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Hydrogen‐Bonding Donor‐Acceptor Stenhouse Adducts
Author(s) -
Mallo Neil,
Tron Arnaud,
Andréasson Joakim,
Harper Jason B.,
Jacob Lorrie S. D.,
McClenaghan Nathan D.,
Jonusauskas Gediminas,
Beves Jonathon E.
Publication year - 2020
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201900295
Subject(s) - isomerization , adduct , hydrogen bond , chemistry , acceptor , photochemistry , thermal stability , enol , molecule , catalysis , organic chemistry , physics , condensed matter physics
The binding of donor‐acceptor Stenhouse adducts (DASAs) bearing hydrogen‐bond 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 photogenerated 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 tautomerisation barrier is within 2 kJ ⋅ mol −1 of that of the rate‐determining step, which may be important for analyzing switching properties.