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Title: | A New 3,5-Bisporphyrinylpyridine Derivative as a Fluorescent Ratiometric Probe for Zinc Ions |
Author: | Moura, Nuno M. M. Nunez, Cristina Santos, Sergio M. Faustino, M. Amparo F. Cavaleiro, Jose A. S. Almeida Paz, Filipe A. Neves, M. Graca P. M. S. Capelo, Jose Luis Lodeiro, Carlos |
Keywords: | BETA-CONDENSATION REACTIONS SUPPORTED DEVICES HIGH SELECTIVITY FORCE-FIELD MERCURY CHEMOSENSORS RECOGNITION SENSOR LUMINESCENCE POLYAMINES |
Issue Date: | 2014 |
Publisher: | WILEY-V C H VERLAG GMBH |
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 Zn2+, Cu2+, Hg2+, Cd2+, 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 Zn2+, Cd2+, Hg2+, and Cu2+. A three-metal-per-ligand molar ratio was obtained in all cases and a significant ratiometric behavior was observed in the presence of Zn2+ with the appearance of a new band at 608nm, which can be assigned to a metal-to-ligand charge transfer. The system was able to quantify 79ppb of Zn2+ 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 Hg2+ and Zn2+ 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. |
Peer review: | yes |
URI: | http://hdl.handle.net/10773/20195 |
DOI: | 10.1002/chem.201402270 |
ISSN: | 0947-6539 |
Publisher Version: | 10.1002/chem.201402270 |
Appears in Collections: | CICECO - Artigos |
Files in This Item:
File | Description | Size | Format | |
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A New 35-Bisporphyrinylpyridine Derivative as a Fluorescent Ratiometric Probe for Zinc Ions_10.1002chem.201402270.pdf | 1.69 MB | Adobe PDF |
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