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Synthesis of 2-aminoBODIPYs by palladium catalysed amination

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Abstract

Palladium catalysed coupling of the 2-iodoBODIPY 3 with a range of anilines and a primary alkylamine succeeds in generating the corresponding 2-aminoBODIPYs. These 2-aminoBODIPY derivatives are non-emissive and quantum chemical calculations and electrochemistry are consistent with charge transfer from the amine substituent. Attenuation of this charge transfer pathway by conversion of the 1,2-phenylenediamine derivative 9 into the corresponding benzimidazolone 10 restores the fluorescence and has been used as the basis for a fluorescence sensor for phosgene.

Graphical abstract: Synthesis of 2-aminoBODIPYs by palladium catalysed amination

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Publication details

The article was received on 18 Jul 2017, accepted on 17 Aug 2017 and first published on 31 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01767G
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis of 2-aminoBODIPYs by palladium catalysed amination

    R. B. Alnoman, P. Stachelek, J. G. Knight, A. Harriman and P. G. Waddell, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01767G

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