DEVELOPMENT OF THE CHEMISTRY OF THE IMIDAZOPYRAZIONONE-BIOLUMINESCENCE SYSTEM: FROM THE BIO- AND CHEMILUMINESCENCE MECHANISM TO A DESIGN OF SENSOR MOLECULES

摘要

The imidazo[l,2-a]pyrazin-3(7tf)-one (imidazopyrazinone) ring system is a core structure of the luminescent substrates isolated from marine bioluminescent organisms, such as the jellyfish Aequorea and the crustacean Cypridina (Vargula). To develop the chemistry of the imidazopyrazinone-bioluminescence system, we have systematically investigated the bio- and chemiluminescent properties of imidazopyrazinone derivatives as well as their physical properties. As the results of our studies, we could clarify the unique 7t-electronic character of the imidazopyrazinone rc-system.1 In this paper, we will explain the fundamental chemistry of imidazopyrazinone derivatives and will explore the problem of molecular recognition in bioluminescent processes and the problem of the chemiluminescence reaction. In addition to these studies, we found that the n-electronic character of imidazopyrazinone derivatives was sensitive to interactions with molecular environments, such as a hydrogen-bonding interaction and a Lewis acid/base interaction.1'2 These interactions with molecular environments caused the continuous spectral change of the imidazopyrazinone derivatives. We will also show that imidazopyrazinone derivatives are useful as sensor molecules for determining the hydrogen-bond donor strength of a solvent and the Lewis acidity of a metal ion.