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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
Published on: September 26, 2016
Synthesis of perfluoro[2.2]paracyclophane
William R Dolbier1, Puhui Xie, Lianhao Zhang
1Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, Florida 32611-7200, USA. wrd@chem.ufl.edu
The Journal of Organic Chemistry
|February 28, 2008
Summary
Researchers synthesized perfluoro[2.2]paracyclophane, a highly sought-after fluorinated aromatic compound. This achievement provides a new pathway for accessing complex fluorinated molecules.
Area of Science:
- Organic Chemistry
- Fluorine Chemistry
- Materials Science
Background:
- The synthesis of perfluoro[2.2]paracyclophane has been a long-standing goal in fluorine chemistry.
- Previous studies on partially fluorinated octafluoro[2.2]paracyclophane (AF4) highlighted the need for its fully fluorinated analog.
Purpose of the Study:
- To achieve the first successful synthesis of perfluoro[2.2]paracyclophane.
- To develop reliable synthetic routes for both the target compound and its key precursor.
Main Methods:
- The synthesis involved the reductive coupling of 1,4-bis(chlorodifluoromethyl)-2,3,5,6-tetrafluorobenzene using zinc in acetonitrile at 100°C.
- Two distinct preparations of the precursor were explored, including an improved method starting from 1,2,4,5-tetrachlorobenzene.
Main Results:
- Perfluoro[2.2]paracyclophane was successfully synthesized in a 39% yield.
- Efficient methods for preparing the necessary fluorinated precursor were established.
Conclusions:
- The study reports the first synthesis of perfluoro[2.2]paracyclophane, fulfilling a significant objective in organofluorine chemistry.
- The developed synthetic strategies offer valuable contributions to the field of fluorinated aromatic compounds.
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