Abstract
The mechanisms of three photodegradation reactions of 3-hydroxyflavone – its photosensitized oxygenation, photooxygenation with 3O2 and photorearrangement into an indanedione derivative – have been investigated by computing the free energy profiles.
Highlights
The photooxygenation of 3-hydroxyflavone (3HF) into O-benzoyl salicylic acid and the photorearrangement of 3HF into 3-hydroxy-3-phenyl-indane-1,2-dione have been studied using theoretical calculations
The results suggested the occurrence of an intermediate with a 1-indanone skeleton, formed through a transition state with a relatively high free energy barrier corresponding to the folding of the pyrone ring
We do not discuss the excited state intramolecular proton transfer (ESIPT) of 3HF in more detail, as it has been the subject of thorough theoretical works.[42,43,44,45]
Summary
The photooxygenation of 3-hydroxyflavone (3HF) into O-benzoyl salicylic acid and the photorearrangement of 3HF into 3-hydroxy-3-phenyl-indane-1,2-dione have been studied using theoretical calculations. These are the main photodegradation reactions of this versatile fluorescent probe which exhibits excited state intramolecular proton transfer (ESIPT). The quenching of the T1 tautomeric form by 3O2 had been detected in transient absorption experiments, and was explained in terms of physical quenching (T1–3O2 energy transfer) and chemical reaction This result is in accord with the spin correlation rules, as the reactions of the two triplet species are spin-allowed, the singlet–triplet reactions are spinforbidden.
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