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

Abstract

Two novel anionic conjugated copolyelectrolytes PSDPPPV and PSDPPPE were synthesized via Heck/Sonogashira coupling reactions and characterized by FT-IR, 1 H NMR, UV-vis, and PL spectroscopy. The two polymers are respectively constituted of 2,5-diethoxy-1,4-phenyleneethynylene (DPV) and 2,5-di ethoxy-1,4-phenyleneethynylene (DPE) with 1,4-diketo-2,5-bis (4-sulfonylbutyl)-3,6-diphenylpyrrolo[3,4-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 non-ionic 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.

Novel isoindigo-based conjugated polyelectrolytes: Synthesis and fluorescence quenching behavior with water-soluble poly(p -phenylenevinylene)s

“…The polymers were collected by filtration after precipitating in the mixed solvent (ethanol/ethyl ether = 1/1 and ethyl ether/acetone = 5/4), respectively, and purified by dialyzed against deionized water. The methods are similar to the polymerization of DPP‐based CPEs reported in our previous work . Water solubility of (+)‐PIDPV, (−)‐PIDPV, (+)‐PPV and (−)‐PPV are around 11.8 mg mL −1 ([repeat unit]=1.21 × 10 −2 M), 12.5 mg mL −1 ([repeat unit] = 1.42 × 10 −2 M), 120.7 mg mL −1 ([repeat unit] = 0.132 M) and 115.2 mg mL −1 ([repeat unit] = 0.159 M) at room temperature, respectively.…”

“…While the impurities mentioned above are hardly to be removed thoroughly by filtration and recrystallization from common organic solvents. Therefore, pure monomer 1 was successfully obtained by recrystallization from potassium chloride aqueous solution as same as the purification method of water‐soluble DPP derivative reported in our previous work . Monomer 4 was prepared via a five‐step reaction, containing Williamson ether reaction, chloromethylation, Ylide reaction, Wittig reaction, and quaternization.…”

“…The ionic hydrogen bond dyes as water‐soluble 1,4‐diketopyrrolo[3,4‐c]pyrrole (DPP) derivatives have been obtained by modified with carboxyl or sulfuric acid ester on its N ‐alkyl side chain, but it gives a low yield and an unsatisfied purity. Recently, the strategy to transform such hydrogen‐bond dyes as quinacridone and DPP into water‐soluble derivatives with high yield and purity has been realized by alkylation with sultone, which makes it possible to synthesize water‐soluble ID derivatives. And the sulfonated ID electrolytes must be important parts in the synthesis of anionic ID‐based conjugated polyelectrolytes.…”

Novel benzimidazole-based conjugated polyelectrolytes: synthesis, solution photophysics and fluorescent sensing of metal ions

“…In water, (+)-PPBIPV aggregates strongly by π-π stacking as same as other conjugated polyelectrolytes (34), which means that the conjugated layers of the polyelectrolytes are stacked mutually. This aggregation causes the conjugated polyelectrolytes to reach a higher degree of conjugation, making it easier for excitons to transfer between the backbones (35). Thus, the fluorescence quenching of (+)-PPBIPV in water may be attributed to energy dissipation caused by excitons transfer.…”

Cationic Main‐Chain Polyelectrolytes with Pyridinium‐Based p‐Phenylenevinylene Units and Their Aggregation‐Induced Gelation

“…Side‐ or main‐chain polyelectrolytes that contain charged, π‐conjugated repeat units are an interesting class of materials for potential applications in chemo‐ or biosensing as well as optoelectronic devices such as solar cells or organic light emitting diodes . In recent years, side‐chain conjugated polyelectrolytes based on several backbone motifs were developed including polyfluorenes, fluorene–benzothiazole copolymers, polythiophenes, poly‐ p ‐phenylenevinylenes, poly‐ p ‐phenyleneethynylenes among others for applications in sensing, imaging, as well as for enzyme activity, and charge transport studies . Fully conjugated poly(pyridinium salt)s, or polyelectrolytes containing viologen, as well as diethynylpyridinium units as main‐chain polyelectrolytes have been synthesized mainly for biosensing and optoelectronic applications.…”