Hydrogen‐bonding donor‐acceptor Stenhouse adducts

Neil Mallo , Arnaud Tron (1) , Joakim Andréasson , Lorrie Jacob , Jason Harper , Nathan Mcclenaghan (2) , Gediminas Jonusauskas (3) , Jonathon Edward Beves

1 CAM - University of Cambridge [UK]
2 ISM - Institut des Sciences Moléculaires
3 LOMA - Laboratoire Ondes et Matière d'Aquitaine

The binding of donor-acceptor Stenhouse adducts (DASAs) bearing hydrogenbond recognition groups by Hamilton-type receptors significantly influenced their photoswitching properties by altering thermal barriers to isomerization. The thermal barrier between the most stable linear isomer and the photo-generated isomer is lowered on binding to a receptor, and this barrier is crucial for switching properties. The thermal isomerization was shown to proceed via a stepwise linear-enol-keto mechanism in DMSO where the barrier to tautomerisation is within 2 kJ•mol-1 of that of the rate-determining step, which may be important for analyzing switching properties.

Domaines: Chimie-Physique [physics.chem-ph]; Optique [physics.optics]

Neil Mallo, Arnaud Tron, Joakim Andréasson, Lorrie Jacob, Jason Harper, et al.. Hydrogen‐bonding donor‐acceptor Stenhouse adducts. ChemPhotoChem, 2020, ⟨10.1002/cptc.201900295⟩. ⟨hal-02464386⟩