Scientists have developed an innovative approach to incorporate harmful perfluoroalkenes into N-heterocyclic carbene ligands.
Commonly known as “forever chemicals,” PFAS (Perfluoroalkyl and Polyfluoroalkyl Substances) are notorious for their persistence in both the environment and our bodies. However, chemists from Osaka Metropolitan University have developed a simple yet innovative technique that can transform these harmful substances into valuable compounds.
Breakthrough in PFAS Conversion
A research group led by Professor Masato Ohashi and Assistant Professor Kenichi Michigami of the Graduate School of Science at Osaka Metropolitan University has successfully synthesized ligands called fluorine-decorated N-heterocyclic carbenes (NHCs) from perfluoroalkenes, a type of PFAS (Perfluoroalkyl and Polyfluoroalkyl Substances).
The NHCs developed in this study play significant roles in stabilizing unstable molecules as well as enhancing the performance of their ligated transition metal complexes.
The Process of Synthesis
The synthesis of fluorinated NHCs was achieved simply by removing two fluorine atoms from 1,2-difluoroalkene derivatives. Owing to the small size of fluorine atoms, the electron-accepting ability of the NHC ligand can be enhanced without substantially changing its steric properties.
“Our results enable the easy transformation of harmful PFAS into functional NHCs,” explained Dr. Michigami. “The versatile applications of fluorinated NHCs show potential advantages in various fields such as fluorine chemistry, organometallic chemistry, catalysis chemistry, and materials science.”
Reference: “N-Heterocyclic Carbenes with Polyfluorinated Groups at the 4- and 5-Positions from [3 + 2] Cycloadditions between Formamidinates and cis-1,2-Difluoroalkene Derivatives” by Masato Ohashi, Kota Ando, Shoichi Murakami, Kenichi Michigami and Sensuke Ogoshi, 26 September 2023, Journal of the American Chemical Society.
DOI: 10.1021/jacs.3c06331
The study was funded by the Japan Society for the Promotion of Science and the Japan Ministry of Education, Culture, Sports, Science and Technology (MEXT).
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1 Comment
I question the use of the prefix “per” when naming fluoroalkenes, because “perfluoro” implies total substitution of fluorine on the parent molecule, yet alkenes can undergo many addition reactions which open the double bond and add 2 more substituents. However, this is very useful chemistry and may present yet another path to remediating PFAS pollution. My comment concerns nomenclature, not novelty nor purpose.