Main Group Supramolecular Chemistry Led to Surprising New Directions in the Self-Assembly of Organic Macrocycles, Cages, and Cyclophanes

Abstract

AbstractCyclophanes are an admirable class of macrocyclic and cage compounds that often display unusual properties due to their high strain and unusual conformations. However, the exploration of new, complex cyclophanes has been encumbered by syntheses that can be low yielding, require harsh reaction conditions, and arduous purification steps. Herein, we discuss our work using metalloid-directed self-assembly and dynamic covalent chemistry to form cryptands. These were then subjected to mild conditions to produce discrete disulfide, thioether and hydrocarbon macrocycles in high yields. ‘Design of Experiments’ was then used to selectively synthesize targeted macrocycles from complex mixtures.1 Introduction2 Cryptands to Cyclophanes3 Functionalizable Macrocycles4 ‘Design of Experiments’ Targeted Synthesis5 Conclusions and Outlook