Preparation, Structural Characterization, Electrochemistry, and Sensing Properties toward Anions and Cations of Ferrocene-Triazole Derivatives

A number of monosubstituted (3, 4, 6, 8, 9, 11, and 13) and disubstituted (15 and 16) ferrocene-derived triazoles have been prepared, by using the copper-catalyzed click reaction, and fully characterized. The versatility of the click reaction enables the decoration of the ferrocene-triazole core, wi...

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Published inOrganometallics Vol. 32; no. 20; pp. 5740 - 5753
Main Authors Romero, Tomás, Orenes, Raúl A, Tárraga, Alberto, Molina, Pedro
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.10.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
AMINO-ACID
CLICK CHEMISTRY
SELECTIVE RECOGNITION
RECEPTOR
REDOX
MULTICHANNEL RECOGNITION
FLUORESCENT SENSORS
CHARGE-TRANSFER
HYDROGEN SULFATE
ELECTRONIC-STRUCTURE
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Summary:A number of monosubstituted (3, 4, 6, 8, 9, 11, and 13) and disubstituted (15 and 16) ferrocene-derived triazoles have been prepared, by using the copper-catalyzed click reaction, and fully characterized. The versatility of the click reaction enables the decoration of the ferrocene-triazole core, with additional substituents displaying different optoelectrochemical properties. The most salient features derived from the sensing studies are that receptors 3, 6, 15, and 16 undergo unprecedented cathodic shifts of the oxidation peak of the ferrocene/ferrocenium redox couple in the presence of F–, AcO–, H2PO4 –, and HP2O7 3– anions, whereas receptors 11 and 16 behave as dual redox and optically selective molecular sensors for Hg2+ cations. The isolated [6 3·Ni2+] complex has been characterized by X-ray analysis.
ISSN:0276-7333
1520-6041
DOI:10.1021/om4002457