Synthesis and evaluation of aryl oxalates as peroxyoxalate chemiluminescence reagents

ANALYSTANALYST Pub Date: DOI: 10.1039/AN9891401413

Abstract

Eight aryl oxalates having an alkyoxy moiety were synthesised to improve the solubility in acetonitrile for the peroxyoxalate chemiluminescence reaction system. Of these, bis[2-(3,6-dioxaheptyloxycarbonyl)-4-fluorophenyl] oxalate showed the highest solubility (1685 mM). To evaluate these esters together with some known aryl oxalates as chemiluminescence reagents, a simple and rapid method using a flow injection system was developed. The chemiluminescence reaction system consisted of an oxalate, hydrogen peroxide, triethylamine and 9,10-diphenylanthracene in acetonitrile. Of the oxalates synthesised, bis[2-(3,6-dioxaheptyloxycarbonyl)-4-bromophenyl] oxalate gave the highest intensity, which was about 100 times lower than that of bis(2,4-dinitrophenyl) oxalate. However, the chemiluminescence intensities of the oxalates synthesised continued for a far longer period of time than those of commercially available oxalates.

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