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Issue 2, 2014
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Chemiluminescent 2,6-diphenylimidazo[1,2-a]pyrazin-3(7H)-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(7H)-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.

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

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Publication details

The article was received on 28 Jun 2013, accepted on 13 Aug 2013 and first published on 14 Aug 2013


Article type: Paper
DOI: 10.1039/C3PP50197C
Citation: Photochem. Photobiol. Sci., 2014,13, 182-189
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    Chemiluminescent 2,6-diphenylimidazo[1,2-a]pyrazin-3(7H)-ones: a new entry to Cypridina luciferin analogues

    Y. Ishii, C. Hayashi, Y. Suzuki and T. Hirano, Photochem. Photobiol. Sci., 2014, 13, 182
    DOI: 10.1039/C3PP50197C

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