One pot biocatalytic synthesis of a biodegradable electroactive macromonomer based on 3,4-ethylenedioxytiophene and poly( l -lactic acid)

Silva, Aruã Clayton Da; Augusto, Tatiana; Andrade, Leandro H.; Torresi, Susana I. Córdoba de

doi:10.1016/j.msec.2017.09.007

Cited by 33 publications

(35 citation statements)

References 59 publications

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“…Herein, we decided to use the organometallic catalyst for the synthesis in order to obtain a higher molecular weight of the PDLLA chain, aiming better final properties in terms of processability (ease in obtaining films by spin coating and solubility in organic solvents). In our previous study, 33 it was found that EDOT-PDLLA can be electropolymerized, but only a few oligomers can be obtained, with no adhesion to the electrode surface, probably due to the increased solubility in organic solvent of the PDLLA part.…”

Section: Synthesis Of the Au/pedot-pdlla Nanocompositesmentioning

confidence: 96%

“…The first step of the one-pot synthesis of a modified electroactive macromonomer based on EDOT-PDLLA was developed by our group 33 (Figure 1a). Herein, we decided to use the organometallic catalyst for the synthesis in order to obtain a higher molecular weight of the PDLLA chain, aiming better final properties in terms of processability (ease in obtaining films by spin coating and solubility in organic solvents).…”

Section: Synthesis Of the Au/pedot-pdlla Nanocompositesmentioning

confidence: 99%

“…The multiplets at 5.15 and 1.50 ppm are attributed to the CH and CH 3 of the PDLLA chain, respectively. The singlet in 6.36 ppm corresponds to hydrogen electropolymerizable on thiophene group (vicinal to sulfur) and it is well defined for EDOT-PDLLA, 33 while for PEDOT-co-PDLLA spectrum (blue) it is weaker and there are some shift to higher chemical shifts as a multiplet due to the different PEDOT chain lengths. For the Au/o-EDOT-PDLLA spectrum the same signal is very weak and looks like a multiplet, suggesting the oligomerization of EDOT-PDLLA.…”

Section: Spectroscopic Characterization Of Au/pedot-pdlla Nanocompositesmentioning

confidence: 99%

“…For the Au/o-EDOT-PDLLA spectrum the same signal is very weak and looks like a multiplet, suggesting the oligomerization of EDOT-PDLLA. Additionally, at the region of 3.95-4.45 ppm it was possible to see a welldefined singlet at 4.20 ppm for the PEDOT-co-PDLLA spectrum, which corresponds to the hydrogens close to ethylenedioxy group on PEDOT chains which is not present on EDOT-PDLLA (black) because the modified EDOT-CH 2 -OH have substituents on ethylenedioxy group leading for three multiplet-like signals in the same region, 33 but the Au/o-EDOT-PDLLA nanocomposite (pink) presents a multiplet stronger and shifted to a lower chemical shift values, reinforcing the idea of oligomerization of EDOT-PDLLA. Figure 4b presents Raman spectra of Au/PEDOT-PDLLA nanocomposite film covering GCE (top), pure Au/PEDOT-PDLLA nanocomposite (middle) and PEDOT-PSS (bottom).…”

Section: Spectroscopic Characterization Of Au/pedot-pdlla Nanocompositesmentioning

confidence: 99%

“…For biomedical applications, conducting polymers usually present some advantages towards metals and semiconductors in terms of biocompatibility, but modification strategies are usually required to improve them when thinking in a device. 32 Recently, it was reported by our group the synthesis of a new electroactive macromonomer of 3,4-ethylenedioxythiophene (EDOT)-PDLLA, 33 which can play an important role in the synthesis of different conducting and biodegradable materials based on PEDOT and PDLLA chemistry. The polymerization of this electroactive macromonomer was tried by electrochemical methods, but (i) only oligomers were formed due to the high solubility in organic solvents, and (ii) no electroactive properties were found.…”

Section: Introductionmentioning

confidence: 99%

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Gold Nanoparticles and [PEDOT-Poly(D,L-Lactic Acid)] Composite: Synthesis, Characterization and Application to H2O2 Sensing

