Tröger’s Base-Embedded PillararenesMacrocycles with Both Fixed and Conformational Chirality

Tröger’s base-embedded pillararenes (<b>P[1]TB[3]A</b>), which combine Tröger’s base (<b>TB</b>) with dialkoxybenzene units, were prepared via a fragment-coupling macrocyclization strategy. The <b>TB</b> unit in macrocycle <b>P[1]TB[3]A</b> provides a fixed chiral source, while 1,4-alkoxybenzene segments flip quickly to change their arrangement, which could provide reversible conformational chirality for those macrocycles. This rare example of macrocycles holding both fixed and conformational chirality lays a good foundation for expanding pillararenes using the fixed chiral source.