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Competitive one-pot reactions: Simultaneous synthesis of decahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes and photophysical characterization
Martinez Gomez, Sugey M.,Alzate Sanchez, Diego M.,Rodriguez-Cordoba, William,Sierra, Cesar A.,Ochoa-Puentes, Cristian
, p. 648 - 659 (2014)
A simple and convenient one-pot method for simultaneously obtaining decahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthene derivatives is described. A high conversion yielding both products was obtained under the reaction conditions. To understand the optical behavior of the model compounds and their potential use as antenna moieties in bichromophoric systems, the photophysical properties of all samples were studied using ultraviolet-visible absorption and steady-state fluorescence spectroscopy in methanol solutions. For the case of the acridinediones, the fluorescence spectra were found to exhibit the typical emission profile of the locally excited state, whereas, contrary to previous published experimental results, reliable fluorescence emission spectra for the xanthenes derivatives could not be obtained. On the other hand, the poor quantum yields of the synthesized decahydroacridine-1,8-diones were explained based on the benzene-like substitution effect, which favors the intersystem crossing relaxation mechanism. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright
