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Singlet oxygen (O2) has been widely used in organic synthesis to introduce oxygen-containing functional groups. It is usually generated from ground state oxygen via photochemical triplet sensitization using various organic dyes. To clarify the factors for increasing the efficiency of the reaction, we report a systematic determination of the rate constants observed for the generation of O2 from commonly used triplet sensitizers, i.e., methylene blue, rose bengal, eosin Y, tetraphenylporphyrin, and C60, using the ene reaction of 2,3-dimethyl-2-butene as a probe reaction utilizing 395 and 525 nm LEDs. A faster reaction was accomplished by the larger quantum yield for the generation of O2, longer irradiation wavelength (), higher intensity of incident light (E), and larger  (the product of the irradiation wavelength  and molar extinction coefficient at ).

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Rate constant for the generation of 1O2 from commonly used triplet sensitizers: a systematic study of the wavelength effect using the ene reaction of 2,3-dimethyl-2-butene