Abstract
Time-resolved spectroscopies and DFT calculations were utilized to investigate the photoredox mechanisms of naphthoquinone compounds. 5-Methoxy-8-tetrahydropyrane-1,4-naphthoquinone (NQ) and 2-methyl-3-(3-methylbut-2-en-1-yl) 1,4-naphthoquinone (MNQ) were excited to singlet excited species (labeled NQ(S1) and MNQ(S1), respectively). NQ(S1) underwent intersystem crossing to produce a triplet NQ, which further underwent hydrogen atom transfer to form a biradical intermediate. The biradical underwent electron transfer to form a zwitterion, followed by cyclization and proton transfer to generate a photoproduct. MNQ(S1) underwent a 1,4-proton transfer process to produce a quinone methide intermediate (1,3-QM) with zwitterionic character, which tautomerized to 1,2-QM. Then, 1,2-QM underwent electrocyclization. The substituent on the parent naphthoquinone is the key factor leading to the different reaction processes for NQ and MNQ.
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