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Fluorinated building blocks for organic synthesis and macromolecule synthesis

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

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 Lab 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: 

Desired Partnerships: 

  • License
  • Co-development

Patent Information:

Inventors:

Gary Molander

Docket # Z6435

For Information, Contact:

Cortney Cavanaugh
Licensing Officer, SEAS/SAS Licensing Group
University of Pennsylvania
215-898-9591
ccav5@upenn.edu

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