Systematic Modulation of the Fluorescence Brightness in Boron‐Dipyrromethene (BODIPY)‐Tagged N‐Heterocyclic Carbene (NHC)–Gold–Thiolates |
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| Authors: | Prof?Dr Israel Fernández Prof?Dr Herbert Plenio |
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| Affiliation: | 1. Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Madrid, Spain;2. Organometallic Chemistry, TU Darmstadt, Darmstadt, Germany |
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| Abstract: | Five different highly fluorescent boron‐dipyrromethene (BODIPY)‐tagged N‐heterocyclic carbene NHC–gold halide complexes were synthesized. The substitution of the halogeno ligand by 4‐substituted aryl thiolates leads to a decrease in the brightness of the complexes. This decrease depends on the electronic nature of the thiols, being most pronounced with highly electron‐rich thiols (4‐R=NMe2). The brightness of the gold thiolates also depends on the distance between the sulfur atom and the BODIPY moiety. The systematic variation of the electron density of (NHC–bodipy)Au(SC6H4R)] (via different R groups) enables the systematic variation of the fluorescence brightness of an appended BODIPY fluorophore. Based on this and supported by DFT calculations, a photoinduced electron‐transfer quenching appears to be the dominant mechanism controlling the brightness of the appended BODIPY dye. |
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| Keywords: | BODIPY gold fluorescence ligand substitution photoinduced electron transfer |
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