Tröger's Base-Embedded Pillararenes─Macrocycles with Both Fixed and Conformational Chirality.

Org Lett

Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.

Published: August 2024

Tröger's base-embedded pillararenes (), which combine Tröger's base () with dialkoxybenzene units, were prepared via a fragment-coupling macrocyclization strategy. The unit in macrocycle 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.

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http://dx.doi.org/10.1021/acs.orglett.4c02572DOI Listing

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