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Download fileSynthesis of 2D Imine-Linked Covalent Organic Frameworks through Formal Transimination Reactions
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posted on 2017-08-30, 00:00 authored by Edon Vitaku, William R. DichtelCovalent organic
frameworks (COFs) are crystalline, permanently
porous, two-dimensional or three-dimensional polymers with tunable
topology and functionality. COFs linked with imines or β-ketoenamines
are more chemically stable than their boron-linked counterparts, making
them more promising for a broad range of applications, including energy
storage devices, proton-conductive membranes, and catalyst supports.
We report a general and scalable method for synthesizing imine- and
β-ketoenamine-linked COFs based on the formal transimination
of N-aryl benzophenone imines. These substrates are
often the synthetic precursors of traditional polyfunctional aryl
amine monomers and are more stable, soluble, and easy to handle and
purify. The imine- and β-ketoenamine-linked COFs obtained from
this approach show excellent materials quality, as characterized by
X-ray diffraction and surface area analysis. The most optimized COF
exhibited a Brunauer–Emmett–Teller surface area (>2600
m2/g) very close to its theoretical value (2830 m2/g). This method is amenable to both conventional solvothermal conditions
and microwave heating, providing similar or even improved materials
quality with shorter reaction times. The high materials quality, scalability,
and availability of benzophenone imine monomers are all attractive
features of this approach.