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

Several 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.

Automated summary

Several new acridinium esters 2-9 with different substituents on their central acridinium ring have been synthesized and tested for their chemiluminescent properties. The esters with 2,5-dimethylphenyl emit light slowly, while the esters with 2,6-dinitrophenyl and 2,6-bis(trifluoromethyl)phenyl emit light rapidly. The hydrolytic stabilities of the compounds are influenced by the substituent at the 10 position.