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.