In Situ Synthesis of Hexakis(alkoxy)diquinoxalino[2,3-a:2‘,3‘-c]phenazines: Mesogenic Phase Transition of the Electron-Deficient Discotic Compounds
- 1 April 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (9) , 3181-3185
- https://doi.org/10.1021/jo035840l
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.Keywords
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