Synthesis and characterisation of an intermediate in the peroxyoxalate chemiluminescence: 4-chlorophenyl O,O-hydrogen monoperoxyoxalate

Abstract

The peroxyoxalate system undergoes one of the most efficient chemiluminescence reactions and is the only one supposed to involve an intermolecular chemically induced electron exchange luminescence mechanism, with proven high efficiency. Several reactive intermediates are proposed in the literature, which, upon interaction with an activator dye, lead to excited state generation. In this work, we report the synthesis, spectral characterisation and chemiluminescence properties of 4-chlorophenyl O,O- hydrogen monoperoxyoxalate (1), a compound analogous to one of the proposed reactive intermediates. In the presence of the activator dye 9,10-diphenylanthracene (DPA) alone, 1 does not exhibit any chemiluminescence emission. This fact eliminates compounds of this type as possible reactive intermediates in the peroxyoxalate reaction. However, the addition of various bases [i.e. imidazole, potassium tert-butoxide, potassium p-chlorophenolate and 1,8-bis(dimethylamino)naphthalene] to 1 in the presence of DPA results in high intensity light emission.