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We report the synthesis of donor–acceptor–donor triads based on the indeno[1,2-b]fluorene-6,12-dione (IF) scaffold. Arylethynyl donor group attachment expands the light absorption of these molecules to the 600–700 nm region compared to derivatives with nondonating silylethynyl substituents yet does not affect the electron-accepting capabilities of the IF core. All triads show reduction potentials at similar or less negative potentials compared to the silylethynyl derivatives. Protonation studies using the bis(dibutylanilino) triad verify the charge transfer nature of the expanded absorption profile.