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Fluorinated building blocks for organic synthesis and macromolecule synthesis

Description:

Synthesis of trifluoromethylated alkylboron compounds and incorporation into small molecules and macromolecules

 

Inventor

Gary A. Molander, Hirschmann-Makineni Professor of Chemistry and Department Chair

 

Problem

Fluorinated macromolecules are widely utilized in industry, with the most notable example being Teflon, or perfluorotetrafluoroethylene (PTFE). Additionally, methods for incorporating CF3 into small organic molecules are not well developed, but are needed to expand the chemical repertoire for fluorine incorporation into pharmaceuticals, agrochemicals, and materials.

 

Solution

Researchers in the Molander laboratory have developed a metal-free synthetic route to incorporate CF3 groups and other fluorinated alkyl chains into small molecules as well as macromolecules using organoboron intermediates to generate newfound, polyfluorinated entities.  These organoboron building blocks are bench-stable, with indefinite shelf-life.  The synthetic methods developed allow the introduction of CF3 at sp3-hybridized centers via a novel carbon-carbon bond connection.

 

Advantages

•       Low surface tension and coefficient of friction

•       High chemical and thermal stability

•       More readily soluble than existing fluoropolymers

•       Excellent dielectric properties

•       Physical properties potentially superior to Teflon / PTFE

•       Biodegradability

 

Applications

•       Non-stick coatings

•       Lubricants

•       Surfactants

•       Wirings

•       Composites

•       Bench-stable, trifluoromethylated building blocks for pharmaceutical and agrochemical applications

 

 

Stage of Development

•       Proof-of-concept

 

Intellectual Property

UP application (US20160002270)

 

Reference Media

Ryu D. et al.  Chem. Eur. J., 2016, 22, p. 120-133.

Molander G.A. and Ryu D. Angew. Chemie, 2014, 53(51), p. 14181-14185.

Argintaru O.A. et al.  Angew. Chemie, 2013, 52(51), p. 13656-13660.

 

Desired partnerships

• License

Co-development

 

 

Download PDF

 

Docket #  Z6435 


Patent Information:
For Information, Contact:
Joshua Jeanson
Associate Director, SEAS/SAS Licensing Group
University of Pennsylvania
jeanson@upenn.edu
Inventors:
Gary Molander
Keywords: