Polypyrrole from β-substituted pyrrole monomers

Casas, Raquel Brañas; Dicko, Amadou; Ribó, Josep M.; Vallès, Margarita; Ferrer-Anglada, N.; Bonnett, Raymond; Hanly, Noreen; Bloor, D.

doi:10.1016/0379-6779(90)90192-n

Cited by 22 publications

(5 citation statements)

References 12 publications

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“…In agreement with previous studies, [53,[55][56][57] the CV of 5 recorded in CH 2 Cl 2 containing TBAHSO 4 (0.1 m; Figure 4) revealed the characteristic irreversible wave of pyrrole oxidation at approximately 0.95 V. Owing to its limited conjugation pathway and lower number of electron-donating balkyl groups, the pyrrole-centered oxidation process is observed at a much more positive potential in 5 than in 4. This is very much as expected and is fully consistent with the failure to obtain cyclo [8]pyrrole from 5 through chemical oxidation; the required conditions simply appear too harsh.…”

Section: Resultssupporting

confidence: 91%

“…However, to the best of our knowledge, none of the investigations involving polymerization led to the identification and/or isolation of well-defined cyclic species. [53][54][55][56][57] In support of our assumption that 4 and subsequently cyclo[n]pyrrole might be produced electrochemically from 3,4-diethyl pyrrole 5, we note a recent contribution from Kita and co-workers, [58] wherein 4 was produced directly from 5 through the oxidative coupling of the corresponding cation radicals formed in situ by treatment with phenyliodine bis(trifluoroacetate) (PIFA) and bromotrimethylsilane.…”

Section: Resultssupporting

confidence: 51%

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Electrochemical Syntheses of Cyclo[n]pyrrole

Buda

Iordache

Bucher

et al. 2010

Chemistry A European J

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Cyclo[8]pyrrole was obtained efficiently when 3,3',4,4'-tetraethylbipyrrole was subjected to bulk electrolysis, with yields spanning a range from close to 0 % with tetra-n-butylammonium fluoride as the electrolyte, to almost 70 % when tetra-n-butylammonium hydrogensulfate was used for this purpose. These observations are consistent with the conclusion that the reaction is controlled by anion-related factors such as a specific templating effect. Note that cyclo[8]pyrrole was the only detectable macrocyclic product obtained from 3,3',4,4'-tetraethylbipyrrole under the conditions of the electrochemical oxidation. When similar electrolyses were performed by using 3,4-diethylpyrrole as the starting material, two products could be isolated, which were identified as being the cyclo[7]pyrrole and cyclo[8]pyrrole, respectively. Detailed analyses of the oxidized forms of cyclo[7]pyrrole and cyclo[8]pyrrole revealed that under the conditions of the electrolysis these latter species are not stable.

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Section: Resultssupporting

confidence: 91%

Section: Resultssupporting

confidence: 51%

Electrochemical Syntheses of Cyclo[n]pyrrole

Buda

Iordache

Bucher

et al. 2010

Chemistry A European J

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“…In a preliminary stage the deposition of PPy-3-carbox was performed by cyclic voltammetry between -0.5 and 1.5 V; the corresponding first and last (5 th ) cycles are shown in Figure 1. The first anodic scan shows a wide peak, pertaining to the oxidation of pyrrole-3-carboxylic acid, whose potential (+ 1.37 V) is higher than the one observed for pyrrole monomer, as expected, due to the presence of an electron-attractive substituent on the pyrrole ring [31][32] . Moreover, monomer oxidation seems to be totally irreversible, since no peak related to the reduction of the oxidized monomer can be recorded after reversing the potential scan.…”

Section: Electrochemical Characterization Of Ppy-3-carboxmentioning

confidence: 93%

“…This phenomenon has been observed also for polypyrrole and is known as "overoxidation". Some authors 32 have already reported the formation of an insulating film, using pyrrole-3-carboxylic acid as monomer, when the anodic potentials involved in the monomer oxidation were applied during electrosynthesis. A different behaviour was observed when an anodic limit of 0.9 V was adopted for polymerization, as shown in Figure 2.…”

Section: Electrochemical Characterization Of Ppy-3-carboxmentioning

confidence: 99%

Analytical Characterization of Poly(Pyrrole‐3‐Carboxylic Acid) Films Electrosynthesised on Pt, Ti and Ti/Al/V Substrates

et al. 2004

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With the aim of developing a polymeric multilayer film for application in advanced biomaterials, as a first step poly(pyrrole-3-carboxylic acid) films (abbreviated as PPy-3-carbox) were electropolymerised from pyrrole-3-carboxylic acid solutions by cyclic voltammetry and chronoamperometry on platinum, titanium and Ti90Al6V4 substrates and characterised both electrochemically (cyclic voltammetry) and spectroscopically (X-Ray Photoelectron Spectroscopy, XPS). Electrochemical experiments showed that the potential range adopted for electropolymerization affects the polymer electroactivity, by analogy with unsubstituted polypyrrole. The combination of conventional and chemical derivation-XPS provided information on PPy-3-carbox surface structure, showing no significant difference between films grown on different substrates and an increase of the COOH groups amount (one group over three pyrrole rings, as an average) with respect to unsubstituted polypyrrole (PPy), as expected. Finally, a preliminary Time-of-Flight Secondary Ion Mass Spectrometry (ToF-SIMS) investigation was performed in order to get further information on the polymer structure and electroactivity.

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“…The polymers can be prepared by chemical or electrochemical oxidative polymerisation of the monomers. Polymers with a great variety of properties can be prepared by resorting to synthesis conditions including the choice of solvents and monomers, additive added, supporting electrolytes, the nature of the dopants, the electrodes used, as well as the final preparation technique [2,3,4,5,6,7].…”

Section: Introductionmentioning

confidence: 99%

Effect of Mobile Phase Composition on the Selectivity of Chromatography Columns Which Use Polypyrrole as the Stationary Phase

Chriswanto

2022

SCOG

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Chromatography columns packed with polymeric stationary phase have been prepared. The packing materials were prepared by depositing polypyrrole chloride or polypyrrole dodecylsulfate onto silica particles. The deposition was accomplished by chemical oxidative polymerisation. Chromatographic selectivity of the columns was examined under reversed-phase condition using pairs of test compounds with known functionalities as the probes. The results showed that if hydrophobic interactions were dominant, the selectivity increased with decreasing in organic fraction in the mobile phase, and vise versa.

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Polypyrrole from β-substituted pyrrole monomers

Cited by 22 publications

References 12 publications

Electrochemical Syntheses of Cyclo[n]pyrrole

Electrochemical Syntheses of Cyclo[n]pyrrole

Analytical Characterization of Poly(Pyrrole‐3‐Carboxylic Acid) Films Electrosynthesised on Pt, Ti and Ti/Al/V Substrates

Effect of Mobile Phase Composition on the Selectivity of Chromatography Columns Which Use Polypyrrole as the Stationary Phase

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