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Directed lithiation of a pyrene-l-carboxamide as a route to new pyrenyl fluorophores

Wrona-Piotrowicz, A; Ciechanska, M; Zakrzewski, J; Metivier, R; Brosseau, A; Makal, A DYES AND PIGMENTS 2016, 125, 331-338.

The lithiation of N-tert-butylpyrene-1-carboxamide with nBuLi-TMEDA in THF at -78 degrees 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-7H-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-7H-phenaleno-[1,9-ef]isoindole-7,9(8H)dione. All of the synthesized compounds displayed fluorescence in solution (lambda(max) = 425-451 nm; Phi(F) = 15.1-40.8%) and in the solid state ((lambda(max) = 410-555 nm; Phi(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 pi-stacked aggregates. The formation of aggregates in the crystals of the latter compounds was confirmed by a single-crystal X-ray diffraction study.

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Paru le 1 février 2016

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DOI: 10.1016/j.dyepig.2015.10.031