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Issue 2, 2008

The reaction mechanism for the high quantum yield of Cypridina (Vargula) bioluminescence supported by the chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridinaluciferin analogues)

Author affiliations

Abstract

To establish the reaction mechanism of the high-quantum-yield bioluminescence in Cypridina (Vargula), we investigated the chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones (1H) as Cypridina luciferin analogues in DMSO1,1,3,3-tetramethylguanidine and in diglymeacetate buffer. We found that the chemiluminescence of 1H with an electron-donating aryl group, such as a 4-(dimethylamino)phenyl, 3-indolyl or 3-(1-methyl)indolyl group, gave a high quantum yield (ΦCL) in diglymeacetate buffer. This indicates that the reaction mechanism producing this high ΦCL involves the chemiexcitation of a neutral dioxetanone intermediate possessing an electron-donating aryl group to the singlet excited state of neutral acetamidopyrazine (the light emitter). In addition, we investigated the fluorescence of acetamidopyrazines and performed DFT calculations for neutral dioxetanones and the transition states (TS) of the dioxetanone's decomposition. The results made it clear that the electron-donating aryl group gives the TS and the singlet-excited acetamidopyrazine (S1) a strong intramolecular charge transfer (ICT) character, and their similar ICT character leads to the ICT TS → S1 route in the charge transfer-induced luminescence (CTIL) mechanism for efficient chemiexcitation. The reaction mechanism of the chemiluminescence of 1H can explain the highly efficient chemiexcitation of Cypridina bioluminescence.

Graphical abstract: The reaction mechanism for the high quantum yield of Cypridina (Vargula) bioluminescence supported by the chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues)

Article information


Submitted
03 Sep 2007
Accepted
21 Nov 2007
First published
12 Dec 2007

Photochem. Photobiol. Sci., 2008,7, 197-207
Article type
Paper

The reaction mechanism for the high quantum yield of Cypridina (Vargula) bioluminescence supported by the chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues)

T. Hirano, Y. Takahashi, H. Kondo, S. Maki, S. Kojima, H. Ikeda and H. Niwa, Photochem. Photobiol. Sci., 2008, 7, 197 DOI: 10.1039/B713374J

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