A high-yield synthesis and acid-base response of phosphate-templated [3] rotaxanes

作者:Qiao Bo; Liu Yun; Lee Semin; Pink Maren; Flood Amar H
来源:Chemical communications, 2016, 52(94): 13675-13678.
DOI:10.1039/c6cc08113d

摘要

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 organophosphate 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.

  • 出版日期2016