Fluorescent Probes from Aromatic Polycyclic Nitrile Oxides: Isoxazoles versus Dihydro-1λ 3 ,3,2λ 4 -Oxazaborinines

Anthracenenitrile oxide undergoes 1,3-dipolar cycloaddition reaction with propargyl bromide affording the expected isoxazole as single regioisomer, suitably synthetically elaborated and functionalized with a protected triple bond. The introduction of a bromine atom at the position C10 of the anthrac...

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Bibliographic Details
Published inChemistryOpen (Weinheim) Vol. 8; no. 6; pp. 770 - 780
Main Authors Moiola, Mattia, Bova, Antonio, Crespi, Stefano, Memeo, Misal G, Mella, Mariella, Overkleeft, Herman S, Florea, Bogdan I, Quadrelli, Paolo
Format Journal Article
LanguageEnglish
Published Germany John Wiley & Sons, Inc 01.06.2019
Subjects
Anthracene
Boron
Bromine
Chemistry
Cycloaddition
Fluorescent indicators
Imaging techniques
Optical properties
Solvents
enamino-ketones
isoxazoles
photophysical studies
boron complexes
fluorescent probes
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Summary:Anthracenenitrile oxide undergoes 1,3-dipolar cycloaddition reaction with propargyl bromide affording the expected isoxazole as single regioisomer, suitably synthetically elaborated and functionalized with a protected triple bond. The introduction of a bromine atom at the position C10 of the anthracene moiety allows for inserting a variety of aromatic and heterocyclic substituents through Suzuki coupling. A two-way synthetic route can lead to simple isoxazole derivatives or, after N-O bond reductive cleavage and BF complexation, enamino ketone boron complexes. The photophysical properties of both the substituted isoxazoles and the corresponding boron complexes were investigated to show the potentialities for the employment as fluorescent tags in imaging techniques. The quite good quantum yield values confirm the suitability of these compounds in the cellular environment. Scope and limitations of the methodology are discussed.
ISSN:2191-1363
2191-1363
DOI:10.1002/open.201900137