Pinpointing mechanochemical bond rupture by embedding the mechanophore into a macrocycle

Doreen Schütze; Katharina Holz; Julian Müller; Martin K Beyer; Ulrich Lüning; Bernd Hartke

doi:10.1002/anie.201409691

Pinpointing mechanochemical bond rupture by embedding the mechanophore into a macrocycle

Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2556-9. doi: 10.1002/anie.201409691. Epub 2015 Jan 22.

Authors

Doreen Schütze¹, Katharina Holz, Julian Müller, Martin K Beyer, Ulrich Lüning, Bernd Hartke

Affiliation

¹ Institut für Physikalische Chemie, Christian-Albrechts-Universität zu Kiel, Olshausenstraße 40, 24098 Kiel (Germany) http://ravel.pctc.uni-kiel.de/

PMID: 25613672
DOI: 10.1002/anie.201409691

Abstract

Mechanophores contain a mechanically labile bond that can be broken by an external mechanical force. Quantitative measurement and control of the applied force is possible through atomic force microscopy (AFM). A macrocycle was synthesized that contains both the mechanophore and an aliphatic chain that acts as a "safety line" upon bond breaking. This ring-opening mechanophore unit is linked to poly(ethylene glycol) spacers, which allow investigation by single molecule force spectroscopy. The length increase upon rupture of the mechanophore was measured and compared with quantum chemical calculations.

Keywords: DFT calculations; cycloreversion; macrocycles; mechanophores; single-molecule force spectroscopy.