Anna Wrona-Piotrowicz, M. Ciechańska, J. Zakrzewski
Feb 1, 2016
Citations
0
Influential Citations
7
Citations
Journal
Dyes and Pigments
Abstract
Abstract The lithiation of N-tert -butylpyrene-1-carboxamide with n BuLi-TMEDA in THF at −78 °C afforded, after quenching with chlorosilanes, the corresponding 2-(trialkylsilyl)pyrene-1-carboxamides. When DMF and diethyl oxalate were used as quenchers compounds having 8- tert -butyl-7-hydroxy-8,9-dihydro-7 H -phenaleno-[1,9- ef ]isoindole skeleton were obtained. The oxidation of compound having secondary OH group with Jones’ reagent afforded 8- tert -butyl-7-hydroxy-8,9-dihydro-7 H -phenaleno-[1,9- ef ]isoindole-7,9(8 H )dione. All of the synthesized compounds displayed fluorescence in solution ( λ max = 425–451 nm; Φ F = 15.1–40.8%) and in the solid state (( λ max = 410–555 nm; Φ F = 6–40%). The silylated amides display in the solid state monomer emission whereas in the case of the of phenalenoisoindole derivatives the emitting species are π-stacked aggregates. The formation of aggregates in the crystals of the latter compounds was confirmed by a single-crystal X-ray diffraction study.