Journal
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
Volume 330, Issue -, Pages 15-21Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jphotochem.2016.07.015
Keywords
Pyrene; Amide; Imide; Fluorescence; Electronic structure; TD DFT calculations
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Directed lithiation of pyrene-1-carboxamides, followed by reaction with DMF, afforded 7-hydroxy-8,9-dihydro-7H-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. (C) 2016 Elsevier B.V. All rights reserved.
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