cm6b03078_si_001.pdf (6.21 MB)
Covalent Functionalization of Carbon Nanomaterials with Iodonium Salts
journal contribution
posted on 2016-12-02, 21:14 authored by Maggie He, Timothy M. SwagerCovalent functionalization significantly
enhances the utility of
carbon nanomaterials for many applications. Herein, we report an efficient
method for the covalent functionalization of carbon nanotubes (CNTs)
and graphite. This reaction involves the reduction of carbon nanomaterials
with sodium naphthalide, followed by the addition of diaryliodonium
salts. CNTs, including single-walled, double-walled, and multi-walled
variants (SWCNTs, DWCNTs, and MWCNTs, respectively), as well as graphite,
can be efficiently functionalized with substituted arene and heteroarene
iodonium salts. The preferential transfer of phenyl groups containing
electron-withdrawing groups was demonstrated by reactions with unsymmetrical
iodonium salts. The lower reactivity of iodonium salts, relative to
the more commonly used diazonium ions, presents opportunities for
greater diversity in the selective functionalization of carbon nanomaterials.