Functionalized Polythiophene Copolymers for Electronic Biomedical Devices
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MRS Advances © 2020 Materials Research Society DOI: 10.1557/adv.2020.3
Functionalized Polythiophene Copolymers for Electronic Biomedical Devices Samadhan Nagane, Peter Sitarik, Yuhang Wu, Quintin Baugh, Shrirang Chhatre, Junghyun Lee, and David C. Martin Department of Materials Science and Engineering, The University of Delaware, Newark, DE 19716
ABSTRACT We continue to investigate the design, synthesis, and characterization of electrically and ionically active conjugated polythiophene copolymers for integrating a variety of biomedical devices with living tissue. This paper will describe some of our most recent results, including the development of several new monomers that can tailor the surface chemistry, adhesion, and biointegration of these materials with neural cells. Our efforts have focused on copolymers of 3,4 ethylenedioxythiophene (EDOT), functionalized variants of EDOT (including EDOT-acid and the trifunctional EPh), and dopamine (DOPA). The resulting PEDOT-based copolymers have electrical, optical, mechanical, and adhesive properties that can be precisely tailored by fine tuning the chemical composition and structure. Here we present results on EDOTdopamine bifunctional monomers and their corresponding polymers. We discuss the design and synthesis of an EDOT-cholesterol that combines the thiophene with a biological moiety known to exhibit surface-active behaviour. We will also introduce EDOT-aldehyde and EDOT-maleimide monomers and show how they can be used as the starting point for a wide variety of functionalized monomers and polymers.
INTRODUCTION: Functionalized polythiophene copolymers based on alkyl-dithiophenes, particularly poly(3,4-ethylene dioxythiophene) (PEDOT) and poly(3,4-propylene dioxythiophene) (PProDOT), have shown considerable interest for electronic biomedical devices, organic photovoltaics, and chemical sensors [1][2]. PEDOT and PProDOT copolymers have excellent mechanical properties, thermal stability, and chemical stability, making them attractive for use in these applications. PEDOT doped with poly(4-styrene sulfonate) (PSS) is commercially available in a processable aqueous suspension for fabricating organic electronic devices at relatively large scale. We typically use electrochemical polymerization to deposit these materials directly onto a conducting electrode, making it possible to precisely control the process [3–4].
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While PEDOT has shown considerable potential for these various applications, the polymer is relatively hydrophobic, and can show issues with relatively poor adhesion to solid surfaces. It also does not have any specific functionality for optimizing interactions with living tissue. This leads to issues in long-term performance, due to the possibility of cracking or delamination of the film, and unfavourable interactions wit
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