Journal
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
Volume 293, Issue -, Pages 12-25Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jphotochem.2014.07.016
Keywords
Imidazo[1,2-alpha]pyrazin-3(7H)-one; Chemiluminescence; Substituent effect
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Funding
- Japan Society for the Promotion of Science (JSPS) [25410179, 22550031]
- MEXT-Supported Program for the Strategic Research Foundation at Private Universities
- Grants-in-Aid for Scientific Research [22550031, 25410179] Funding Source: KAKEN
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6,8-Diphenylimidazopyrazinone derivatives having a substituent R (R=CF3, H, and OMe) at pare position of the 8-phenyl group were synthesized and their chemiluminescent properties were investigated. The chemiluminescence maxima (CLmax) of these compounds were observed to be in the range of 513-553 nm with a bathochromic shift that increased with the electron-withdrawing character of R, contrary to the previously observed substituent effect at the 6-postion. The chemiluminescence efficiencies (phi(CL)) of these imidazopyrazinones were improved by the introduction of a p-substituted phenyl group at the 8-position. The quantitative investigation of the three quantum efficiencies (phi(R), phi(S), and phi(FL)) whose product gives us phi(CL) revealed that the phi(CL) gains made were largely because of the increase in the values of the fluorescence quantum yields of the corresponding light emitters (phi(FL)). The yields of the singlet-excited emitters (phi(S)) during the chemiluminescent reaction were found to be very small (0.015-0.019), suggesting that one cannot construct an efficient imidazopyrazinone-chemiluminescence system that is comparable to the aequorin bioluminescence system only by using the electronic effects of substituents. (C) 2014 Elsevier B.V. All rights reserved.
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