-region O-annulation of arylene diimide enables ambipolar transport of a polycyclic aromatic hydrocarbon with strong NIR absorption.

While the heteroannulation of arylene diimides serves as a powerful approach for designing new π-functional materials, most of the heteroannulated arylene diimides are constructed based on π-extension at their -areas or -directions. Herein, based on a -region O-annulation strategy, a novel O-doped polyaromatic hydrocarbon O-ADA was successfully prepared, showing not only ambipolar charge transport with improved charge mobilities, but also much red-shifted NIR absorption profiles and thus yielding enhanced photothermal conversion efficiencies upon light irradiation as compared to its parent ADA compound.