Acridine Derivatives

Chemiluminogenic Properties of 10-Methyl-9-(phenoxycarbonyl)acridinium Cations in Organic Environments

“…The chromatograms of all the reaction mixtures also revealed the presence of signals attributed to the ester fragment of AE (the leaving groups, LG). We calculated the amounts of these substances, assuming that in an acidic environment they represent the various phenols that may dissociate from the substrate upon oxidation. ,, However, the results are not fully conclusive, as in most cases we obtained values much lower than the expected 100 mol % (we obtained values close to 100% only for 3 and 6 in AN/DBU). One cannot exclude the possibility that the signals occur accidentally in the range characteristic of phenols, but they were in fact due to different substances, e.g., phenyl carbonates.…”

“…According to the all of reported mechanisms of AE CL, light emission is due to the relaxation of excited molecules of 10-methyl-9-acridinones, which are the main final products of AE oxidation. ,, Hence, the emission spectra recorded during CL (stationary CL spectra) should correspond to the fluorescence spectra of the respective derivative of 9-acridinone present in the postreaction mixture and, if it is the only emitter, to the fluorescent spectra of the latter.…”

“…Typically, the oxidation of AE in an aqueous environment is initiated by the action of a peroxide anion (OOH − ) generated in situ in basic hydrogen peroxide solution; the process is accompanied by the relatively effective emission of light (chemiluminescence), reaching quantum yields of ca. 2% and lying within the blue range of spectrum. − We investigated the mechanism of this rather complicated process in detail with respect to the simplest AE (10-methyl-9-(phenoxycarbonyl)acridinium cation) using modern quantum chemistry methods, including the DFT level of theory . The results revealed the multistep nature of the oxidation of AE and of the intermediates that may be produced along the reaction pathway.…”

Chemiluminogenic Features of 10-Methyl-9-(phenoxycarbonyl)acridinium Trifluoromethanesulfonates Alkyl Substituted at the Benzene Ring in Aqueous Media

“…Acridinium derivatives are readily oxidized with hydrogen peroxide, persulfates, and other oxidants in alkaline media leading to chemiluminescence (CL). The light-emitting species are electronically excited 9-acridinones formed as a result of the decomposition of the addition products of OOH − to acridinium cations. ,, This feature of acridinium salts has prompted their use as chemiluminescent indicators or chemiluminogenic fragments of labels in medical, biochemical, , chemical, and environmental analyses.…”

“…The light-emitting species are electronically excited 9-acridinones formed as a result of the decomposition of the addition products of OOH − to acridinium cations. ,, This feature of acridinium salts has prompted their use as chemiluminescent indicators or chemiluminogenic fragments of labels in medical, biochemical, , chemical, and environmental analyses. They have been employed in quantitative immunoassays of antigens, antibodies, or hormones with detection limits at the subattomole levels (detection limits as low as 10 −17 M have been reported). , They can also be used to determine concentrations of highly reactive entities occurring in living matter, such as OOH − . , They have been successfully applied in flow-injection techniques, cellular studies, and nucleic acid diagnostics, as well as in electrochemiluminogenic assays of substances. , Acridinium salts exhibit a higher chemiluminescence quantum yield in aqueous media relative to luminol derivatives and, unlike the latter systems, do not require a catalyst to cause the emission of light. , For these reasons, numerous commercially available chemiluminescent labels contain a 9-(phenoxycarbonyl)acridinium fragment substituted at the benzene moiety. ,, A disadvantage of the use of these compounds, however, is their tendency to form nonchemiluminescing “pseudobases” in aqueous basic or neutral media. ,, In order to minimize this effect, derivatives substituted at the benzene ring have been investigated under a wide range of analytical conditions . There are also other acridinium derivatives substituted at C(9) with carboxamide, cyanide, and hydroxamic acid or other groups, whose chemiluminogenic features have been investigated in the context of possible analytical applications.…”