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Mechanochemical Synthesis of Elusive Fluorinated Polyacetylene

preprint
submitted on 06.12.2019 and posted on 13.12.2019 by Benjamin R. Boswell, Carl M. F. Mansson, Jordan M Cox, Zexin Jin, Joseph A. H. Romaniuk, Kurt P. Lindquist, Lynette Cegelski, Yan Xia, Steven Lopez, Noah Z. Burns

Polymer mechanochemistry has traditionally been employed to study the effects of mechanical force on one or two chemical bonds within a polymer. It is underexploited for the scalable synthesis of wholly new materials by activating bonds along the entire polymer, especially products inaccessible by other means. Herein we utilize polymer mechanochemistry to synthesize fluorinated polyacetylene, a long-sought-after air-stable polyacetylene that has eluded synthesis by conventional means. Our synthetic approach proceeds via ultrasonication of a force-responsive precursor polymer that was synthesized in five steps on gram scale. The synthesis is highlighted by rapid incorporation of fluorine in an exotic photochemical cascade whose mechanism and exquisite diastereoselectivity were elucidated by computation.

Funding

DARPA-SN-18-47

N00014-17-S-F006

ECCS-1542152

History

Email Address of Submitting Author

nburns@stanford.edu

Institution

Stanford University

Country

United States

ORCID For Submitting Author

0000-0003-1064-4507

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version 1.0

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