Chemiluminescence capable compounds have been successfully employed in biomedical and environmental analyses for over 20 years [1]. Derivatives of 10-substituted acridinium-9-carboxylic acid phenyl esters are being used as fragments of tracers used in quantitative immunoassays of biological molecules. A family of 10-methyl-9-(phenoxycarbonyl) acridinium salts, di-substituted at the ortho positions in the lateral phenyl ring with substituents expressing various electronic effects (CH₃, X), were synthesized with good yields. A catalytic esterification of acridine-9-carboxylic acid chloride followed by the alkylation of endocyclic nitrogen using effective methylating agent such as methyl trifluormethanesulfonate was employed [2]. The acridinium esters were analyzed in terms of purity and chemical identity employing, among others, HPLC chromatography and NMR spectroscopy. In order to establish their usefuleness as fragments of chemiluminescence sensors, luminogenic properties of new derivatives were investigated applying absorption and fluorescence spectroscopy supported by theoretical calculations performed at semi-empirical level. Time-resolved measurements were employed to investigate the parameters of chemiluminescence process accompanying the reaction of the acridinium salts with hydrogen peroxide in basic media. Results enabled to obtain pseudo-first order kinetic constants of CL decay, relative CL efficiencies and the stability of the chemiluminogens in aqueous systems having various pH values. Post-reaction products were analyzed in order to establish the proportions between the "light-path" product, that is, 10-methyl-9-acridinone, and the "dark path" (hydrolysis) product, namely, 10-methylacridinium-9-carboxylic acid cation. The perspectives of practical applications of the new compounds are briefly outlined.

(Study supported by state funds for scientific research under BW/8000-5-0280-6).

[1] W. R. G. Baeyens (Ed.) Chemiluminescence in Analytical Chemistry, Garcia-Campana, A. M., Marcel Dekker, Inc., NY, 2001.

[2] A. Wróblewska, K. Krzymiński, J. Rak, J. Błażejowski, O. M. Huta, I. O. Pasaty, R. S. Petryshyn, A. D. Roshal, Book of Abstracts of the XX-th IUPAC Symposium on Photochemistry, Granada, Spain 2004. P355, 598.

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1. Tautomerism of Acridin-9-amines