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Synthesis of 2-aminoBODIPYs by palladium catalysed amination

Lookup NU author(s): Rua Alnoman, Patrycja Stachelek, Dr Julian Knight, Emeritus Professor Anthony Harriman, Dr Paul Waddell

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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.

Publication metadata

Author(s): Alnoman RB, Stachelek P, Knight JG, Harriman A, Waddell PG

Publication type: Article

Publication status: Published

Journal: Organic and Biomolecular Chemistry

Year: 2017

Volume: 15

Issue: 36

Pages: 7643-7653

Print publication date: 28/09/2017

Online publication date: 31/08/2017

Acceptance date: 17/08/2017

Date deposited: 18/08/2017

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: Royal Society of Chemistry

URL: https://doi.org/10.1039/C7OB01767G

DOI: 10.1039/C7OB01767G

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