128649-37-6Relevant academic research and scientific papers
2-ethylphenyl acridine-9-carboxylate and 2,5-dimethylphenyl acridine-9-carboxylate
Sikorski, Artur,Krzyminski, Karol,Konitz, Antoni,Blazejowski, Jerzy
, p. o50-o52 (2005)
The title compounds, 2-ethylphenyl acridine-9-carboxylate, C 22H17NO2, (I), and 2,5-dimethylphenyl acridine-9-carboxylate, C22H17NO2, (II), form triclinic and monoclinic crystals, respectiv
1H and 13C NMR spectra, structure and physicochemical features of phenyl acridine-9-carboxylates and 10-methyl-9-(phenoxycarbonyl) acridinium trifluoromethanesulphonates - alkyl substituted in the phenyl fragment
Krzymiński,Malecha,Zadykowicz,Wróblewska,B?aejowski
experimental part, p. 401 - 409 (2011/03/21)
The 1H and 13C NMR spectra of twelve phenyl acridine-9-carboxylates - alkyl-substituted in the phenyl fragment - and their 10-methyl-9-(phenoxycarbonyl)acridinium salts dissolved in CD3CN, CD3OD, CDCl3/sub
Chemiluminogenic features of 10-Methyl-9-(phenoxycarbonyl)acridinium Trifluoromethanesulfonates alkyl substituted at the benzene ring in aqueous media
Krzyminski, Karol,Ozog, Agnieszka,Malecha, Piotr,Roshal, Alexander D.,Wroblewska, Agnieszka,Zadykowicz, Beata,Blazejowski, Jerzy
, p. 1072 - 1085 (2011/04/16)
10-Methyl-9-(phenoxycarbonyl)acridinium trifluoromethanesulfonates bearing alkyl substituents at the benzene ring were synthesized, purified, and identified. In the reaction with OOH- in basic aqueous media, the cations of the compounds investigated were converted to electronically excited 10-methyl-9-acridinone, whose relaxation was accompanied by chemiluminescence (CL). The kinetic constants of CL decay, relative efficiencies of light emission, chemiluminescence quantum yields, and resistance toward alkaline hydrolysis were determined experimentally under various conditions. The mechanism of CL generation is considered on the basis of thermodynamic and kinetic parameters of the reaction steps predicted at the DFT level of theory. The chemiluminescence efficiency is the result of competition of the electrophilic center at C(9) between nucleophilic substitution by OOH - or OH- and the ability of the intermediates thus formed to decompose to electronically excited 10-methyl-9-acridinone. Identification of stable and intermediate reaction products corroborated the suggested reaction scheme. The results obtained, particularly the dependency of the "usefulness" parameter, which takes into account the CL quantum yield and the susceptibility to hydrolysis, on the cavity volume of the entity removed during oxidation, form a convenient framework within which to rationally design chemiluminescent 10-methyl-9-(phenoxycarbonyl)acridinium cations.
Acridinium compounds as chemiluminogenic label
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, (2008/06/13)
New acridinium compounds are provided which comply with formula 1, wherein A is a divalent organic moiety, such as an alkylene chain, X is a group which can be transformed together with C-9 of the acridine into a dioxetane by reaction with hydrogen peroxide, such as an aryloxy group, Y is a counter ion, and Z is a functional group, such as a carboxyl derivative. These acridinium compounds are useful as chemiluminogenic labels for both heterogeneous and homogeneous immunoassays.
