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Structure-function Study of Poly(sulfobetaine 3,4-ethylenedioxythiophene) (PSBEDOT) and Its Derivatives

Structure-function Study of Poly(sulfobetaine 3,4-ethylenedioxythiophene) (PSBEDOT) and Its Derivatives

Chen-Jung Lee, Huifeng Wang, Megan Young, Shengxi Li, Fang Cheng, Hongbo Cong, Gang Cheng

Acta Biomater. 2018 Jul 15;75:161-170.

PMID: 29879552

Abstract:

Poly(3,4-ethylenedioxythiophene) (PEDOT) has been widely studied in recent decades due to its high stability, biocompatibility, low redox potential, moderate band gap, and optical transparency in its conducting state. However, for its long-term in vivo applications, the biocompatibility of PEDOT still needs to be improved. To address this challenge, zwitterionic poly(sulfobetaine 3,4-ethylenedioxythiophene) (PSBEDOT) that contains EDOT backbone with sulfobetaine functional side chains was developed in our previous study. Although PSBEDOT showed great resistance to proteins, cells, and bacteria, it is still not clear how the zwitterionic sulfobetaine side chain affects the electrochemical properties of the polymer and reactivity of the monomer. To achieve better understanding of the structure-function relationships of zwitterionic conducting polymers, we synthesized two derivatives of PSBEDOT, PSBEDOT-4 and PSBEDOT-5, by introducing the alkoxyl spacer between PEDOT backbone and sulfobetaine side chain. The interfacial impedance of PSBEDOT-4 and PSBEDOT-5 was examined by electrochemical impedance spectroscopy and showed significant improvement which is about 20 times lower than PSBEDOT on both gold and indium tin oxide substrates at 1 Hz. In the protein adsorption study, PSBEDOT, PSBEDOT-4 and PSBEDOT-5 exhibited comparable resistance to the fibrinogen solution. All three polymers had low protein adsorption around 3-5% comparing to PEDOT. Additionally, the morphology of PSBEDOT, PSBEDOT-4 and PSBEDOT-5 have been investigated by scanning electron microscopy. We believe that these stable and biocompatible materials can be excellent candidates for developing long-term bioelectronic devices.
Statement of significance:
To address the challenges associated with existing conducting polymers for bioelectronics, we developed a versatile and high performance zwitterionic conducting material platform with excellent stability, electrochemical, antifouling and controllable antimicrobial/antifouling properties. In this work, we developed two high-performance conducting polymers and systematically investigated how the structure affects their properties. Our study shows we can accurately tune the molecular structure of the monomer to improve the performance of zwitterionic conducting polymer. This zwitterionic conducting polymer platform may dramatically increase the performance and service life of bio-electrochemical devices for many long-term applications, such as implantable biosensing, tissue engineering, wound healing, robotic prostheses, biofuel cell etc., which all require high performance conducting materials with excellent antifouling property/biocompatibility at complex biointerfaces.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP126213501	3,4-Ethylenedioxythiophene		126213-50-1	Price

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