Metal-organic frameworks, abbreviated to MOFs, are porous materials built from organic ligands (as linkers) and metal cations or clusters (as nodes). MOFs can be designed to possess outstanding surface areas (up to 8000 m2 g-1) in addition to chemical and thermal stability. These materials have been proposed for multiple applications including gas storage and separation, light-emitting devices and sensors. When the organic linker is enantiopure, a chiral metal-organic framework is obtained instead. This unique approach to introduce chirality in these porous opens interesting opportunities for enantioselective processes such as asymmetric catalysis and chiral recognition.
TAMOF-1 is a highly porous, homochiral metal-organic framework built from a L-histidine derivative and Cu2+. This material has been the starting point of this thesis, in the search for plausible applications in chemical synthesis, catalysis and analysis. First, we optimised the synthesis of TAMOF-1 in terms of particle size, surface area (BET) and high-density, self-shaping monoliths. Next, we expanded its features by incorporation of nanoparticles into its porous structure, or by substitution with longer organic linkers with the aim of increasing the size and width of the porous network in a TAMOF-X family. Then, we investigated several applications of TAMOF-1. On one end, it is a heterogeneous catalyst able to promote kinetic resolution in epoxide opening reactions. On the other end, and taking advantage of its intrinsic chirality, we demonstrated the promising performance of TAMOF-1 as chiral stationary phase for the chromatographic separation of racemic mixtures. Furthermore, TAMOF-1 is also able to solve other mixtures of isomers, including positional isomers of aromatic compounds. These separations were carried out in HPLC conditions, demonstrating the high mechanical and structural stability of the material.
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