Electrically conducting poly(pyrazoles)
Inventors
Martin, Brett D. • Giles, Ian D. • Naciri, Jawad • Charles, Paul T. • Trammell, Scott A. • Deschamps, Jeffrey R. • DePriest, Jeffrey C.
Assignees
Publication Number
US-11920035-B2
Publication Date
2024-03-05
Expiration Date
2038-12-12
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Abstract
This disclosure concerns electrically conducting poly(pyrazoles). The concept of oligomerizing and polymerizing substituted aminopyrazole derivatives combined with a monomer activation procedure involving base-mediated conversion of the protonated pyrazole ring nitrogen to amine salt was developed. This disclosure concerns the specific chemistries needed for the synthesis of a pyrazole monomer used in the polymer synthesis. The procedure used for blending the novel polypyrazoles with other compounds needed for construction of solar cells for testing was developed. This disclosure concerns the concept of using these types of heteroatom-rich, electron-deficient oligomers or polymers as n-dopable or p-dopable electron acceptors in photovoltaic cells. This disclosure concerns synthesizing the starting monomer compounds and polypyrazoles.
Core Innovation
This disclosure concerns electrically conducting poly(pyrazoles) developed by oligomerizing and polymerizing substituted aminopyrazole derivatives. The invention includes a monomer activation procedure involving base-mediated conversion of the protonated pyrazole ring nitrogen to an amine salt. Specific chemistries for synthesizing pyrazole monomers used in the polymer synthesis are detailed, along with procedures for blending these novel polypyrazoles with other compounds necessary for constructing solar cells for testing.
The concept of using heteroatom-rich, electron-deficient oligomers or polymers as n-dopable or p-dopable electron acceptors in photovoltaic cells is also taught. The invention enables the synthesis of starting monomer compounds and polypyrazoles, characterized by high electron transport rates, versatile redox behavior, and simple one-step synthesis using low-cost starting materials. These features facilitate efficient production and rapid investigation of derivatives.
The background emphasizes the need for renewable energy sources due to finite petroleum reserves. While silicon-based solar cells are efficient but expensive, polymer-based cells are less costly but often have low efficiencies and expensive polymers. This invention aims to provide polymers that increase solar cell efficiency while substantially reducing synthesis costs compared to commercially available solar cell polymers.
Claims Coverage
The patent contains a set of claims directed to poly(3-amino-4-nitropyrazole) compounds, with independent claims focused on the chemical structure and synthesis parameters.
Poly(3-amino-4-nitropyrazole) chemical composition
A poly(3-amino-4-nitropyrazole) compound represented by a specific chemical formula, defining its polymeric structure.
Synthesis conditions involving temperature and complex formation
A synthesis step where dissolving 4-nitro 3-aminopyrazole in solution occurs at 70° C., allowing a 1:1 molar complex formation between potassium and the deprotonated nitrogen of the pyrazole ring.
Use of sodium or potassium persulfate in polymerization
Adding sodium or potassium persulfate to the reaction mixture to achieve a final molar ratio of 1.2 moles persulfate per 1.0 moles 4-nitro-3-aminopyrazole, facilitating the polymerization process.
The independent claims focus on the novel poly(3-amino-4-nitropyrazole) polymer composition and its specific synthesis conditions including temperature, complex formation, and oxidant molar ratios, which define the inventive scope of the polymer and its production method.
Stated Advantages
Enables increases in solar cell efficiency compared to existing polymer solar cells.
Costs much less to synthesize than virtually all commercially available solar cell polymers.
High electron transport rates and versatile redox behavior facilitate effective electron donor and acceptor functions.
Simple one-step synthesis using low-cost starting materials allows easy and rapid production and investigation of derivatives.
Solar cells constructed with these polymers produce photocurrents up to 5.1 times higher and responsivities 2.9 to 70-fold higher than similar cells made with commercially available polymers.
Documented Applications
Use of electrically conducting poly(pyrazoles) as n-dopable or p-dopable electron acceptors in photovoltaic (solar) cells.
Incorporation into mostly-organic solar cells to improve light-harvesting ability and photocurrent generation.
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