Synthesis of Helical Aromatic Polyazomethines Consisting of Axially Dissymmetric Segments in the Main Chain

ABSTRACT Aromatic polyazomethines were prepared by the polycondensation of axially dissymmetric aromatic diamines and aromatic dialdehydes. The polycondensation of axially dissymmetric ( R )‐ or ( S )‐binaphthyl‐2,2′‐diamines and aromatic dialdehydes in DMF at 100°C afforded wholly aromatic polyazomethines ( M n = 4600–7600), which are soluble in common solvents such as tetrahydrofuran. The combination of ( R )‐ or ( S )‐6,6′‐diamino‐2,2′‐dimethylbiphenyls and aromatic dialdehydes also yielded soluble wholly aromatic polyazomethines ( M n = 5500–12,000). Computational studies showed that the stable conformations of the polymers have one‐handed helical structures. The chiroptical properties of the obtained polyazomethines were investigated based on circular dichroism (CD) spectra.