π-Extended tetrathiafulvalene BODIPY (ex-TTF-BODIPY): a redox switched on-off-on'' electrochromic system with two near-infrared fluorescent outputs

A pi-extended tetrathiafulvalene-boradiazaindacene chimera, ex-TTF-BODIPY, has been prepared. The resulting system undergoes sequential one-electron oxidations, allowing access to both the mono-oxidized radical cationic and dicationic states. Additionally, ex-TTF-BODIPY displays electrochromic and electrofluorochromic behaviour in the near-IR portion of the electromagnetic spectrum and functions as a redox switched on-off-on'' emissive system.