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Photochemistry of naphthosultine and naphthosulfolene in acetonitrile solutions

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The photochemistry of naphthosulfolene (1) and naphthosultine (2) was investigated using time-resolved laser flash photolysis, conventional photochemical steady-state techniques and product analysis. Excited by a laser pulse at 266 nm using laser-induced transient absorption spectroscopy, both compounds 1 and 2 exhibit the typical excited triplet state peaks with maxima at 410 nm and 430 nm in acetonitrile solution under deoxygenated conditions. Interestingly, upon direct photolysis in acetonitrile solution, compound 2 has three additional peaks located at 380 nm, 500 nm and 525 nm, generated by two distinct mechanisms: (1) the cleavage of the C—O bond in the sultine molecule produces a singlet biradical with absorption bands located at 500 nm and 525 nm, which decays at a much lower rate than does the excited triplet state which absorbs at 410 nm and 430 nm; (2) a simultaneous cleavage of the C—O bond and C—S bond in the sultine molecule generates a triplet biradical with absorption band located at 380 nm. Steady-state product studies indicate that reaction (1) is much more favorable than reaction (2), and the decay of the singlet biradical generates naphthosulfolene 1 in high yields in the absence or presence of quenching agents (electron-poor alkenes). The reactivity of the excited triplet states, the singlet biradical and the triplet biradical are discussed.


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