Mechanical Reversibility of Strain-Promoted Azide-Alkyne Cycloaddition Reactions

Angewandte Chemie
Monique J JacobsKerstin G Blank

Abstract

Mechanophores, that is, molecules that show a defined response to force, are crucial building blocks of mechanoresponsive materials. The possibility of mechanically induced cycloreversion for a series of triazoles formed via strain-promoted azide-alkyne cycloaddition reactions was investigated by density functional theory calculations, and these triazoles were compared to the 1,4- and 1,5-regioisomers formed in the reaction of an azide with a terminal alkyne. We show that cycloreversion is in principal possible and that the pulling geometry is the most important parameter that determines the probability of cycloreversion. We further compared triazole stability to the mechanical stability of polymers that are frequently used as force transducers in mechanochemical experiments and identified DIBAC (azadibenzylcyclooctyne) as a promising mechanophore for future applications.

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Citations

Sep 13, 2016·Journal of the American Chemical Society·Maxwell J RobbJeffrey S Moore
Oct 22, 2016·Chemical Reviews·Tim Stauch, Andreas Dreuw
Mar 25, 2017·The Journal of Physical Chemistry. a·Wolfgang QuappJordi Ribas-Ariño
Jul 15, 2016·Chemistry : a European Journal·Michael F PillMartin K Beyer
Sep 24, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Lennart Jonathan MierTim Stauch
Jan 23, 2021·Journal of the American Chemical Society·Anton O RazgoniaevKatherine J Franz
May 15, 2021·Advanced Healthcare Materials·Muhammad RizwanMolly S Shoichet
Sep 23, 2020·Journal of the American Chemical Society·Liqi WangRoss A Widenhoefer
Sep 10, 2020·Journal of the American Chemical Society·Isabel M KleinMaxwell J Robb

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