Synthesis of wholly aromatic polyketones containing optically active macrocycles

Abstract

Wholly aromatic polyketones 7 containing bisbinaphthyl macrocycles were synthesized via P2O5-MsOH mediated direct condensation reaction of compound 3 with chlorobenzoic acids 4, nucleophilic aromatic substitution reaction of the resulting binaphthyl (5) with (S)-BINOL (1) in DMF/toluene, and NiBr2/Zn mediated aromatic coupling polymerization. The resulting polyketones 7 have excellent thermal resistance and solubility to organic solvents. Cyclic monomers 6 and polymers 7 have higher molar rotations based on optically active cyclic structures than pre-cyclized compounds 5. © 2007 The Society of Polymer Science.