Synthesis and surfactochromicity of 1,4‐diketopyrrolo[3,4‐c]pyrrole(DPP)‐based anionic conjugated polyelectrolytes

Two novel anionic conjugated copolyelectrolytes PSDPPPV and PSDPPPE were synthesized via Heck/Sonogashira coupling reactions and characterized by FT‐IR, ¹H NMR, UV‐vis, and PL spectroscopy. The two polymers are respectively constituted of 2,5‐diethoxy‐1,4‐phenyleneethynylene (DPV) and 2,5‐diethoxy‐1,4‐phenyleneethynylene (DPE) with 1,4‐diketo‐2,5‐bis(4‐sulfonylbutyl)‐3,6‐diphenylpyrrolo3,4‐c]pyrrole (SDPP) which is a novel water soluble diketopyrrolopyrrole derivative. PSDPPPV and PSDPPPE show broad absorption band in visible region and they exhibit strong fluorescence quenching in aqueous solution. The fluorescence of their aqueous solutions can be enhanced in the presence of cationic surfactant or polymer nonionic surfactant. Fluorescence enhancement by introduction of polyvinylpyrrolidone (PVP) shows linear response. This result provides a controllable method to increase fluorescence intensity of dipyrrolopyrrole‐based conjugate polyelectrolytes in aqueous phase. The optical properties suggested that PSDPPPV and PSDPPPE which are negatively charged conjugated polymers can assemble with positively charged photovoltaic materials to form ionic photoactive layer. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 739–751