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Chemiluminescent 2,6-diphenylimidazo[1,2- a]pyrazin-3(7 H)-ones: a new entry to Cypridina luciferin analogues

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Abstract

An investigation of the chemiluminescent properties of 2,6-diphenylimidazo[1,2- a]pyrazin-3(7 H)-one derivatives (1), having substituted phenyl groups, is described. Among the derivatives 1, the 6-[4-(dimethylamino)phenyl] derivatives (1a,d–f) gave a high quantum yield (ΦCL ≥ 0.0025) in diglyme/acetate buffer, which is a model reaction condition for the Cypridina bioluminescence. Their efficient chemiluminescence is mainly caused by the electronic effect of the substituent at C6. In particular, the electron-donating 4-(dimethylamino)phenyl group at C6 of 1a,d–f plays an essential role in increasing the chemiexcitation efficiency (ΦS) by the charge transfer-induced luminescence (CTIL) mechanism. The results provide useful information for designing new Cypridina luciferin analogues showing efficient chemiluminescence.

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Authors and Affiliations

  1. Department of Engineering Science, Graduate School of Informatics and Engineering, The University of Electro-Communications, Chofu, Tokyo, 182-8585, Japan

    Yuki Ishii, Chihiro Hayashi, Yoshihisa Suzuki & Takashi Hirano

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  1. Yuki Ishii
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  2. Chihiro Hayashi
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  3. Yoshihisa Suzuki
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  4. Takashi Hirano
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Correspondence to Takashi Hirano.

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In memory of the late Professor Nicholas J. Turro.

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Ishii, Y., Hayashi, C., Suzuki, Y. et al. Chemiluminescent 2,6-diphenylimidazo[1,2- a]pyrazin-3(7 H)-ones: a new entry to Cypridina luciferin analogues. Photochem Photobiol Sci 13, 182–189 (2014). https://doi.org/10.1039/c3pp50197c

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