Directed lithiation of a pyrene-1-carboxamide as a route to new pyrenyl fluorophores
| Autor: | Janusz Zakrzewski, Magdalena Ciechańska, Rémi Métivier, Anna Makal, Arnaud Brosseau, Anna Wrona-Piotrowicz |
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| Rok vydání: | 2016 |
| Předmět: |
Quenching (fluorescence)
010405 organic chemistry Chemistry Stereochemistry medicine.drug_class Process Chemistry and Technology General Chemical Engineering Carboxamide 010402 general chemistry 01 natural sciences Medicinal chemistry Fluorescence 0104 chemical sciences chemistry.chemical_compound Monomer Reagent Amide medicine Pyrene Isoindole |
| Zdroj: | Dyes and Pigments. 125:331-338 |
| ISSN: | 0143-7208 |
| DOI: | 10.1016/j.dyepig.2015.10.031 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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