85474-33-5Relevant academic research and scientific papers
Experimental evidence of the occurrence of intramolecular electron transfer in catalyzed 1,2-dioxetane decomposition
Ciscato, Luiz Francisco M. L.,Bartoloni, Fernando H.,Weiss, Dieter,Beckert, Rainer,Baader, Wilhelm J.
supporting information; experimental part, p. 6574 - 6580 (2010/11/17)
The activation parameters for the thermal decomposition of 13 acridinium-substituted 1,2-dioxetanes, bearing an aromatic moiety, were determined and their chemiluminescence emission quantum yields estimated, utilizing in situ photosensitized 1,2-dioxetane generation and observation of its thermal decomposition kinetics, without isolation of these highly unstable cyclic peroxides. Decomposition rate constants show linear free-energy correlation for electron-withdrawing substituents, with a Hammett reaction constant of Φ = 1.3 ± 0.1, indicating the occurrence of an intramolecular electron transfer from the acridinium moiety to the 1,2-dioxetane ring, as postulated by the intramolecular chemically initiated electron exchange luminescence (CIEEL) mechanism. Emission quantum yield behavior can also be rationalized on the basis of the intramolecular CIEEL mechanism, additionally evidencing its occurrence in this transformation. Both relations constitute the first experimental evidence for the occurrence of the postulated intramolecular electron transfer in the catalyzed and induced decomposition of properly substituted 1,2-dioxetanes.
Toward a chemiluminescent molecular device: Metal ion-enhanced chemiluminescence of benzylidenacridan with 15-monoazacrown-5
Motoyoshiya, Jiro,Tanaka, Toshimitsu,Kuroe, Motoki,Nishii, Yoshinori
experimental part, p. 1014 - 1018 (2009/08/08)
The benzylidenacridans (1a-d) with one or more methoxy groups emit light from the excited N-methylacridone (NMA) when treated with a solution of sodium hypochlorite and alkaline hydrogen peroxide, in which a Hammett relationship with a negative ρ value wa
Substituent Effect on the Chemiluminescence Quantum Efficiency of Some Acridan Derivatives
Perkizas, George,Nikokavouras, John
, p. 3 - 11 (2007/10/02)
Eight 9-benzylidene-N-methylacridan derivatives were synthesized and their chemiluminescence quantum yields on recation with NAOCl-H2O2 or O3 in N,N-dimethylformamide were plotted versus Hammett's "?" values.A good linear fit was obtained, the higher quantum yields being associated with negative "?" values.Two acridans did not fit in the plot and a novel treatment of chemiluminescence quenching is outlined to account for the discrepancy. - Keywords: Acridans; Chemiluminescence; Hammett; Quenching
