Buchwald-Hartwig Coupling at the Naphthalenediimide Core: Access to Dendritic, Panchromatic NIR Absorbers with Exceptionally Low Band Gap.

The first successful Buchwald-Hartwig reaction at the naphthalenediimide core is reported, leading to the coupling of diverse secondary aromatic amines including dendritic donors. The G1-dendrimer-based donor exhibit blackish color, providing access to black absorbing systems. λonset values up to 1070 nm was achieved, which is the maximum from a single NDI scaffold. These dyes also manifest multielectron reservoir properties. A total of eight-redox states with a band gap of ∼0.95 eV was accomplished.