A novel, highly soluble chromophore for use in organic electronics based on an indigoid structure is reported. Copolymerization with thiophene affords an extremely narrow band gap polymer with a maximum absorption at 鈭?00 nm. The novel polymer exhibits high crystallinity and high ambipolar transport in OFET devices of 0.23 cm2 V鈥? s鈥? for holes and 0.48 cm2 V鈥? s鈥? for electrons. OPV device efficiencies up to 2.35% with light absorbance up to 950 nm demonstrate the potential for this novel chromophore in near-IR photovoltaics.