Preparation of Soluble Polypyrrole with -C≡C-p-C6H4-hexyl Side Chains at the N-Position and Its Self-assembling Behavior

Yamashita, Risako; Koizumi, Toru; Sasaki, Shintaro; Yamamoto, Takakazu

doi:10.1295/polymj.pj2007083

Cited by 8 publications

(4 citation statements)

References 19 publications

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“…Additionally, polymerizations in which the alkyne remains intact have been reported. Yamamoto published the co-polymerization of N -alkynyl pyrroles 304a,b with the di(stanyl)thiophenes 305a,b (Scheme 80, Reaction (3) [128,129,130]). Yamamoto also reported the oxidative polymerization of 307 with TBAPF 6 in 2012 (Scheme 80, Reaction (4) [131]).…”

Section: Applications Of N-alkynyl Azolesmentioning

confidence: 99%

Preparation and Utility of N-Alkynyl Azoles in Synthesis

Reinus

Kerwin

2019

Molecules

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Heteroatom-substituted alkynes have attracted a significant amount of interest in the synthetic community due to the polarized nature of these alkynes and their utility in a wide range of reactions. One specific class of heteroatom-substituted alkynes combines this utility with the presence of an azole moiety. These N-alkynyl azoles have been known for nearly 50 years, but recently there has been a tremendous increase in the number of reports detailing the synthesis and utility of this class of compound. While much of the chemistry of N-alkynyl azoles mirrors that of the more extensively studied N-alkynyl amides (ynamides), there are notable exceptions. In addition, as azoles are extremely common in natural products and pharmaceuticals, these N-alkynyl azoles have high potential for accessing biologically important compounds. In this review, the literature reports of N-alkynyl azole synthesis, reactions, and uses have been assembled. Collectively, these reports demonstrate the growth in this area and the promise of exploiting N-alkynyl azoles in synthesis.

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Section: Applications Of N-alkynyl Azolesmentioning

confidence: 99%

Preparation and Utility of N-Alkynyl Azoles in Synthesis

Reinus

Kerwin

2019

Molecules

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“…11−13 Although PPy is an attractive polymeric material, PPy has been suffering from low processability, including poor solubility in general solvents, infusible character, and low mechanical strength, which has prevented PPy from making a prominent commercial impact. For improvement of the processability of PPy, several strategies have been proposed: (1) synthesis of PPy soluble in liquid media by introduction of bulky side chains to the backbone via the covalent bond 14 or of bulky dopant via electrostatic interactions; 15 (2) in situ polymerization from metastable mixtures of pyrrole (Py) monomers and oxidants that enable processability, initiated by solvent evaporation; 16 (3) combining of PPy with substrates with high processability; 17−19 and (4) synthesis in the form of colloidal particles in liquid media. 20−22 There have been a series of studies on the synthesis of the PPy in a form of colloidal particles.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Polypyrrole (PPy) is one of the fascinating conjugated organic polymers, which has grown to receive considerable interest for more than 100 years. − Owing to unique electrical, optical, and biocompatible properties and ease in synthesis, PPy has found its technological applications as electrodes, electronic devices, sensors, , actuators, biomaterials, − and light-to-heat conversion materials. − Although PPy is an attractive polymeric material, PPy has been suffering from low processability, including poor solubility in general solvents, infusible character, and low mechanical strength, which has prevented PPy from making a prominent commercial impact. For improvement of the processability of PPy, several strategies have been proposed: (1) synthesis of PPy soluble in liquid media by introduction of bulky side chains to the backbone via the covalent bond or of bulky dopant via electrostatic interactions; (2) in situ polymerization from metastable mixtures of pyrrole (Py) monomers and oxidants that enable processability, initiated by solvent evaporation; (3) combining of PPy with substrates with high processability; − and (4) synthesis in the form of colloidal particles in liquid media. − …”

Section: Introductionmentioning

confidence: 99%

Colloidally Stable Polypyrrole Nanoparticles Synthesized by Surfactant-Free Coupling Polymerization

Atsuta,

Takeuchi,

Shioda

et al. 2023

Langmuir

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Surfactant-free polypyrrole (PPy) nanoparticles, which were colloidally stable in aqueous medium, were successfully synthesized by coupling polymerization of pyrrole using Fe(NO 3 ) 3 solids in the absence of any colloidal stabilizer. The pyrrole monomers were gradually supplied from the vapor phase, and the coupling reaction of the monomers could proceed to generate PPy in a water medium. The resulting PPy nanoparticles were extensively characterized in terms of diameter, bulk chemical composition, surface chemistry, and colloidal stability by dynamic light scattering, electron microscopy, elemental microanalysis, Fourier transform infrared spectroscopy, Raman spectroscopy, electrophoresis, and X-ray photoelectron spectroscopy. The characterization results indicated that the PPy nanoparticles can be colloidally stable based on the electrostatic stabilization mechanism due to cationic charges generated on the PPy molecules by doping during the polymerization. General chemical oxidative polymerization in aqueous medium using the Fe(NO 3 ) 3 oxidant without a colloidal stabilizer as a control experiment resulted in generation of atypical PPy aggregates with over a micrometer size, indicating that the polymerization at low ionic strength is essential for colloidal particle formation. Finally, it was demonstrated that the PPy nanoparticles worked as a surfactant-free black-colored particulate emulsifier by adsorption at the oil−water interface to stabilize Pickering-type oil-in-water emulsions.

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“…In addition, organometallic polycondensations have recently been employed to obtain copolymers via a bis(trimethylstannyl)thiophene monomer and a dibromo pyrrole monomer. [31][32][33] However, the polymers obtained by the Stille polycondensation had a very low molecular weight. There was no report on preparing poly(thiophene-alt-pyrrole) via a single monomer which contains a metal functional group and a halogen group.…”

Section: Introductionmentioning

confidence: 99%