crystals based on 2,2′-bipyridine. J Mater Chem. 1998;8:331–341. doi:10.1039/a706400d.
   Web of Science ®Google Scholar