A high-yield synthesis and acid-base response of phosphate-templated rotaxanes
© 2016 The Royal Society of Chemistry. Anion-templated rotaxanes are a rare class of functional organic molecules capable of novel switching and mechanical behaviors. Yet, investigations of these properties are limited by existing synthetic strategies. We show a high-yielding synthesis (80%) of rotaxanes using shape-persistent macrocycles, cyanostars, and anionic organo-phosphate templates catalyzed by low steric-demand click chemistry. The reaction yields correlate with the template's binding affinities. Use of longer linkers relieves steric congestion to enable a reversible acid-base response, opening the way to molecular switching.
Publication Source (Journal or Book title)
Qiao, B., Liu, Y., Lee, S., Pink, M., & Flood, A. (2016). A high-yield synthesis and acid-base response of phosphate-templated rotaxanes. Chemical Communications, 52 (94), 13675-13678. https://doi.org/10.1039/c6cc08113d