Anodic oxidation of dipyrrolyls linked with conjugated spacers: study of electronic interactions between the polypyrrole chain and the spacers

Just, P.-E.; Chane-Ching, Kathleen I.; Lacroix, Jean-Claude; Lacaze, P.C.

doi:10.1016/s0022-0728(99)00420-9

Cited by 22 publications

(12 citation statements)

References 25 publications

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“…Therefore, our results can be interpreted in terms of an increase of conjugative effects of the para substituents on the phenyl ring, also producing an electronic interaction with the pyrrole ring. Indeed, as previously pointed out by Just et al, 16 the conjugation interaction occurring between the p-substituted phenyl and the pyrrole groups might influence the electron density distribution on the pyrrole ring, modifying the oxidation potential. In the case of 6, the Fig 3 insert shows a linear variation of the intensity of the three anodic peaks located at 1.3, 1.1, and 0.8 V/SCE, (corresponding respectively to the thiophene, benzene and pyrrole ring oxidation) with the scan rate square root (v 1/2 ), which indicates that the redox process on all three oxidation sites of 6 is controlled by the electroactive monomer diffusion in solution.…”

Section: Electrochemical Propertiesmentioning

confidence: 76%

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New synthesis routes, characterization, electrochemical and spectral properties of p-substituted N-phenylpyrroles. Substituent effects

Diaw¹,

Yassar²,

Gningue-Sall³

et al. 2009

Arkivoc

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A series of p-substituted N-phenylpyrroles, including 4-(1H-pyrrol-1-yl)phenol (1), 1-(4-methoxyphenyl)-1H-pyrrole (2), 1,1'-benzene-1,4-diylbis(1H-pyrrole) (4), 1,1'-biphenyl-4,4'-diylbis(1H-pyrrole) (5) and 1-(4-bromophenyl)-1H-pyrrole (3), was prepared by means of a modified Clauson-Kaas method. Two new symmetrically and asymmetrically end-capped pyrrole thiophenes, namely 1-[4-(thiophen-2-yl)phenyl]-1H-pyrrole (6) and 1,1'-(bithiophen-5,5''-diyldibenzene-4,1-diyl)bis(1H-pyrrole) (7) were synthesized by using 3 as a building block and the Stille method as cross-coupling reaction. For both methods, the chemical yields ranged from 36 to 81% and the desired products were characterized by 1 H and 13 C NMR, IR, and mass spectrometry. Electrochemical properties and UV-visible absorption spectra were also investigated in order to evaluate the substituent electron-donor effects on the physicochemical parameters.

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Section: Electrochemical Propertiesmentioning

confidence: 76%

“…The light brown crystals were filtered off, washed with acetic acid and ether and dried. Crystallization from acetic acid afforded 1.87 g (36 %) of 4, mp 229 °C (literature: 228 °C 16 ). …”

Section: Methodsmentioning

confidence: 99%

New synthesis routes, characterization, electrochemical and spectral properties of p-substituted N-phenylpyrroles. Substituent effects

Diaw¹,

Yassar²,

Gningue-Sall³

et al. 2009

Arkivoc

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“…This product is then filtered and washed with acetic acid and ether. The condensation reaction of 2,5-dimethoxytetrahydrofuran and p-phenylenediamine in the ratio 1:2 (mol:mol) has led after 20-25 min to the formation of 1.87 g (36 %) of 1,1'-phenylenedipyrridyl (Scheme-I), with T f = 229 °C (literature: 228 °C 32 ). Mechanism of the synthesis reaction: The synthesis of PhDPy and DPhDPy was realized according to the method proposed by Clauson-Kaas 31 and as described in our previous paper 28 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Electropolymerization of New Phenylene-Substituted Dipyrridyls: Electrochemical and Spectroscopic Characterization

Diaw¹,

Fall²,

Gningue-Sall³

et al. 2014

Asian J. Chem.

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Pyrrole is one of the most used heterocyclic compounds because of the increasing interest which it arouses regarding medicnal chemistry, organic synthesis and chemistry of materials 1-7. Consequently, various synthesis procedures were developed for pyrrole and its derivatives. Among these procedures, we can quote the following classic methods: (i) Hantzsch reaction 8,9 , which allows one to obtain pyrrole from the reaction between α-chloromethyl ketone, β-ketoester and ammonia water. (ii) Knorr reaction 10-14 , leading to pyrrole by reaction between α-aminoketone and β-ketoester. (iii) Paal Knorr reaction 15 which allows to obtain pyrrole by condensation of 2,5-dimethoxytetrahydrofuran and one primary amine. The interest of monomers stemming from these diverse modes of synthesis made of the chemistry of materials a much widened domain where organic chemists, electrochemists and

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“…These materials may be described, in general, as polymers that can be converted into materials having many or all of the properties of a metal (even when they are insulators or semiconductors as synthesized). This conversion can be brought about through appropriate chemical or electrochemical oxidation or reduction [1][2][3][4][5][6][7][8][9][10][11][12], a process called doping (p-doping for oxidation and n-doping for reduction). The conductivity of the polymer depends on the nature and amount of the doping.…”

Section: Introductionmentioning

confidence: 99%

In situ generation of polyaniline in poly(dimethylsiloxane) networks

et al. 2005

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Polyaniline (PANI) is one of the most studied and most stable electrically conductive polymers, with the conductive form being the navy blue emeraldine salt. However, PANI is very difficult to process and displays poor mechanical performance, which suggests improving its properties by developing composite systems. In the present approach, PANI was generated in situ in poly(dimethylsiloxane) (PDMS) networks. The color of the composites varied from brown, to blue, to greenish blue, with the blue samples being the most conductive. The chemical structures of the samples were studied using FT-IR/ATR spectroscopy, which confirmed that there was more conjugation in the more conductive samples.

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Anodic oxidation of dipyrrolyls linked with conjugated spacers: study of electronic interactions between the polypyrrole chain and the spacers

Cited by 22 publications

References 25 publications

New synthesis routes, characterization, electrochemical and spectral properties of p-substituted N-phenylpyrroles. Substituent effects

New synthesis routes, characterization, electrochemical and spectral properties of p-substituted N-phenylpyrroles. Substituent effects

Synthesis and Electropolymerization of New Phenylene-Substituted Dipyrridyls: Electrochemical and Spectroscopic Characterization

In situ generation of polyaniline in poly(dimethylsiloxane) networks

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