New materials for one-handed synthesis

Geoff Jameson with Shane Telfer (Massey University), affiliated with the MacDiarmid Institute for Advanced Materials and Nanotechnology (and colleagues)

Chirality in chemistry describes the "handedness" of a molecule, meaning it exists in two forms. These molecules, like left and right hands, cannot be perfectly aligned with their mirror images.

The effect of chirality can be benign, such as right-handed carvone smelling like spearmint and left-handed carvone smelling like caraway. In rare cases, it can be catastrophic such as when one version of thalidomide was effective for morning sickness, but the other caused birth defects in thousands of babies and an unknown number of miscarriages. 

The challenge

The chemical synthesis of just one version of a chiral molecule is extremely challenging and has relevance for many biologically relevant compounds.

The research

The research team designed metal-organic framework (MOF) materials containing two different interpenetrated (interlocking) components. One of these components can act as a catalyst, while the other component can promote the formation of one hand over the other.

The MOF structures were studied with single crystal X-ray diffraction on the Macromolecular Crystallography (MX2) beamline, to map and measure different levels of interpenetration at different locations on the crystal. 

The impact

This new way of rationally designing bi-functional MOF materials with unique properties was demonstrated in the catalytic synthesis of chiral chemicals.

The microfocus beam and tuneable energy range of the MX2 beamline was able to structurally characterise these complex materials and enable the creation of a design blueprint for the formation of interwoven frameworks with complimentary functionalities.

Reference:

Perl D, Lee SJ, Ferguson A, Jameson GB and Telfer SG. 2023. Hetero-interpenetrated metal–organic frameworks. Nature Chemistry 15:1358-1364. https://doi.org/10.1038/s41557-023-01277-z