A multifrequency EPR study of poly(PADPA) synthesized with Trametes versicolor laccase from the aniline dimer p-aminodiphenylamine (PADPA) in the presence of anionic vesicles

Carić, Dejana; Rakvin, Boris; Kveder, Marina; Junker, Katja; Walde, Peter; Reijerse, Edward J.

doi:10.1016/j.cap.2015.08.023

Cited by 7 publications

(10 citation statements)

References 24 publications

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“…Recently, the same was also found for the aniline dimer N ‐phenyl‐1,4‐phenylenediamine (= p ‐aminodiphenylamine, PADPA ( 2 ), Fig. ) . In all mentioned cases of 1 or 2 , conditions were found under which the main products obtained in the presence of the templates are oligomers or polymers which have characteristic properties that are typical for the conductive emeraldine salt form of polyaniline (PANI‐ES; 3 ), see Fig.…”

Section: Introductionsupporting

confidence: 54%

“…shows the kinetics of the reaction with AOT vesicles monitored with UV/VIS‐NIR spectroscopy after reaction times of 30 min, 1, 2, 4, 24 and 48 h. After 48 h, the band at 1000 nm reached an absorbance of about 0.75 ( l = 0.1 cm). Compared to the PADPA/AOT vesicle systems studied previously with the oxidative enzymes TvL or HRPC, the reaction with cyt c was very slow, as in those previous cases the same absorbance at 1000 nm was reached already after 1 – 2 h . In addition to the band in the NIR (at ca .…”

Section: Resultsmentioning

confidence: 59%

“…In at least two examples, the template‐assisted enzymatic formation of a PANI‐ES type product from 2 was proven undoubtedly . This product was obtained in suspensions of 80 – 100 nm‐sized AOT vesicles with either Trametes versicolor laccase (TvL) and dissolved dioxygen (O 2 ) from air at pH = 3.5, or with horseradish peroxidase isoenzyme C (HRPC) and added hydrogen peroxide (H 2 O 2 ) at pH = 4.3 . In the case of the laccase system, the PANI‐ES type product was found to be the linear N‐C‐ para coupled PADPA dimer as emeraldine salt (in about 50% yield), i.e., the protonated half‐oxidized and half‐reduced linear tetraaniline, which is the shortest possible PANI‐ES type molecule.…”

Section: Introductionmentioning

confidence: 99%

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A Novel Role of Vesicles as Templates for the Oxidation and Oligomerization ofp‐Aminodiphenylamine by Cytochromec

Luginbühl

Iwasaki

Varkey

et al. 2017

Helvetica Chimica Acta

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The oxidation and subsequent oligo‐ or polymerization of aniline or the N‐C‐para coupled aniline dimer p‐aminodiphenylamine (N‐phenyl‐1,4‐phenylenediamine) with H2O2‐dependent heme peroxidases in aqueous medium at pH = 4.3 is strongly influenced in a positive way by the presence of anionic polymers, micelles or vesicles as soft ‘templates’ (macromolecular or polymolecular additives), to yield products which resemble the emeraldine salt form of polyaniline (PANI‐ES). The positive effect the templates exert on the reaction mainly originates from interactions between the templates and the monomers, reaction intermediates and products, whereby the reaction occurs localized in the vicinity of the templates, suppressing undesired side reactions. As shown in the present work, the templates may even play an additional role, depending on the type of catalyst. Through interactions between the heme protein cytochrome c and anionic vesicles, cytochrome c gains increased peroxidase activity. In this way, the templates not only serve for hosting the oxidation and oligo‐ or polymerization reactions for obtaining PANI‐ES type products, but also simultaneously activate the catalyst in order to trigger the reaction.