Silva¹,

Minadeo²,

Torresi³

2019

J. Braz. Chem. Soc.

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Biocompatible electrochemical devices are challenging to develop due to the toxicity of many advanced electrode materials and the difficulty to degrade the discarded material. Few recent advances were made in the synthesis of conducting biodegradable composites of polymers for electrode materials. In this article we describe the synthesis of two new inorganic/organic nanocomposites of Au nanoparticles and conducting polymers based on the biodegradable polymer poly(D,L-lactic acid) (PDLLA): Au nanoparticles/oligomers of 3,4-ethylenedioxythiophene (EDOT)-PDLLA and Au nanoparticles with poly(3,4-ethylenedioxythiophene) (PEDOT)-PDLLA. The nanocomposites were carefully analyzed; the gold nanoparticles mean sizes were 8 ± 3 and 7 ± 2 nm, respectively. 1 H and 13 C nuclear magnetic resonance (NMR) demonstrated the polymerization of EDOT-PDLLA made through one-pot reaction with Au III precursor. Raman spectra show that PEDOT-PDLLA is formed in the synthesis of Au/PEDOT-PDLLA. The immobilization of Au/PEDOT-PDLLA on glassy carbon electrodes is easy and more stable than the immobilization of simple PEDOT. Au/PEDOT-PDLLA catalyzes the reduction of H 2 O 2(aq) , which was detected by chronoamperometry. The sensor is stable and presents sensitivity of 8.36 × 10 −3 A mol −1 L cm −2 , linear range of 1-45 mmol L −1 and limit of detection of 0.17 mmol L −1 .

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Section: Synthesis Of the Au/pedot-pdlla Nanocompositesmentioning

confidence: 96%

Section: Synthesis Of the Au/pedot-pdlla Nanocompositesmentioning

confidence: 99%

Section: Spectroscopic Characterization Of Au/pedot-pdlla Nanocompositesmentioning

confidence: 99%

Section: Spectroscopic Characterization Of Au/pedot-pdlla Nanocompositesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Gold Nanoparticles and [PEDOT-Poly(D,L-Lactic Acid)] Composite: Synthesis, Characterization and Application to H2O2 Sensing

Silva¹,

Minadeo²,

Torresi³

2019

J. Braz. Chem. Soc.

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Electrical/Spectroscopic Stability of Conducting and Biodegradable Graft‐Copolymer

Silva

Paschoal

Ribeiro

et al. 2022

Macro Chemistry & Physics

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3D Printable Conducting and Biocompatible PEDOT‐graft‐PLA Copolymers by Direct Ink Writing

Dominguez‐Alfaro

Gabirondo

Alegret

et al. 2021

Macromol. Rapid Commun.

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Tailor‐made polymers are needed to fully exploit the possibilities of additive manufacturing, constructing complex, and functional devices in areas such as bioelectronics. In this paper, the synthesis of a conducting and biocompatible graft copolymer which can be 3D printed using direct melting extrusion methods is shown. For this purpose, graft copolymers composed by conducting polymer poly(3,4‐ethylenedioxythiophene) (PEDOT) and a biocompatible polymer polylactide (PLA) are designed. The PEDOT‐g‐PLA copolymers are synthesized by chemical oxidative polymerization between 3,4‐ethylenedioxythiophene and PLA macromonomers. PEDOT‐g‐PLA copolymers with different compositions are obtained and fully characterized. The rheological characterization indicates that copolymers containing below 20 wt% of PEDOT show the right complex viscosity values suitable for direct ink writing (DIW). The 3D printing tests using the DIW methodology allows printing different parts with different shapes with high resolution (200 µm). The conductive and biocompatible printed patterns of PEDOT‐g‐PLA show excellent cell growth and maturation of neonatal cardiac myocytes cocultured with fibroblasts.

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One pot biocatalytic synthesis of a biodegradable electroactive macromonomer based on 3,4-ethylenedioxytiophene and poly( l -lactic acid)

Cited by 33 publications

References 59 publications

Gold Nanoparticles and [PEDOT-Poly(D,L-Lactic Acid)] Composite: Synthesis, Characterization and Application to H2O2 Sensing

Gold Nanoparticles and [PEDOT-Poly(D,L-Lactic Acid)] Composite: Synthesis, Characterization and Application to H2O2 Sensing

Electrical/Spectroscopic Stability of Conducting and Biodegradable Graft‐Copolymer

3D Printable Conducting and Biocompatible PEDOT‐graft‐PLA Copolymers by Direct Ink Writing

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