Mechanochemical synthesis of an elusive fluorinated polyacetylene

Autor: Joseph A. H. Romaniuk, Noah Z. Burns, Jordan M. Cox, Carl M. F. Mansson, Yan Xia, Kurt P. Lindquist, Zexin Jin, Lynette Cegelski, Steven A. Lopez, Benjamin R. Boswell
Rok vydání: 2020
Předmět:
Zdroj: Nature Chemistry. 13:41-46
ISSN: 1755-4349
1755-4330
DOI: 10.1038/s41557-020-00608-8
Popis: Polymer mechanochemistry has traditionally been employed to study the effects of mechanical force on chemical bonds within a polymer backbone or to generate force-responsive materials. It is under-exploited for the scalable synthesis of wholly new materials by chemically transforming the polymers, especially products inaccessible by other means. Here we utilize polymer mechanochemistry to synthesize a fluorinated polyacetylene, a long-sought-after air-stable polyacetylene that has eluded synthesis by conventional means. We construct the monomer in four chemical steps on gram scale, which involves a rapid incorporation of fluorine atoms in an exotic photochemical cascade whose mechanism and exquisite stereoselectivity were informed by computation. After polymerization, force activation by ultrasonication produces a gold-coloured, semiconducting fluoropolymer. This work demonstrates that polymer mechanochemistry is a valuable synthetic tool for accessing materials on a preparative scale.
Databáze: OpenAIRE