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3124296 
Journal Article 
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 
2016 
Yes 
Dyes and Pigments
ISSN: 0143-7208
EISSN: 1873-3743 
Elsevier Ltd 
125 
331-338 
English 
WOS:000367777100041 
The lithiation of N-tert-butylpyrene-1-carboxamide with nBuLi-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-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 (λmax = 425-451 nm; ΦF = 15.1-40.8%) and in the solid state ((λmax = 410-555 nm; ΦF = 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. © 2015 Elsevier Ltd. 
Pyrene; Amide; Directed lithiation; Fluorescence; X-ray structure; pi-stacking