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Section: Introductionsupporting

confidence: 54%

Section: Resultsmentioning

confidence: 59%

Section: Introductionmentioning

confidence: 99%

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A Novel Role of Vesicles as Templates for the Oxidation and Oligomerization ofp‐Aminodiphenylamine by Cytochromec

Luginbühl

Iwasaki

Varkey

et al. 2017

Helvetica Chimica Acta

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“…This is important to keep in mind if the physical properties of solid, isolated poly(PADPA)-AOT products5253 are compared with the physical properties of “as-obtained” products.…”

Section: Discussionmentioning

confidence: 99%

Insight into the template effect of vesicles on the laccase-catalyzed oligomerization of N-phenyl-1,4-phenylenediamine from Raman spectroscopy and cyclic voltammetry measurements

Ležaić

Luginbühl

Bajuk–Bogdanović

et al. 2016

Sci Rep

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We report about the first Raman spectroscopy study of a vesicle-assisted enzyme-catalyzed oligomerization reaction. The aniline dimer N-phenyl-1,4-phenylenediamine (= p-aminodiphenylamine, PADPA) was oxidized and oligomerized with Trametes versicolor laccase and dissolved O2 in the presence of sodium bis(2-ethylhexyl)sulfosuccinate (AOT) vesicles (80–100 nm diameter) as templates. The conversion of PADPA into oligomeric products, poly(PADPA), was monitored during the reaction by in situ Raman spectroscopy. The results obtained are compared with UV/vis/NIR and EPR measurements. All three complementary methods indicate that at least some of the poly(PADPA) products, formed in the presence of AOT vesicles, resemble the conductive emeraldine salt form of polyaniline (PANI-ES). The Raman measurements also show that structural units different from those of “ordinary” PANI-ES are present too. Without vesicles PANI-ES-like products are not obtained. For the first time, the as-prepared stable poly(PADPA)-AOT vesicle suspension was used directly to coat electrodes (without product isolation) for investigating redox activities of poly(PADPA) by cyclic voltammetry (CV). CV showed that poly(PADPA) produced with vesicles is redox active not only at pH 1.1–as expected for PANI-ES–but also at pH 6.0, unlike PANI-ES and poly(PADPA) synthesized without vesicles. This extended pH range of the redox activity of poly(PADPA) is important for applications.

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“…The obtained PADPA oligomers prevalently have the molecular structure of emeraldine salt. Poly(PADPA) was also synthesized with TvL and O 2 at pH 3.5 in an aqueous solution in the presence of AOT vesicles as templates (Junker et al 2014b; Carić et al 2015; Janošević-Ležaić et al 2016) (Fig. 17).…”

Section: Enzymatic Polymerization Of Substituted Anilines and Other Amentioning

confidence: 99%

Enzymatic oligomerization and polymerization of arylamines: state of the art and perspectives

et al. 2016

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The literature concerning the oxidative oligomerization and polymerization of various arylamines, e.g., aniline, substituted anilines, aminonaphthalene and its derivatives, catalyzed by oxidoreductases, such as laccases and peroxidases, in aqueous, organic, and mixed aqueous organic monophasic or biphasic media, is reviewed. An overview of template-free as well as template-assisted enzymatic syntheses of oligomers and polymers of arylamines is given. Special attention is paid to mechanistic aspects of these biocatalytic processes. Because of the nontoxicity of oxidoreductases and their high catalytic efficiency, as well as high selectivity of enzymatic oligomerizations/polymerizations under mild conditions—using mainly water as a solvent and often resulting in minimal byproduct formation—enzymatic oligomerizations and polymerizations of arylamines are environmentally friendly and significantly contribute to a “green” chemistry of conducting and redox-active oligomers and polymers. Current and potential future applications of enzymatic polymerization processes and enzymatically synthesized oligo/polyarylamines are discussed.

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A multifrequency EPR study of poly(PADPA) synthesized with Trametes versicolor laccase from the aniline dimer p-aminodiphenylamine (PADPA) in the presence of anionic vesicles

Cited by 7 publications

References 24 publications

A Novel Role of Vesicles as Templates for the Oxidation and Oligomerization ofp‐Aminodiphenylamine by Cytochromec

A Novel Role of Vesicles as Templates for the Oxidation and Oligomerization ofp‐Aminodiphenylamine by Cytochromec

Insight into the template effect of vesicles on the laccase-catalyzed oligomerization of N-phenyl-1,4-phenylenediamine from Raman spectroscopy and cyclic voltammetry measurements

Enzymatic oligomerization and polymerization of arylamines: state of the art and perspectives

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