2014
DOI: 10.1002/chem.201402270
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A New 3,5‐Bisporphyrinylpyridine Derivative as a Fluorescent Ratiometric Probe for Zinc Ions

Abstract: A new 3,5-disubstituted pyridine with two porphyrin moieties was prepared through an efficient synthetic approach involving 2-formyl-5,10,15,20-tetraphenylporphyrin (1), piperidine, and catalytic amounts of [La(OTf)3]. 3,5-Bis(5,10,15,20-tetraphenylporphyrin-2-ylmethyl)pyridine (2) was fully characterized and its sensing ability towards Zn(2+), Cu(2+), Hg(2+), Cd(2+), and Ag(+) was evaluated in solution by absorption and fluorescence spectroscopy and in gas phase by using matrix-assisted laser desorption/ioniz… Show more

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Cited by 38 publications
(14 citation statements)
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“…Probes 130 – 134 are benzoporphyrins, and probes 135 – 139 are porphyrin‐2‐ylpyridines (see Figure ) . Probe 141 is a 3,5‐disubstituted pyridine with two porphyrin moieties (Figure ) . Porphyrin‐based probes 143 a – e contain an α,β‐unsaturated ketone unit in a β‐pyrrolic position, and probes 145 a – d are pyrazole–porphyrin conjugates (see Figure ) …”
Section: Red Fluorescent Dyesmentioning
confidence: 99%
“…Probes 130 – 134 are benzoporphyrins, and probes 135 – 139 are porphyrin‐2‐ylpyridines (see Figure ) . Probe 141 is a 3,5‐disubstituted pyridine with two porphyrin moieties (Figure ) . Porphyrin‐based probes 143 a – e contain an α,β‐unsaturated ketone unit in a β‐pyrrolic position, and probes 145 a – d are pyrazole–porphyrin conjugates (see Figure ) …”
Section: Red Fluorescent Dyesmentioning
confidence: 99%
“…In relation to the changesi nthe excited state, aq uenching of the emission intensity in the two bands centered at 648 and 714 nm due to free-base porphyrin emission Q(0-0)a nd Q(0-0)(0-1) [27] is accompanied by an increase of an ew band at 600 nm. This band can be attributed to am etal-to-ligand charget ransfer [24] and reveals the formation of an ew fluorophore from the metal-porphyrin association.…”
Section: Metal Binding Studiesmentioning
confidence: 90%
“…Some of those porphyrin derivatives revealed selectivity to specific metal ions. [21][22][23][24] Herein, we presentt he synthesis of several multiporphyrin derivatives (covalently linked) and the study of their interaction with metal ions. The aim of this study was to find how the number of porphyrin units and the geometry of the multiporphyrin systems can affect the coordination of metal ions.…”
Section: Introductionmentioning
confidence: 99%
“…In this context, porphyrins, well-known by their highly intense colors and key roles in basic mechanisms of living organisms are considered a special class of heterocyclic ligands, due to their unique properties, namely a high ability to coordinate a wide range of metal ions affording stable complexes [32,33,34,35,36,37,38]. In fact, the porphyrin capacity to recognize specific analytes has attracted the attention of the scientific community in the chemical sensing field, due to a possible selectivity enhancement involving supramolecular chemistry concepts [34,39].…”
Section: Introductionmentioning
confidence: 99%