A high-yield synthesis and acid–base response of phosphate-templated [3]rotaxanes. Issue 94 (4th November 2016)

• Record Type: Journal Article
• Authors: Qiao, Bo; Liu, Yun; Lee, Semin; Pink, Maren; Flood, Amar H.
• Is Part Of: Chemical communications. Volume 52:Issue 94(2016)
• Page Start: 13675
• Page End: 13678
• Publication Date: 2016-11-04
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc08113d
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : We show a high-yielding synthesis (80%) of [3]rotaxanes using shape-persistent macrocycles, cyanostars, and anionic organo-phosphate templates catalyzed by low steric-demand click chemistry. Abstract : 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 [3]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.