Innovative, Fully Redox-Active Monomers and Polymers with Broad Applications (Case 1702)

Principal Investigator:

Tayhas Palmore, PhD, Professor
School of Engineering
Brown University
Providence, RI

Brief Description:

Interest in redox-active polymers stems from their application in electrochromic devices, biofuel cells, and biosensors all of which require a high concentration of electron mediators that are non-leachable.  The molecule 2,2’-azinobis-(3-ethylbenzothiazoline-6-sulfonate) or ABTS is an important redox-active compound with broad chemical, material and biomedical applications.  ABTS and derivatives have been used as the electrochromic compound in smart windows, as a chromogenic substrate in assays for enzymatic activity, and as a mediator for electron transfer in bioelectrocatalysis.  A focus on ABTS in the bioelectrocatalytic reduction oxygen to water has increased primarily because its redox potential is near that of oxygen under mildly acidic conditions; however, employment of ABTS/derivatives has been limited to solution phase applications.  The development and synthesis of polymerizable derivatives of ABTS would enable the fabrication of composites that possess redox and chromogenic properties of ABTS, but in a non-leachable, solid-phase form.  Use of current ABTS versions in composites leads to leaching of the ABTS molecule from the composite upon exposure to solvents.  This results in loss of the composite’s redox and chromogenic properties.

The invention is a proprietary method to create and apply fully redox-active monomers, polymers and co-polymers that involve the chemical synthesis of a novel redox-active monomer to address the limitations of the current state-of-the-art for improved commercial applications.  Thus, these monomers and polymers can be synthesized in a non-leachable, immobilized, solid-phase form, and be electrically conductive or not.  Compounds can be polymerized or co-polymerized with other monomers with various functional groups to tune the physical properties of the polymers.  To accommodate different applications, for example, a conductive polymer can be utilized to significantly increase current flow and stored energy in a polymer matrix, and polymers can be created that are used at low or high potentials.  Also, this invention describes and provides devices comprising one or more of these monomers and/or polymers for use in a wide variety of chemical, material and biomedical applications.  Biological molecules or other compounds can be coupled to the monomer/polymer such as enzymes, DNA, RNA, proteins, carbohydrates, lipids, pharmaceuticals, dyes, redox-active compounds.

Broadly, commercial applications for these novel monomers, polymers and co-polymers include a myriad of enzyme assays, handheld or other biosensors – detection in solution or air –, energy storage systems – battery or capacitor –, and electrochromic devices.  Specifically, some applications include: as the active components of a redox-active, chromogenic composite in the cathode of a biofuel or gas phase cell (humidified air or oxygen), electron mediator of an air-breathing biocathode, sensing element of a device to test for the presence of laccase or organisms that produce laccase – an enzyme indicative of contaminated wine or wine products, sensing element of a device to measure the presence of oxygen or pH of a solution, and display technologies that use suspended particle devices.  Several markets are indicated: wine production/vineyards; food/other beverage production/testing; drug/water/air testing; infectious disease diagnostics; electronics; energy (storage, biofuel cells); biosensors (medical or environmental) for air, water, wine, food bodily fluids; scientific R&D to advance the fields of material science, chemistry and biomedical diagnostics.

Information:

US patent 7,838,687 is issued (11/23/2010)
US patent 8,435,696 is issued (05/07/2013)

Patent Information:
For Information, Contact:
Margaret Shabashevich,
Manager of Operations
Technology Ventures Office
Brown University
401-863-7499 TVO_Patents@brown.edu
Inventors:
Tayhas Palmore
Hyun-Kon Song
Keywords:
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