Modulation of Chiroptical Properties in a Series of Helicene-like Compounds.

ABSTRACT

We describe a large-scale synthesis of a series of helicene-like compounds based on a dibenzo[c]acridine fragment by the Friedlander reaction. The series includes targeted constrained (closed) derivatives comprising 11 rings that exhibit very intense circularly polarized luminescence (CPL) (glum = 8 × 10-3) contrary to their nonconstrained (open) 10-ring precursors that are not CPL active. The relationship between structure and chiroptical properties in the series is discussed with the aid of quantum-chemical calculations.