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A new chromophore, 2-(4-nitrophenyl)-1H-indole (NPI), was synthesized as a potential photolabile protecting group. Caged benzoic acids featuring the NPI chromophore were synthesized as model compounds. Benzoic acid was released in moderate yields (~ 40-60%) upon photolysis of the caged benzoic acids without any additional chemical reagents. Interestingly, an aldehyde, 1-(5-(1-formyl-1H-indol-2-yl)-2-nitrophenyl)ethyl benzoate, was isolated in ≈ 20% together with benzoic acid (≈ 40%) in photolysis of a caged benzoic acid, 2-(2-(3-(1-(benzoyloxy)ethyl)-4-nitrophenyl)-1H-indol-1-yl)acetic acid. The functional group, CH 2 COOH, at the indole nitrogen was transformed into the aldehyde group, CHO, under photolysis conditions in air. The similar photochemical transformation was observed in the photolysis of 2-(2-(4-nitrophenyl)-1H-indol-1-yl)acetic acid, in which the benzoate group is not attached at the nitrophenyl ring. Products analysis, transient absorption spectroscopy, and computational study suggested that intramolecular electron transfer is key for the elimination of CO 2 and absorption of O 2 for the formation of the aldehyde. The artificial breathing-type reaction can apply to transition metal-free oxidation of amino acids under mild conditions.

Light-triggered elimination of CO2 and absorption of O2 (artificial breathing reaction) in photolysis of 2-(4-nitrophenyl)-1H-indole derivatives