Synthesis of Hetero-bifunctional, End-Capped Oligo-EDOT Derivatives

Spicer, Christopher D.; Booth, Marsilea A.; Mawad, Damia; Armgarth, Astrid; Nielsen, Christian B.; Stevens, Molly M.

doi:10.1016/j.chempr.2016.12.003

Cited by 26 publications

(31 citation statements)

References 51 publications

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“…Despite its favorable characteristics, PEDOT:PSS has one major drawback, that is, the difficulty to tailor the polymer and add a functionality to meet the needs of a particular application . Synthetic efforts have thus focused on routes to develop EDOT derivatives that carry the functionality required for the intended application such as biochemical sensing, interfacing with living systems , electrochromism, and energy storage . Chemical oxidative polymerization enabled bulk production of PEDOT based CPs furnished with various functionalities coexisting with conductivity, however, the chemistry behind is not easily adaptable, limiting their wide spread use.…”

Section: Methodsmentioning

confidence: 99%

In Situ Electrochemical Synthesis of a Conducting Polymer Composite for Multimetabolite Sensing

Wustoni

Hidalgo

Hama

et al. 2019

Adv Materials Technologies

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Electrochemical polymerization is a versatile method for rapid deposition of conducting polymer (CP) films. The target substrates have, however, been limited to planar, metallic surfaces; hence, the devices that integrate electropolymerized CP films have predominantly been passive electrodes. In this work, it is shown that electrochemical polymerization has a high degree of freedom, which allows growing biofunctionalized CP films in microscale transistor channels. CP films are electrochemically deposited from two monomers, namely, 3,4‐ethylenedioxythiophene (EDOT) and hydroxymethyl EDOT (EDOTOH), inside the channel of an organic electrochemical transistor (OECT). In aqueous electrolytes, the copolymer p(EDOT‐ran‐EDOTOH) shows excellent charging capability and OECT performance. The presence of hydroxyl groups facilitates stable incorporation of catalytic enzymes in the copolymer matrix during electropolymerization, rendering OECT channels biologically functionalized. The transistor channels made of CP films with the entrapped enzyme show output characteristics that change with respect to the concentration of its target metabolite. In the form of a miniaturized, single chip, the multi‐transistor platform simultaneously measures glucose, cholesterol, and lactate concentrations of a given fluid. With the ability to grow and pattern CPs functionalized with biorecognition units on miniaturized areas, this technique promises for the development of multiplexed platforms for electronic biosensing.

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Section: Methodsmentioning

confidence: 99%

In Situ Electrochemical Synthesis of a Conducting Polymer Composite for Multimetabolite Sensing

Wustoni

Hidalgo

Hama

et al. 2019

Adv Materials Technologies

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“…Although, oligoaniline (trimer, tetramer, pentamer) is a better substitute of PANI itself in terms of biocompatibility, solubility and processability, but both the materials have harmful effect on cells for long-term in vivo studies. To address this point, Spicer et al [71] developed a series of oligomers of EDOT for tissue engineering purposes.…”

Section: Covalent Grafting Of Conducting Polymersmentioning

confidence: 99%

Conducting Polymer Grafting: Recent and Key Developments

Maity

Dawn

2020

Polymers

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Since the discovery of conductive polyacetylene, conductive electroactive polymers are at the focal point of technology generation and biocommunication materials. The reasons why this research never stops growing, are twofold: first, the demands from the advanced technology towards more sophistication, precision, durability, processability and cost-effectiveness; and second, the shaping of conducting polymer research in accordance with the above demand. One of the major challenges in conducting polymer research is addressing the processability issue without sacrificing the electroactive properties. Therefore, new synthetic designs and use of post-modification techniques become crucial than ever. This quest is not only advancing the field but also giving birth of new hybrid materials integrating merits of multiple functional motifs. The present review article is an attempt to discuss the recent progress in conducting polymer grafting, which is not entirely new, but relatively lesser developed area for this class of polymers to fine-tune their physicochemical properties. Apart from conventional covalent grafting techniques, non-covalent approach, which is relatively new but has worth creation potential, will also be discussed. The aim is to bring together novel molecular designs and strategies to stimulate the existing conducting polymer synthesis methodologies in order to enrich its fascinating chemistry dedicated toward real-life applications.

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“…For biomedical applications, it supposed to have a deleterious effect when exposed to cells for a long period, either for biocompatibility or electrical stability (Meng et al, 2008;Green et al, 2012;Mawad et al, 2016). At this point, in 2017 Stevens et al (Spicer et al, 2017) proposed a series of conjugated oligomers of EDOT as an interesting alternative to oligoanilines for tissue engineering.…”

Section: Electroactive and Biodegradable Oligomers For Block Copolymersmentioning

confidence: 99%

Advances in Conducting, Biodegradable and Biocompatible Copolymers for Biomedical Applications

Silva

Torresi

2019

Front. Mater.

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Electroactive biomaterials are a new generation of "smart" biomaterials based on intrinsically conducting polymers (ICP). Among them, poly(3,4-ethylenedioxythiophene) (PEDOT), polypyrrole (PPy) and polyaniline (PANI) are well known conducting polymers that present excellent electrical and optical properties emerging as main candidates for potential biomedical applications. Additionally, the biodegradability of biomaterials is very useful and desirable. In this context, biodegradable polymers based on polyesters, such as poly(D,L-lactic acid) (PDLLA), polycaprolactone (PCL), and poly(glycolic acid) (PGA) appear to be promising candidates because of their good biocompatibility and, as a consequence, they have been attracting attention as sustainable alternatives for applications in medicine. Weak molecular interaction with cells, biocompatibility, biodegradability, mechanics and topography are some of the main challenges for the use of conducting polymers as biomaterials. In order to improve their own biocompatibility, the main strategies are whether by doping with specific counter ions (biodopants) or chemically modifying the monomers with different molecules. Although conventional ICPs still present low or none biodegradability, there are relatively few examples of biodegradable electroactive polymers in the literature. Recently, novel approaches have been applied to solve the problem of lack of biodegradability of conducting polymers, mainly through (1) synthesis of a modified electroactive oligomers connected via degradable ester linkages creating block copolymers and (2) synthesis of modified electroactive and biodegradable macromonomers based on polyesters used in a second step copolymerization with conductive monomers. This mini-review focuses on developing trends, challenges and summarizes the recent advances on synthesis of conducting, biodegradable and biocompatible copolymers in terms of optimizing the chemical properties to improved response toward different cells, aiming biomedical applications.

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Synthesis of Hetero-bifunctional, End-Capped Oligo-EDOT Derivatives

Cited by 26 publications

References 51 publications

In Situ Electrochemical Synthesis of a Conducting Polymer Composite for Multimetabolite Sensing

In Situ Electrochemical Synthesis of a Conducting Polymer Composite for Multimetabolite Sensing

Conducting Polymer Grafting: Recent and Key Developments

Advances in Conducting, Biodegradable and Biocompatible Copolymers for Biomedical Applications

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