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Synthesis and Liquid Crystalline Properties of Some [3]Ferrocenophane-containing Schiff’s Bases and â-Enaminoketone

Oleg N Kadkin ,Yuri G Galyametdinov
Yonsei University, Seoul, South Korea Kazan State Technological University, Kazan, Russia
A novel series of mono-substituted [3ferrocenophane-containing Schiff’s bases was synthesized by condensing the isomeric 3- and 2- p-aminophenyl[3]ferrocenophanes with aldehydes of the common formulas p-C12H25O(C6H4)COO(C6H3)(X)CHO and p-C12H25O-(C6H3)(X)-CHO, (X=H or OH). Condensation of these aldehydes with the disubstituted isomers, 3,4-di- and 3,4’-bis- p-aminophenyl[3ferrocenophanes, yielded an another series of [3]ferrocenophane-containing azomethines. Besides, a â-enaminoketone derived from the 3-(p-aminophenyl)[3]ferrocenophane and p-C12H25O-(C6H4)-(CO)-CH2-CHO was prepared. Structures of the synthesized compounds were determined by means of mass, IR, UV, and 1H NMR spectroscopies. Mono-substituted derivatives obtained from the 3-aminophenyl[3]ferocenophane and p-C12H25O(C6H4)COO(C6H3)(X)CHO (X=H or OH) exhibited thermotropic mesomorphism of the nematic type identified by characteristic schliren textures under a polarizing optical microscope. The 3,4-disubstituted [3]ferrocenophane imines are non-mesogenic, while their isomeric 3,4’-bis-substituted analogues showed smectogenic properties. The [3]ferrocenophane-containing â-enaminoketone showed complex mesomorphic behavior apparently connected with occurrence of the keto-enamine and imino-enol tautomeric equilibrium in this compound.

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