Chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones in DMSO/TMG and in diglyme/acetate buffer: support for the chemiexcitation process to generate the singlet-excited state of neutral oxyluciferin in a high quantum yield in the Cypridina (Vargula) bioluminescence mechanism |
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| Authors: | Yuto Takahashi Shojiro Maki Hiroshi Ikeda Takashi Hirano |
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| Institution: | a Department of Applied Physics and Chemistry, The University of Electro-Communications, Chofu, Tokyo 182-8585, Japan
b Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan |
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| Abstract: | The chemiluminescence of 6-aryl-2-methylimidazo1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues) in DMSO/1,1,3,3-tetramethylguanidine and in diglyme/acetate buffer was investigated. The results indicate that the reaction mechanism that produces a high chemiluminescence quantum yield involves a chemiexcitation process from a neutral dioxetanone intermediate possessing an electron-donating aryl group (σAr <−0.6) to the singlet-excited state of neutral acetamidopyrazine. This result may be applied to the reaction mechanism for Cypridina (Vargula) bioluminescence. |
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| Keywords: | Chemiluminescence Cypridina bioluminescence Imidazopyrazinone Substituent effects Reaction mechanism |
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