Abstract
Abstract Directed lithiation of pyrene-1-carboxamides, followed by reaction with DMF, afforded 7-hydroxy-8,9-dihydro-7 H -phenaleno-[1,9- ef ]isoindoles, which were oxidized with Jones reagent to the corresponding pyrene-1,2-dicarboximides. Similarly, the reaction of lithiated N - tert -butylpyrene-1-carboxamide with tert -butyl isocyanate afforded N,N’ -di- tert -butylpyrene-1,2-dicarboxamide. The electronic structure and photophysical properties of these compounds were studied by means of theoretical (TD DFT) calculations and experimental (steady-state and time-resolved fluorescence) methods and were compared with those of their pyrene-1- monocarbonyl counterparts. The obtained results reveal the considerable influence of the carbonyl group at the 2-position on the structure and luminescent properties of this class of pyrenyl fluorophores.
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