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• W2061712524 abstract "Coelenterate luciferin analog having bulky tert-butyl group at the 2-position was suitable for studies on chemiluminescence under various conditions. Photooxygenation of the analog(s) at low temperature (−78°C) afforded luminous intermediates which were proved as peroxides by reduction with PPh3 with resultant loss of luminescence ability. In order to clarify these structures of accumulated luminous intermediates by means of 13C NMR, three 13C enriched analogs were synthesized at the 2, 3 and 5 positions of 3,7-dihydroimidazo[1,2-a]pyrazin-3-one skeleton in 99% enrichment with site-specificity. These 13C-enriched coelenterate luciferin analogs were photooxygenated at −78°C to form two peroxidic products as luminescent intermediates. Structures of these unstable intermediates were deduced by means of 13C NMR spectra at low temperatures using substrates enriched at three sites by 13C. Photooxygenation in a mixture of CF3CD2OD and CD3OD as highly protic solvents afforded the dioxetanone and 2-hydroperoxide. These two peroxides emitted light independently at different temperatures either at 400 nm (neutral species) and/or 475 nm (anionic species) after diluting to 10−5 M in diglyme (DGM) containing acid or base." @default.
• W2061712524 created "2016-06-24" @default.
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• W2061712524 date "1996-09-01" @default.
• W2061712524 modified "2023-09-23" @default.
• W2061712524 title "Low-temperature photooxygenation of coelenterate luciferin analog synthesis and proof of 1,2-dioxetanone as luminescence intermediate" @default.
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• W2061712524 doi "https://doi.org/10.1016/0040-4020(96)00699-0" @default.
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