Synthesis and Characterization of Poly(imino alcohol/quinone) Precursor

1,4-Bis(4′-bromobenzoyl)benzene(1) was synthesized using a modified method.1,4′-bis(4′-anilinobenzoyl)benzene(2) was synthesized by a palladium-catalyzed amination of 1,4-bis(4′-bromobenzoyl)benzene(1) with aniline as a primary aromatic amine using NaOt-Bu as a base and BINAP as a ligand.Both of the two carbonyl groups of 1,4-bis(4-anilinobenzoyl)benzene(2) were attacked by phenyllithium as a carbanion with a high nucleophilicity to afford 1,4′-bis{(phenyl-(4-anilinophenyl)methanol)}benzene(3) in 93% yield.Di-tertiary alcohol 1,4′-bis{(phenyl-(4-anilinophenyl)methanol)}benzene(3) forms 1,4-bis{(4-benzylidene-cyclohexa-2,5-dienylidene)-anilino}benzene(4) in an elimination reaction.The resulting compound(4) was extracted to a deeply purple solution using chloroform.The solution was washed with water,evaporated,and dried in vacuum,with a yield as purple powders.