Oligo-3-hydroxybutyrate functionalised pyrroles for preparation of biodegradable conductive polymers

Domagala, Anna; Maksymiak, Magdalena; Janeczek, Henryk; Musioł, Marta; Turczyn, Roman; Ledwon, Przemyslaw; Kaczmarczyk, Bożena; Kurcok, Piotr; Adamus, Grażyna; Kowalczuk, Marek; Łapkowski, Mieczysław

doi:10.1007/s10853-014-8241-0

Cited by 13 publications

(10 citation statements)

References 43 publications

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“…Drawing on our previous experiences with preparation of pyrrole functionalized with OHB, the reactions were targeted to obtain 3 (HB 3 ), 6 (HB 6 ) or 12 (HB 12 ) HB units in the side chain.…”

Section: Resultsmentioning

confidence: 99%

“…Functionalized PPy were prepared in two steps. First, 1‐(2‐cyanoethyl)pyrrole was hydrolysed to 1‐(2‐carboxyethyl)pyrrole according to the literature by the addition of 5 mL of 1‐(2‐cyanoethyl)pyrrole to 40 mL of KOH (6.7 mol L −1 ) under argon . This mixture was heated to reflux under an inert atmosphere until a red solution was obtained and no more NH 3 (g) evolved.…”

Section: Methodsmentioning

confidence: 99%

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N‐Oligo(3‐hydroxybutyrate)‐functionalized polypyrroles: towards bio‐erodible conducting copolymers

Domagala

Domagała

Ledwon

et al. 2016

Polymer International

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New copolymer materials have been prepared by chemical grafting of 3-hydroxybutyric acid oligomers (OHB) onto polypyrrole (PPy) derivatives. The influence of different grafting density and molecular weight of OHB brushes on physicochemical properties of prepared copolymers was investigated. Polypyrrole substrates were prepared by FeCl 3 driven oxidative homopolymerization of N-(2-carboxyethyl)pyrrole or its copolymerization with pyrrole. The grafting method employed involved controlled anionic polymerization of β-butyrolactone on pyrrole tethered potassium carboxylate active sites.Obtained polypyrrole-g-OHB copolymers of varying grafting density and pendant polyester chain length were characterized and the observed structure -property relationships discussed.The impact of real time exposure in phosphate buffered saline environment was investigated and the residue products were characterized. Cross-correlation of spectroscopic, thermal, electrical and elemental analysis data afforded comprehensive evaluation of the structure of the prepared materials and their behavior in hydrolytic medium. Erosion and degradation pathways have been identified indicating ways to consciously tailor the physicochemical properties of these new biomimetic materials.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

N‐Oligo(3‐hydroxybutyrate)‐functionalized polypyrroles: towards bio‐erodible conducting copolymers

Domagala

Domagała

Ledwon

et al. 2016

Polymer International

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“…The crude pyrrole grafted PCL (Py‐g‐PCL) were obtained and dissolved with a small amount of CH 2 Cl 2 and precipitated in an excessive amount of diethyl ether. This procedure was repeated for three times and the polymers were dried in a vacuum oven at 30°C for 48 h. …”

Section: Methodsmentioning

confidence: 99%

“…The crude pyrrole grafted PCL (Py-g-PCL) were obtained and dissolved with a small amount of CH 2 Cl 2 and precipitated in an excessive amount of diethyl ether. This procedure was repeated for three times and the polymers were dried in a vacuum oven at 30°C for 48 h. [16] Poly (ɛ-caprolactone) grafted polypyrrole was prepared via radical polymerization of Py-g-PCL using FeCl 3 , SDS and acetonitrile as initiator, dopant, and solvent, respectively. In a typical experiment, Py-g-PCL and Py (molar ratio, 2:1) were dissolved in 50 ml acetonitrile, and then FeCl 3 (6.75 g) and SDS (0.02 g) were added at À17°C.…”

Section: Synthesis Of Poly (ɛ-Caprolactone) Grafted Polypyrrolementioning

confidence: 99%

Aligned poly (glycolide‐lactide) fiber membranes with conducting polypyrrole

Guo

Qiao

Jiang

et al. 2016

Polymers for Advanced Techs

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Electroactive polypyrrole (PPy) are highly attractive for a number of biomedical applications such as tissue engineering. To improve interfacial compatibility of PPy with biopolyesters, poly (ɛ‐caprolactone) grafted PPy (PPy‐g‐PCL) are synthesized in this work and characterized with Fourier transform infrared and nuclear magnetic resonance. PPy‐g‐PCL exhibits good conductivity and electrochemical activity. It is also blended with poly (glycolide‐lactide) to make aligned fiber membranes via drum at the speed of 1500 r/min. The relationships of blending ratio with the fibrous structure, thermal stability, wettability, and mechanical properties are clarified. The results show that blending PPy‐g‐PCL has no significant effect on the fibrous morphology, but fibers trends aligned architecture as the blend ratio of poly (glycolide‐lactide)/PPy‐g‐PCL exceeds 70/30. The membranous thermal and mechanical stability are modified. The membranous hydrophilicity significantly enhances with PPy‐g‐PCL amount increasing. Then the fiber membrane with topographical and electrical cues is qualified as the application of tissue engineering. Copyright © 2016 John Wiley & Sons, Ltd.

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“…The same strategy has also been applied for the synthesis and characterization of a novel polypyrrole material grafted with biodegradable OHB pendants. The obtained OHB functionalized pyrroles were found to be promising candidates for the preparation of biodegradable conductive polymers [39,40].…”

Section: Bioactive Oligomers Of Phb Analoguementioning

confidence: 99%

Bioactive oligomers from natural polyhydroxyalkanoates and their synthetic analogues

2017

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Contemporary reports on the bioactive oligomers derived from natural aliphatic co-polyesters (PHA) and their synthetic analogues, formed through anionic ring-opening polymerization (ROP) of β-substituted β-lactones are presented. Synthetic routes for such oligomers, developed mostly by Polish authors, are discussed. The described approaches enable design of novel biodegradable and bioactive oligomers for diverse applications in medicine, cosmetic industry and agrochemistry. Otrzymywanie bioaktywnych oligomerów z naturalnych biopoliestrów i ich syntetycznych analogówStreszczenie: Przedstawiono przegląd aktualnych wyników badań dotyczących bioaktywnych oligomerów otrzymywanych z naturalnych alifatycznych ko-poliestrów (PHA) oraz ich syntetycznych analogów, uzyskanych na drodze anionowej polimeryzacji z otwarciem pierścienia (ROP) β-podstawionych β-laktonów. Omówiono ścieżki syntezy tych oligomerów opracowane głównie przez polskich badaczy. Zaprezentowane metody umożliwiają projektowanie nowych biodegradowalnych, a zarazem bioaktywnych oligomerów mogących znaleźć różnorodne zastosowania w medycynie, przemyśle kosmetycznym i agrochemii.Słowa kluczowe: poliester alifatyczny, anionowa polimeryzacja, oligomer bioaktywny, β-podstawiony β-lakton.

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Oligo-3-hydroxybutyrate functionalised pyrroles for preparation of biodegradable conductive polymers

Cited by 13 publications

References 43 publications

N‐Oligo(3‐hydroxybutyrate)‐functionalized polypyrroles: towards bio‐erodible conducting copolymers

N‐Oligo(3‐hydroxybutyrate)‐functionalized polypyrroles: towards bio‐erodible conducting copolymers

Aligned poly (glycolide‐lactide) fiber membranes with conducting polypyrrole

Bioactive oligomers from natural polyhydroxyalkanoates and their synthetic analogues

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