High-temperature
linear fluoropyridyl silicone-based oils and network
elastomers were prepared via hydrosilylation with multifunctional
perfluoropyridine (PFP)-based monomers possessing terminally reactive
alkenes. Monomers with varying degrees of functionalization were prepared
in a scalable manner and in high purity via the facile, regio-selective,
nucleophilic aromatic substitution (SNAr) of PFP in good
isolated yields. These multi-reactive monomers were polymerized via
Pt-catalyzed hydrosilylation with hydride-terminated polydimethylsiloxanes
(H-PDMSs) possessing varying degrees of polymerization and cross-linked
with the highly functionalized octadimethylhydrosilyl cubic siloxane.
These resulting polymers of varying architecture possessed exceptional
thermal stability with no onset of degradation up to 430 °C and
char yields as high as 62%, under inert pyrolysis conditions when
modified with cubic siloxane. Furthermore, by nature of the aliphatic
or aromatic content, programmable glass transition temperatures were
achieved from these elastomeric materials. Finally, the linear 3,5,6-fluoropyridine
PDMS systems demonstrated the ability to undergo regio-controlled
post-functionalization via SNAr with 4-bromophenol, allowing
access to silicone oils with potentially tailorable properties for
desired applications.
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