Bioactive conducting scaffolds: Active ester-functionalized polyterthiophene

Lee, Jae Young; Jeong, Euh‐Duck; Ahn, Chang Won; Lee, Joo-Woon

doi:10.1016/j.synthmet.2013.09.044

Cited by 12 publications

(14 citation statements)

References 30 publications

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“…In the previous reports, terthiophene derivatives (i.e., 3'-substituted trimers of heterocyclic thiophene) exhibited lower oxidation potential, compared to thiophene derivatives (i.e., 3-substituted monomer of thiophene). [25][26][27] This led to high electrical conductivity and mechanical integrity of polymers from the terthiophene over the thiophene derivatives, attributed to alternate side chains that reduce steric interactions and structural irregularities. 28 Therefore, preferential bulk properties of PPy-N-MA (4) could be optimized by adding pristine pyrrole to the Py-N-MA (3) solution before the film was oxidized in the electrochemical reduction/re-oxidation (dedoping/doping) processes, finally leading to the copolymer, poly(pyrrole-co-(3)).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Methacrylate-Endcapped Conductive Polypyrrole as a Telechelic Polymer

Lee¹

2017

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This paper reports on the electrochemical synthesis of electrically conductive N-methacrylated polypyrrole as a unique telechelic polymer with highly reactive vinyl functionality, which can be further polymerized to prepare graft copolymers with low molecular weight typical monomers such as other (meth)acrylates, styrenes, (meth)acrylamides, and (meth)acrylonitriles using ionic, radical, and other specialized polymerization techniques. It is based on a new dual reactive monomer containing each methacrylate and pyrrole functionalities at each opposite end of the structure, 3-((3-(1H-pyrrol-1-yl)propanoyl)oxy)-2-hydroxypropyl methacrylate, whose synthesis is presented in this work.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Methacrylate-Endcapped Conductive Polypyrrole as a Telechelic Polymer

Lee¹

2017

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“…Various trimer carboxylic acids have been prepared, directly connected to the thiophene rings [ 342 , 343 , 344 , 345 ] or linked through a spacer. In fact, spacers of one [ 346 , 347 , 348 , 349 , 350 , 351 , 352 ], two [ 279 , 353 , 354 ], three [ 355 ], four [ 354 ], five [ 356 ] or six [ 350 ] carbon atoms are reported ( Scheme 18 , I and II).…”

Section: Trimer Structuresmentioning

confidence: 99%

Thiophene-Based Trimers and Their Bioapplications: An Overview

et al. 2021

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Certainly, the success of polythiophenes is due in the first place to their outstanding electronic properties and superior processability. Nevertheless, there are additional reasons that contribute to arouse the scientific interest around these materials. Among these, the large variety of chemical modifications that is possible to perform on the thiophene ring is a precious aspect. In particular, a turning point was marked by the diffusion of synthetic strategies for the preparation of terthiophenes: the vast richness of approaches today available for the easy customization of these structures allows the finetuning of their chemical, physical, and optical properties. Therefore, terthiophene derivatives have become an extremely versatile class of compounds both for direct application or for the preparation of electronic functional polymers. Moreover, their biocompatibility and ease of functionalization make them appealing for biology and medical research, as it testifies to the blossoming of studies in these fields in which they are involved. It is thus with the willingness to guide the reader through all the possibilities offered by these structures that this review elucidates the synthetic methods and describes the full chemical variety of terthiophenes and their derivatives. In the final part, an in-depth presentation of their numerous bioapplications intends to provide a complete picture of the state of the art.

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“…[11,96] In particular, functionalizing a surface with the RGD peptide makes it possible for cells to adhere without presence of serum in the culture media. [97] Many of the commonly used conjugated polymers lack available groups for covalent attachment of functional groups though. However, proteins and other biomolecules of interest can be incorporated as counter ions during electropolymerisation (see section 5.2.2), as they often carry negatively charged groups.…”

Section: Cell Adhesionmentioning

confidence: 99%

Electronic Control of Cell Cultures Using Conjugated Polymer Surfaces

Persson¹

2014

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In the field of bioelectronics various electronic materials and devices are used in combination with biological systems in order to create novel applications within cell biology and medicine. A famous example of a successful bioelectronics application is the pacemaker. Metals are the most common electrical conductors, whereas polymers are generally considered being insulators. However, in the late 1970s it was shown that a special class of polymers with conjugated double bonds, could in fact, after some chemical modifications, conduct electricity. This was the start of the research field known as conducting polymers, and then later on organic electronics, a research area that has grown rapidly during the last decades. Conjugated polymers are also suitable to interact and interface with cells and tissues, as they are generally soft, flexible and biocompatible. In addition, their chemical properties can be tailor-made through synthesis to fit biological requirements and functions. During the last years applications using organic bioelectronics have become numerous. This thesis describes applications based on different conjugated polymers aiming to stimulate and control cell cultures. When culturing cells it is of interest to be able to control events such as adhesion, spreading, proliferation, differentiation and detachment. First, the impact of different polymer compositions and redox states on the adhesion of bacteria and subsequent biofilm formation was investigated. Similar polymer electrodes were also used to steer differentiation of neural stem cells, through changes in the surface exposure of a relevant biomolecule. Controlled delivery of molecules was achieved by coating nanoporous membranes with polymers that swell and contract when changing the redox state. Finally, electronic control over cell detachment using a water-soluble polymer was achieved. When applying a positive potential to this polymer, it swells, cracks and finally detaches, taking the cells that was cultured on top along with it. Together, the work and results presented in this thesis demonstrate a versatile conjugated polymer technology to achieve electronic control of the different growth stages of cell cultures as well as cellular functions. POPULÄRVETENSKAPLIG SAMMANFATTNINGOlika plaster finns numera överallt omkring oss och utgör ett av de absolut vanligaste materialen i vår vardag. Även elektronik har blivit en naturlig del av vår tillvaro och finns i en mängd olika produkter. Inom medicinsk teknik kommer allt fler applikationer som innefattar elektronik, ett exempel är pacemakern. Arbetet som ligger till grund för denna avhandling strävar efter att kombinera plaster och elektronik för tillämpningar inom medicin och cellbiologi.Plaster består till största delen av polymerer samt olika tillsatser för att få ett material med önskade egenskaper. Polymerer är i sin tur uppbyggda av långa kedjor av identiska molekylära byggstenar, så kallade monomerer. Monomerens kemi och struktur bestämmer även egenskaperna hos polymeren. Med hjä...

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Bioactive conducting scaffolds: Active ester-functionalized polyterthiophene

Cited by 12 publications

References 30 publications

Synthesis of Methacrylate-Endcapped Conductive Polypyrrole as a Telechelic Polymer

Synthesis of Methacrylate-Endcapped Conductive Polypyrrole as a Telechelic Polymer

Thiophene-Based Trimers and Their Bioapplications: An Overview

Electronic Control of Cell Cultures Using Conjugated Polymer Surfaces

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