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2015 | 13 | 1 |
Tytuł artykułu

Synthesis, Photo-sensitive and Electrochemical Properties of Rod-like Aromatic Aldehyde with Azo Bridge

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Eight new rod-like liquid crystal molecules composed by a long rigid core of three six-member rings (cyclohexane ring or benzene ring), azo, ester and terminal aldehyde groups have been prepared. These rod-like liquid crystalline molecules were designed to construct new structures to further study photo-isomerization in their mesophases. All the compounds have been characterized based on their basic spectral data, differential scanning calorimeter (DSC) and hot stage polarizing optical microscope (HS-POM). The result showed that all the molecules, even those with the shortest terminal methyl group, have liquid crystalline properties. Their mesophases are nematic within the temperature ranges from 85 to 145°C. They exhibit photo-sensitivities not only in methanol solutions but also in a mesophase when exposed to UV light. The highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) and the differences between the frontier molecular orbitals (Eg) of these compounds were determined by cyclic voltammetry. The effect of even-odd carbon number of the terminal straight alkyl chain on the UV spectral data and the Eg were observed. The difference between the Eg of these compounds are in excellent agreement with the difference of their maximum absorption wavelength in UV spectra.

Opis fizyczny
  • School of Chemistry and Chemical Engineering, Xianyang Normal University, Shaanxi, China
  • School of Chemistry and Chemical Engineering, Xianyang Normal University, Shaanxi, China
  • School of Chemistry and Chemical Engineering, Xianyang Normal University, Shaanxi, China
  • [1] An Z.W., Zheng M.Y., Wei Y.S., Li, J.L., TEMPO containing esters and their magnetic and liquid crystal properties, Mol. Cryst. Liq. Cryst., 2012, 557, 28-38[WoS]
  • [2] Kilincarslan R., Erdem E., Synthesis and spectral characterization of some new azo dyes and their metal complexes, Transition Met. Chem., 2007, 32, 102-106
  • [3] Dabbagh H.A., Teimouri A., Insertion reaction of azidosulfonyl azo dye with model alicyclic and heterocyclic compounds, Russ. J. Org. Chem., 2008, 44, 1464–1470[WoS]
  • [4] Kashanian S., Zeidali S.H., Omidfar K., Shahabadi N., Multi-spectroscopic DNA interaction studies of sunset yellow food additive, Mol Biol Rep., 2012, 39, 10045-10050[WoS][Crossref]
  • [5] Singh A.K., Das J., Majumdar N., Novel bacteriorhodopsin analogs based on azo chromophores, J. Am. Chem. Soc., 1996, 118, 6185-6191
  • [6] Nieto G., Huvaere K., Skibsted L.H., Antioxidant activity of rosemary and thyme by-products and synergism with added antioxidant in a liposome system, Eur Food Res Technol., 2011, 233, 11-18[WoS]
  • [7] Nagaveni N.G., Royb A., Prasad V., Achiral bent-core azo compounds: effect of different types of linkage groups and their direction of linking on liquid crystalline properties, J. Mater. Chem., 2012, 22, 8948-8959[Crossref][WoS]
  • [8] Kay E.R., Leigh D.A., Zerbetto F., Synthetic molecular motors and mechanical machines, Angew. Chem., 2007, 119, 72-196[Crossref][WoS]
  • [9] Balzani V., Credi A., Venturi M., Light powered molecular machines, Chem. Soc. Rew., 2009, 38, 1542-1550
  • [10] Silva A.P.D., Gunarane H.Q.N., Rice T.E., Signaling recognition events with fluorescent sensors and switches, Chem. Rev., 1997, 97, 1515-1566
  • [11] Ledoux I., Zyss J., Barni E., Barolo C., Diulgheroff N., Quagliotto P., Viscardi G., Properties of novel azodyes containing powerful acceptor groups and thiophene moiety, Synth. Met., 2000, 115, 213–217
