Single-Molecule Observation of a Mechanically Activated Cis-to-Trans Cyclopropane Isomerization.

Journal Article

The mechanochemical activation of cis-gem-difluorocyclopropane (cis-gDFC) mechanophore in toluene was characterized with single-molecule force spectroscopy. Unlike previously reported behavior in methyl benzoate (MB), two transitions are observed in the force vs extension curves of cis-gDFC polymers in toluene. The first transition occurs at the same force of ∼1300 pN observed previously in MB, but a second transition is observed at forces of ∼1800 pN that reveal the partial formation of the trans-gDFC isomer. The behavior is attributed to competing reactions of the cis-gDFC at the 1300 pN plateau: addition of oxygen to a ring-opened diradicaloid intermediate, and isomerization of cis-gDFC to its trans isomer.

Full Text

Duke Authors

Cited Authors

  • Wang, J; Kouznetsova, TB; Craig, SL

Published Date

  • August 8, 2016

Published In

Volume / Issue

  • 138 / 33

Start / End Page

  • 10410 - 10412

PubMed ID

  • 27500711

Electronic International Standard Serial Number (EISSN)

  • 1520-5126

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/jacs.6b06452

Language

  • eng