In Situ Synthesis of Hexakis(alkoxy)diquinoxalino[2,3-a:2‘,3‘-c]phenazines:  Mesogenic Phase Transition of the Electron-Deficient Discotic Compounds

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Title:	In Situ Synthesis of Hexakis(alkoxy)diquinoxalino[2,3-a:2‘,3‘-c]phenazines: Mesogenic Phase Transition of the Electron-Deficient Discotic Compounds
Authors:	徐秀福;Hsu, Hsiu-fu
Contributors:	淡江大學化學學系
Date:	2004-04-30
Issue Date:	2009-12-01
Publisher:	American Chemical Society
Abstract:	2,3,8,9,14,15-Hexakis(alkoxy)diquinoxalino[2,3-a:2‘,3‘-c]phenazines with alkyl side chains varying from 6 to 12 carbon atoms were readily synthesized by the condensation of hexaketocyclohexane with the respective 1,2-bisalkoxy-4,5-diaminobenzene. Polarization microscopy and DSC studies showed all these compounds to exhibit a very wide mesophase range of over 150 °C. An interesting Dhd to Drd transition was observed for the octyl derivative 3b, as determined by X-ray diffraction measurements. The hexyl derivative showed three reduction potentials, suggesting that the HATN core maintained its electron-deficient characteristic and considered suitable as an n-doped discotic-liquid crystalline material. Incorporation of six alkoxy chains did not override the electron deficiency of the HATN core.
Relation:	Journal of Organic Chemistry 69(9), pp.3181-3185
DOI:	10.1021/jo035840l
Appears in Collections:	[Graduate Institute & Department of Chemistry] Journal Article

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