  • [12] Urbas A., Tondiglia V., Natarajan L., Sutherland R., Yu H., Li J.H., et al. Optically switchable liquid crystal photonic structures, J. Am. Chem. Soc., 2004, 126, 13580-13581
  • [13] Newton J., Walton H., Coles H., Hodge P., New LMM organosiloxanes with photoisomerising azo groups, Mol. Cryst. Liq. Cryst., 1995, 260, 107-125
  • [14] Furumi S., Akiyama H., Morino S., Ichimura K., A convenient preparation of photoactive monolayers for liquid crystal photoalignment by the surface adsorption of an aminoalkylated, J. Mater. Chem., 1998, 8, 65-70[Crossref]
  • [15] Wang J.H., Liu L., Liu G.F., Guo J.X., Jia D.Z., Properties of novel azodyes containing powerful acceptor groups and thiophene moiety, Synth. Met., 2000, 115, 213±217
  • [16] Zhang Y.Q., Ortega J., Baumeister U., Folcia C. L., Sanz-Enguita G., Walker C., et al., Activated carbon modified with 4-(8-hydroxyquinoline-azo)benzamidine for selective solid-phase extraction and preconcentration of trace lead from environmental samples, Microchim Acta, 2010, 171, 225-232[WoS]
  • [17] Nicolescu F.A., Jerca V.V., Dancus I., Petris A., Nicolescu T.V., Rau I.B., et al. Synthesis and characterization of side-chain maleimide-styrene copolymers with new pendant azobenzene moieties, J. Polym. Res., 2011, 18, 1009-1016[WoS][Crossref]
  • [18] Liu J.Q., Zhang Q.Z., Zhang J.Z., Hou, W.G., Photochemical behaviours of star-like liquid crystal with azobenzene terminal groups, J. Mater. Sci., 2005, 40, 4517-4521[Crossref]
  • [19] Wang J.H., Liu L., Liu G.F., Guo J.X., Jia D.Z., Three novel photoisomeric compounds of the 4-acyl pyrazolone derivants: Crystal structures and substituent effects on photo-isomerism in solid state, Sci. Chin. Ser. B: Chem., 2008, 51, 661-668
  • [20] Kašpar M., Novotná V., Hamplová V., Podoliak N., Nonnenmacher D., Glogarová F., et al., Antiferroelectric phase in liquid crystalline compounds containing an azo groups containing an azo group in their molecular core, Liquid crystal, 2011, 38, 309-315
  • [21] Zheng M.Y., An Z.W., Synthesis and mesophase of liquid crystals of multi-ring monoesteryl aryl aldehyde, Chin. J. Appl. Chem., 2007, 24, 396-400, (in Chinese)
  • [22] Chouhary V.R., Dumbre D.K., Narkhede V.S., Solvent-free oxidation of aldehydes to acids by TBHP using environmental-friendly MnO4-1 4 -exchanged Mg-Al hydrotalcite catalyst, J. Chem. Sci., 2012, 124, 835-839
  • [23] Zheng M.Y., An Z.W., Rod-like Schiff Base Magnetic Liquid Crystals Bearing Organic Radical, Chin. J. Chem., 2006, 24, 1754-1757[Crossref]
  • [24] Zou Z.Q., Deng Z.J., Yu X.H., Zhang M.M., Zhao S.H., Luo T., et al. A new facile approach to N-alkylpyrroles from direct redox reaction of 4-hydroxy-L-proline with aldehydes, Sci. Chin. Ser. B: Chem., 2012, 55, 43-49[Crossref]
  • [25] Kuvshinova S.A., Burmistrov V.A., Fokin D.S., Blokhina S.V., Koifman O.I., Thermodynamic Properties and Selectivity of Substituted Liquid-Crystal Formylazobenzenes as Stationary Phases for Gas Chromatography, Anal. Chem., 2009, 64, 505-508[WoS]
  • [26] Arias J., Bardaji M., Espinet P., Folcia C.L., Ortega, J., Etxebarria, J. Azo isocyanide gold(I) liquid crystals, highly birefringent and photosensitive in the mesophase, Inorg. Chem., 2009, 48, 6205-6210[WoS]
  • [27] Xiang N.J., Lee T.H., Leung L.M., So S.K., Shi J.X., Gong M.L., Synthesis and photoluminescence of two novel bipolar organic compounds, Acta Chimica Sinica, 2006, 64, 1157-1162, (in Chinese)
  • [28] Pandey S., Kolli B., Mishra S.P., Samui A.B.S., Siloxane polymers containing azo moieties synthesized by click, J. Polym. Sci. Part A: Polym. Chem., 2012, 50, 1205-1215 [Crossref]
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