Chemiluminescence of Electrochemically Oxidized 9-(Phenylthiophosphoryloxymethylidene)-10-methylacridan Derivatives

✍ Scribed by Fakhradin Mirkhalaf; Robert Wilson

• Book ID: 102183670
• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 334 KB
• Volume: 17
• Category: Article
• ISSN: 1040-0397
• DOI: 10.1002/elan.200403280

✦ Synopsis

Abstract

The electrochemistry and electrochemiluminescence (ECL) properties of acridan phosphate ester are reported. Electrochemical oxidation of 9‐(phenylthiophosphoryloxymethylidene)‐10‐methylacridan disodium salt (Compound 1) yields the corresponding acridinium ester. The latter undergoes a fast reaction with hydrogen peroxide forming an intermediate, which produces electronically excited 9‐methyl acridone and emits blue light after relaxation to the ground state. The electrochemical oxidation of this compound appears to occur in two one‐electron steps and light emission is observed for both steps. The chemiluminescence reaction could also be triggered by electrochemical oxidation of Compound 1 in the absence of H~2~O~2~ when the solution was saturated with O~2~. Mechanisms for these reactions based on ECL, voltammetry and in situ UV‐vis identification of the oxidation products are proposed. Due to the low electrode potential required to achieve ECL emission and the occurrence of light emission in the absence of hydrogen peroxide, this compound is proposed as a label for rapid and sensitive determination of biomolecules in automated analysis.