Dataset Information

Effect of Additives on the in situ Laccase-Catalyzed Polymerization of Aniline Onto Bacterial Cellulose.

ABSTRACT: Laccase-mediated systems are a green route to accelerate the oxidation of aniline and obtain polyaniline with conductive properties. The synthesis of green polyaniline (emeraldine salt) was herein improved by the inclusion of additives like sodium bis (2-ethyl hexyl) sulfosuccinate (AOT) and potassium hexacyanoferrate (II) (KHCF) in the medium. The aniline polymerization was confirmed by the detection of the absorption band typical of emeraldine salt at 420 nm, typical of the semiquinoid radical cation, and of the polaron absorption band at 700-800 nm, corresponding to the distinctive signal of doped or partial doped aniline. The oligomers and/or polymers obtained were characterized by spectrometry techniques, namely 1H NMR and MALDI-TOF, and the bacterial cellulose (BC) conductivity was assessed by means of a four-point probe electrical conductivity technique. The best polymerization results were obtained with 5 mM AOT, 10 mM KHCF, and 25 U/mL of laccase. The synergistic effect between both additives in the presence of a catalyst leads to obtaining BC samples coated with green polyaniline with promising electric conductive properties.

SUBMITTER: Shim E

PROVIDER: S-EPMC6812606 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Effect of Additives on the <i>in situ</i> Laccase-Catalyzed Polymerization of Aniline Onto Bacterial Cellulose.

Shim Euijin E Noro Jennifer J Cavaco-Paulo Artur A Silva Carla C Kim Hye Rim HR

Frontiers in bioengineering and biotechnology 20191017

Laccase-mediated systems are a green route to accelerate the oxidation of aniline and obtain polyaniline with conductive properties. The synthesis of green polyaniline (emeraldine salt) was herein improved by the inclusion of additives like sodium bis (2-ethyl hexyl) sulfosuccinate (AOT) and potassium hexacyanoferrate (II) (KHCF) in the medium. The aniline polymerization was confirmed by the detection of the absorption band typical of emeraldine salt at 420 nm, typical of the semiquinoid radical ...[more]

PMID: 31681744

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Project description:Many previous studies have shown that (i) the oxidation of aniline or the aniline dimer p-aminodiphenylamine (PADPA) in a slightly acidic aqueous solution can be catalyzed with heme peroxidases or multicopper laccases and that (ii) subsequent reactions lead to oligomeric or polymeric products, which resemble chemically synthesized polyaniline in its conductive emeraldine salt form (PANI-ES), provided that (iii) an anionic "template" is present in the reaction medium. Good templates are anionic polyelectrolytes, micelles, or vesicles. Under optimal conditions, their presence directs the reactions in a positive way toward the desired formation of PANI-ES-type products. The effect of four different types of anionic templates on the formation of PANI-ES-like products from PADPA was investigated and compared by using Trametes versicolor laccase (TvL) as a catalyst in an aqueous pH 3.5 solution at room temperature. All four templates contain sulfonate groups: the sodium salt of the polyelectrolyte sulfonated polystyrene (SPS), micelles from sodium dodecylbenzenesulfonate (SDBS), vesicles from a 1:1 molar mixture of SDBS and decanoic acid, and vesicles from sodium bis(2-ethylhexyl)sulfosuccinate (AOT). Although with all four templates, stable, inkjet-printable solutions or suspensions consisting of PANI-ES-type products were obtained under optimized conditions, considerably higher amounts of TvL were required with SDBS micelles to achieve comparable monomer conversion to PANI-ES-like products during the same time period when compared to those with SPS or the two types of vesicles. This makes SDBS micelles less attractive as templates for the investigated reaction. In situ UV/vis/near-infrared, electron paramagnetic resonance (EPR), and Raman spectroscopy measurements in combination with an high-performance liquid chromatography analysis of extracted reaction products, which were deprotonated and chemically reduced, showed seemingly small but significant differences in the composition of the mixtures obtained when reaching reaction equilibrium after 24 h. With the two vesicle systems, the content of unwanted substituted phenazine units was lower than in the case of SPS polyelectrolyte and SDBS micelles. The EPR spectra indicate a more localized, narrower distribution of electronic states of the paramagnetic centers of the PANI-ES-type products synthesized in the presence of the two vesicle systems when compared to that of the similar products obtained with the SPS polyelectrolyte and SDBS micelles as templates. Overall, the data obtained from the different complementary methods indicate that with the two vesicle systems structurally more uniform (regular) PANI-ES-type products formed. Among the two investigated vesicle systems, for the investigated reaction (oxidation of PADPA with TvL and O2), AOT appears a somewhat better choice as it leads to a higher content of the PANI-ES polaron form.

Dataset Information

Effect of Additives on the in situ Laccase-Catalyzed Polymerization of Aniline Onto Bacterial Cellulose.

Publications

Effect of Additives on the <i>in situ</i> Laccase-Catalyzed Polymerization of Aniline Onto Bacterial Cellulose.

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