A series of 2D imine-based covalent organic frameworks (COFs) were designed and synthesized having varying degrees of strategic fluorination. The dynamic equilibrium governing COF formation was dramatically impacted by the placement of fluorine atoms in the different monomers. Furthermore, in COFs where phenyl and perfluorophenyl units could seamlessly alternate between layers of the framework, self-complimentary π-stacking interactions dramatically improved both the crystallinity and the surface area of the material relative to non-fluorinated and highly fluorinated COFs. Transmission electron microscopy images also revealed more long-range order in COFs with alternating phenyl/perfluorophenyl stacking interactions. The results highlight a promising approach for improving surface areas and long-range order in 2D COFs. Their application as hydrogen storage materials will be discussed.

Complimentary π-stacking interactions for enhanced long-range order in 2D covalent organic frameworks

256th National Meeting (2018)

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