Synthesis, structure elucidation, and chemiluminescent activity of new 9‐substituted 10‐(ω‐(succinimidyloxycarbonyl)alkyl)acridinium esters

Abstract

AbstractSeveral new acridinium esters 2–9 having their central acridinium ring bearing a 9‐(2,5‐dimethylphenoxycarbonyl), 9‐(2,6‐bis(trifluoromethyl)phenoxycarbonyl) or 9‐(2,6‐dinitrophenoxycarbonyl) group, and a 10‐methyl, 10‐(3‐(succinimidyloxycarbonyl)propyl), 10‐(5‐(succinimidyloxycarbonyl)pentyl), or 10‐(10‐(succinimidyloxycarbonyl)decyl) group, have been synthesized and their chemiluminescent properties have been tested. The 2,5‐dimethylphenyl acridinium esters emit light slowly (glow) when treated with alkaline hydrogen peroxide, while the 2,6‐dinitrophenyl and 2,6‐bis(trifluoromethyl)phenyl esters emit light rapidly (flash). The substituent at the 10 position affects the hydrolytic stabilities of the compounds.