158749-58-7Relevant academic research and scientific papers
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
experimental part, 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.
Spectral features of substituted 9-(phenoxycarbonyl)-acridines and their protonated and methylated cation derivatives
Krzyminski, Karol,Roshal, Alexander D.,Niziolek, Agnieszka
, p. 394 - 402 (2008/09/21)
The long-wavelength absorption of eight 9-(phenoxycarbonyl)-acridines and the 10-H-9-(phenoxycarbonyl)-acridinium and 10-methyl-9-(phenoxycarbonyl)-acridinium cations derived from them, substituted with an alkyl or trifluoroalkyl group at the benzene ring
Acridinium compounds and conjugates thereof
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, (2008/06/13)
Acridinium compounds represented by the general formula (I) where A is an intervening group which does not have activity for binding with a specific binding substance, Z is a labelling active group which has activity for binding with a specific binding substance, R1 is a halogen atom, an alkyl group or an aryl group; R2, R3, R4 and R5 are each a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a nitro group, a halogen atom or a carbonyl group, and Y is a counter ion. The acridinium compounds may form conjugates with specific binding substances. The acridinium compounds have high emission efficiency and stability and, hence, are useful as chemiluminescence labelling agents.
