A high-yield synthesis and acid-base response of phosphate-templated [3]rotaxanes.
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.
Department of Chemistry, Indiana University, 800 E Kirkwood Ave., Bloomington, IN 47405, USA. aflood@indiana.edu.
Bo
B
Qiao
Department of Chemistry, Indiana University, 800 E Kirkwood Ave., Bloomington, IN 47405, USA. aflood@indiana.edu.
Yun
Y
Liu
Department of Chemistry, Indiana University, 800 E Kirkwood Ave., Bloomington, IN 47405, USA. aflood@indiana.edu and Beckman Institute for Advanced Science and Technology, University of Illinois at Urbana-Champaign, 405 North Mathews Avenue, Urbana, IL 61801, USA.
Semin
S
Lee
Department of Chemistry, Indiana University, 800 E Kirkwood Ave., Bloomington, IN 47405, USA. aflood@indiana.edu.
Maren
M
Pink
Department of Chemistry, Indiana University, 800 E Kirkwood Ave., Bloomington, IN 47405, USA. aflood@indiana.edu.
Amar H
AH
Flood