A BODIPY/pyridine conjugate for reversible fluorescence detection of gold(iii) ions

Abstract

We designed a "turn-on" type fluorescent probe based a BODIPY-Pyridine conjugate which exhibits high selectivity towards Au(III) ions and, also responds to changes in the pH within the acidic pH range. The probe offers features such as rapid response time, a low detection limit, high sensitivity and selectivity. The detection of Au(III) is recognized by a distinct change in the emission intensity which relies on a reversible "ligand to ion" binding mechanism. We have also documented the utility of the probe for the quantification of gold ion residues in synthetic end products prepared via gold catalysis

A fluorescein-based chemodosimeter for selective gold(III) ion monitoring in aqueous media and living systems

“…Fluorescein hydrazide 1 and alkynyl benzaldehyde derivatives were refluxed in ethanol to give the title compounds, FL-1 and FL-2, in a yield of approximately 60%. The structures of both probes were also unambiguously confirmed by 1 H-NMR, 13 C NMR, and mass spectroscopy, as detailed in the Supporting Information (SI).…”

“…FL-2 issued a highly similar fluorometric response to Au 3+ ions under the same sensing conditions. Moreover, treating FL-2 with Au 3+ selectively afforded FL-2P as the single product, as confirmed by 1 H NMR, 13 C NMR, and high-resolution mass spectroscopy analysis (S10 and S12, SI). The structure of the isolated product revealed that the receptor unit had undergone a highly selective endo-dig intramolecular cyclisation process to yield a sixmembered ring isoquinoline derivative.…”

“…In fact, several different types of fluorescent gold ion probes have appeared in literature on the topic, most of them bearing a receptor unit specifically for gold ions, one which translates the binding event into a detectable optical signal [9][10][11][12][13][14][15][16][17][18][19]. Several receptor units, mostly alkynes and some hydrazone derivatives, were shown to have an exceptional affinity for gold ions, and among these units, the alkyne moiety is a particularly excellent receptor candidate for gold ions.…”

A theoretical and experimental NMR study of BODIPY 493/503: difluoro{2‐[1‐(3,5‐dimethyl‐2H‐pyrrol‐2‐ylidene‐N)ethyl]‐3,5‐dimethyl‐1H‐pyrrolato‐N}boron

“…Compound 1 is bright, green fluorescent dye with similar excitation and emission to fluorescein with several uses in biochemistry, for staining lipids, membranes and other lipophilic compounds, because they exhibit narrow emission bandwidths, they have high extinction coefficient and fluorescence quantum yields and they are photostable. [1] Other applications of these dyes are related to fluorescent probes, [2][3][4] deep-red lighting sources, [5] bioactive CO-releasing molecules [6] and solar cells, [7] amongst many others. [8][9][10] Concerning BODIPY NMR properties, there are several compounds with reported data (Scheme 1) especially related to [11] ; 4, 1 J 11B19F = 33.4 Hz [12] ; 5, 11 B = 0.28, 1 J 11B19F = 28.7 Hz [13] ; 6, 11 B = 0.…”

“…Compound 1 is bright, green fluorescent dye with similar excitation and emission to fluorescein with several uses in biochemistry, for staining lipids, membranes and other lipophilic compounds, because they exhibit narrow emission bandwidths, they have high extinction coefficient and fluorescence quantum yields and they are photostable . Other applications of these dyes are related to fluorescent probes, deep‐red lighting sources, bioactive CO‐releasing molecules and solar cells, amongst many others …”