Electrochemical synthesis and spectroelectrochemical behavior of poly(diphenylamine-co-4,4′-diaminodiphenyl sulfone)

Manisankar, P.; Ilangeswaran, D.

doi:10.1016/j.electacta.2010.06.023

Cited by 18 publications

(12 citation statements)

References 32 publications

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“…It was observed that the film exhibits electroactivity only up to pH 7.0. Figure 3b shows As previously stated, Manisankar and co-workers [5][6][7][8] prepared dapsone films in a wide potential window (0.0 to ≥ 1.3 V) which blocked the electrode surface. We carried out an experiment similar to theirs, using a wider potential window (0.00 to 1.50 V), while keeping the other parameters the same (scan rate of 1.00 V s  and pH 1.0).…”

Section: Accepted Manuscriptmentioning

confidence: 60%

“…In such conditions, they showed that dapsone undergoes an irreversible oxidation process in the potential range of 1.1 to 1.9 V using Ag/AgCl reference electrode, and they attributed the current signal loss after the first anodic scan to the homopolymerization of dapsone [5,6,8], with the resulting formation of a low conductive film.…”

Section: Introductionmentioning

confidence: 97%

“…Polydapsone belongs to this family, and the first report found on its synthesis is attributed to Dan and Sengupta [2], who prepared the polymer through a chemical oxidative method. Thereafter, conductive copolymers of dapsone with aniline [3], pyrrole [4], diphenylamine [5], and 4-aminodiphenylamine [6] have been prepared through chemical and electrochemical methods, showing electroactivity.…”

Section: Introductionmentioning

confidence: 99%

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Conductive organic polymers: An electrochemical route for the polymerization of dapsone

Moura

Júnior

Machado

et al. 2015

Journal of Electroanalytical Chemistry

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The electropolymerization of dapsone by anodic oxidation is reported for the first time. The conditions in which a non-conducting oligomeric film or a conductive polymeric film of dapsone is formed are also discussed, based on the scan rate and potential window applied. The cyclic voltammetry of dapsone-polymer presented redox activities that have not been shown before, to the authors' knowledge, demonstrating its high electronic conductivity. The electrochemical impedance response of the dapsone-polymer indicates that their admittance is similar to pure and sulfonated polyanilines, while for the dapsone-oligomers is characteristic of insulating materials. Infrared spectroscopy of both oligomers and polymer supports that the polymerization occurs via amino-amino coupling, since no modifications in the aromatic ring is observed.KEYWORDS. polydapsone, electropolymerization, conductive polymer, Fe +3 /Fe +2 redox couple, polyaniline. Graphical abstract -0.2 0.0 0.2 0.4 0.6 0.8 -50 -40 -30 -20 -10 0 10 20 30 40 GCE GCE/Dapsone-Polymer GCE/Dapsone-Oligomers E / V (vs. Ag/AgCl) Fe +3 /Fe +2 redox couple

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Section: Accepted Manuscriptmentioning

confidence: 60%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

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Conductive organic polymers: An electrochemical route for the polymerization of dapsone

Moura

Júnior

Machado

et al. 2015

Journal of Electroanalytical Chemistry

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“…Perhaps the most compelling evidence for a mechanism involving proton transfer and CTC formation between the MA and PADPA are the new peaks at 3089 and 1698 cm −1 assigned to OH stretching in hydrogen‐bonded COOH and carbonyl C=O stretching of the COOH group of MA–PADPA adduct, respectively. The bands observed at 1496 and 1241 cm −1 correspond to benzenoid ring C=C stretching vibrations and the C−N stretching of the secondary aromatic amine, respectively . Evidence for a MA–PADPA complex is the NH stretching band of the amide at 3268 cm −1 (Figure c).…”

Section: Resultsmentioning

confidence: 96%

“…Peaks corresponding to the benzenoid ring protons at 6.82 (doublet) and 6.76 ppm (doublet) can be observed as overlapped peaks at 7.03 ppm (4 H) in the spectrum of the mixture. Also, the proton of the secondary NH group at 7.45 ppm (f) shifts to 8.15 ppm (1 H; f) …”

Section: Resultsmentioning

confidence: 99%

Charge‐Transfer Complex of p‐Aminodiphenylamine with Maleic Anhydride: Spectroscopic, Electrochemical, and Physical Properties

et al. 2016

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A new charge-transfer complex and the amide formed by the interaction between the electron donor of the p-aminodiphenylamine and the electron acceptor of maleic anhydride are investigated by spectroscopic methods. The amidation reaction is caused by proton and charge transfer between the maleic anhydride and p-aminodiphenylamine molecules. The Benesi-Hildebrand equation is used to determine the formation constant, the molar extinction coefficient and the standard Gibbs free energy of the complex by using UV/Vis spectroscopy. To reveal the electronic and spectroscopic properties of these molecules, theoretical computations are performed on the structures of maleic anhydride, p-aminodiphenylamine and the conformers of their charge-transfer complex. The charge-transfer complex and amidation reaction mechanism are also confirmed by IR and NMR spectroscopy and HRMS. The nature of the maleic anhydride-p-aminodiphenylamine complex is characterized by cyclic voltammetry, thermogravimetric analysis, XRD and SEM. Solid microribbons of this complex show higher thermal stability than p-aminodiphenylamine.

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High glass transition and thermally stable polynorbornenes containing fluorescent dipyrene moieties via ring‐opening metathesis polymerization

Lian

Wang

et al. 2011

J. Polym. Sci. A Polym. Chem.

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A high‐glass‐transition‐temperature polynorbornene, poly(NBEDPY), containing chromophore groups was synthesized by ring‐opening metathesis polymerization (ROMP) using Grubbs' catalysts; poly(HNBEDPY) was obtained by the reduction of poly(NBEDPY). The glass transition temperatures (Tg) of poly(NBEDPY) and hydrogenated poly(HNBEDPY) were as high as 250 °C and 220 °C, respectively, because of the rigid dipyrene groups, which are higher than those of commercially available ring‐opened hydrogenated polynorbornenes (JSR ARTON®; 120–165 °C). The 10% weight‐loss temperatures of hydrogenated poly(HNBEDPY) and poly(NBEDPY) were up to 450 °C and 400 °C, respectively. A hydrogenated poly (HNBEDPY) film showed excellent transparency (over 91%). The photoluminescence emission spectra of poly(HNBEDPY) showed strong solvent‐polarity dependence, revealing that poly (HNBEDPY) underwent remarkable bathochromic shifts with an increase in solvent polarity. Poly(HNBEDPY) also showed remarkable fluorescent solvatochromism (blue in toluene, greenish yellow in dimethyl sulfoxide). The cyclic voltammogram of poly(HNBEDPY) film cast onto an indium tin oxide (ITO)‐coated glass substrate exhibited one reversible oxidation redox couple at 0.55 V versus Ag/Ag+ in acetonitrile solution. The electrochromic characteristics of poly(HNBEDPY) showed reversibility, with a color change from its green neutral form to dark red upon the application of potentials from 0 to 1.0 V. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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Electrochemical synthesis and spectroelectrochemical behavior of poly(diphenylamine-co-4,4′-diaminodiphenyl sulfone)

Cited by 18 publications

References 32 publications

Conductive organic polymers: An electrochemical route for the polymerization of dapsone

Conductive organic polymers: An electrochemical route for the polymerization of dapsone

Charge‐Transfer Complex of p‐Aminodiphenylamine with Maleic Anhydride: Spectroscopic, Electrochemical, and Physical Properties

High glass transition and thermally stable polynorbornenes containing fluorescent dipyrene moieties via ring‐opening metathesis polymerization

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