Luminol chemiluminescence: Chemistry, excitation, emitter

✍ Scribed by Merényi, Gábor ;Lind, Johan ;Eriksen, Trygve E.

• Book ID: 101716117
• Publisher: John Wiley and Sons
• Year: 1990
• Weight: 279 KB
• Volume: 5
• Category: Article
• ISSN: 0884-3996
• DOI: 10.1002/bio.1170050111

✦ Synopsis

The mechanism of luminol chemiluminescence is a special case of nucleophilic addition t o carbonyl compounds. The breakdown of the key intermediate, an alpha hydroxy hydroperoxide, produces a peracid ortho t o an acyl diazene group. After intramolecular addition of the peracid, the energy from nitrogen expulsion is utilized in the formation of an anti-aromatic endoperoxide. Rupture along the 0.0 bond leaves a substantial part of the ensuing phthalate in its excited state. The emitter is shown t o be a mono-protonated phthalate unaccessible by photoexcitation. The dark reaction is a concerted decomposion of the alpha hydroxy hydroperodixe t o yield ground-state phthalate.