Utilization of a Fluorescent Dye Molecule as a Proton and Electron Reservoir

Angewandte Chemie
Ian A KiefferZachariah M Heiden

Abstract

Fluorescent dyes have been widely utilized as chemical sensors and in photodynamic therapy, but exploitation of their redox-active nature in chemical reactions has remained mostly unexplored. This report describes the isolation of a 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based radical. The redox-active nature of the BODIPY compound can be utilized in combination with a guanidine center, the basicity of which can be manipulated by greater than 14 pKa units, to promote the conversion of protons and electrons into H-atoms for transfer to substrate molecules.

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Citations

May 29, 2018·Chemistry : a European Journal·Chengjie LiBernhard Kräutler
Sep 5, 2019·Chemical Communications : Chem Comm·Brena L ThompsonZachariah M Heiden
Jan 1, 2019·New Journal of Chemistry = Nouveau Journal De Chimie·Tanner B HansonZachariah M Heiden
Apr 29, 2021·Physical Chemistry Chemical Physics : PCCP·Brena L Thompson, Zachariah M Heiden
Jun 3, 2021·Organic & Biomolecular Chemistry·Khurnia Krisna Puji PamungkasToshiaki Murai
Dec 7, 2021·Accounts of Chemical Research·Elisa Tomat, Clayton J Curtis
Jan 5, 2022·Chemical Communications : Chem Comm·Brena L ThompsonZachariah M Heiden

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