Vinylene-linked diketopyrrolopyrrole chromophores for electrochromism.

We report a novel series of vinylene-linked DPP compounds (1-5) formed via Knoevenagel condensation of dimethyl DPP (6) with various aromatic aldehydes. Incorporating the vinylene linkage and photo- and electro-active groups offered the distinct advantage of extending π-delocalization, resulting in deep-coloured solids with absorption maxima extending to 620-680 nm and low redox potentials. The DPP-triphenylamine compound (5) showed electrochromism in the near-infrared region. The colour of the solution changed from blue to green, and the absorption from 680 nm to 740 nm, leading to NIR-to-NIR absorption switching. This system exhibits rapid switching, swift response times (1.4 s and 1.2 s), and reversibility in electrochromic behaviour.