A structural study into halogenated derivatives of mandelic acid as building blocks of chiral coordination polymers

Abstract

Mandelic acid and its derivatives are an excellent source of chirality for the construction of chiral coordination polymers (CPs) and metal-organic frameworks (MOFs) for enantioselective applications. To date, limited reports exist for the incorporation of mandelic acid derivatives with halogen substituents such as fluorine and chlorine despite the extra intermolecular interactions possible. The extra sites for hydrogen and halogen bonding in these mandelic acid derivatives may afford interesting modes of coordination and packing in 3 D space. Six CPs containing mandelic acid and its halogenated analogues, (R)-2-chloromandelic acid, 3,5-difluoromandelic acid, 4-trifluoromethylmandelic acid, together with linear dipyridyl co-ligands are reported. These structures consist of three 2 D sql sheets and three 1 D chains with a range of packing motifs influenced by the differing intermolecular interactions present.

Graphical Abstract

Keywords:

• Chirality
• coordination polymers
• mandelic acid
• crystal engineering
• 1D chains
• 2D sheets
• supramolecular chemistry

Acknowledgments

C. H. gratefully acknowledges the University of Melbourne for a McKenzie Fellowship. This research was undertaken in part using the MX1 and MX2 beamlines at the Australian Synchrotron, part of ANSTO, and made use of the Australian Cancer Research Foundation (ACRF) detector.

Disclosure statement

No potential conflict of interest was reported by the authors.