Supramolecular chemistry involves the synthesis and analysis of supermolecules, chemical systems bound and arranged by noncovalent interactions. Within the scope of supramolecular chemistry, host-guest systems are studied for a variety of applications including, but not limited to, environmental remediation and pharmaceutical delivery. Using a pnictogen-assisted self-assembly technique taking advantage of the dynamic covalent chemistry of disulfide bonds, paired with a templating antimony molecule, our group investigates the synthesis of unique and novel macrocycles, for a range of applications with great focus on host-guest characterization and application. Due to their well-studied complexing capabilities, crown ethers presented an apt target for macrocyclization and subsequent macrocyclic host-guest studies. Despite the wide array of literature investigating crown ethers, few literature precedents described appending sulfide groups to typical crown ethers; additionally, no previous literature described the successful macrocyclization of a crown ether species. As a result, a variety of synthetic challenges (low selectivity, poor purifications, low yields) were encountered and addressed during the production of the desired crown ether compound. Using dibenzo-18-crown-6-ether, our group synthesized and identified a macrocycle composed of crown ether subunits. Further strengthened by the synthesis of this novel macrocycle, this synthetic approach showcases the robust and dynamic nature of pnictogen-assisted self-assembly.

Synthesis of a novel 18-crown-6-ether macrocycle

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