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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Capelo, José Luis Núñez, Cristina Neves, M. Graça P. M. S. Almeida Paz, Filipe A. Santos, Sérgio M. Moura, Nuno M. M. Faustino, M. Amparo F. Cavaleiro, José A. S. Lodeiro, Carlos |
| Description | Author Affiliation: Moura NM ( Department of Chemistry and QOPNA, University of Aveiro, Campus de Santiago, 3810-193 Aveiro (Portugal)) |
| 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/ionization (MALDI)-TOF mass spectrometry. Strong changes in the ground and excited state were detected in the case of the soft metal ions $Zn^{2+},$ $Cd^{2+},$ $Hg^{2+},$ and $Cu^{2+}.$ A three-metal-per-ligand molar ratio was obtained in all cases and a significant ratiometric behavior was observed in the presence of $Zn^{2+}$ with the appearance of a new band at 608 nm, which can be assigned to a metal-to-ligand charge transfer. The system was able to quantify 79 ppb of $Zn^{2+}$ and the theoretical calculations are in accordance with the stoichiometry observed in solution. The gas-phase sensorial ability of compound 2 towards all metal ions was confirmed by using MALDI-TOF MS and in solid state by using polymeric films of polymethylmethacrylate (PMMA) doped with ligand 2. The results showed that compound 2 can be analytically used to develop new colorimetric molecular devices that are able to discriminate between $Hg^{2+}$ and $Zn^{2+}$ in solid phase. The crystal structure of $Zn^{II}$ complex of 3,5-bisporphyrinylpyridine was unequivocally elucidated by using single-crystal X-ray diffraction studies. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 22 |
| Volume Number | 20 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2014-05-26 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Porphyrins Chemistry Spectrometry, Fluorescence Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Zinc Crystallography, X-Ray Fluorescent Dyes Chemical Synthesis Gases Ions Molecular Conformation Piperidines Polymethyl Methacrylate Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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