Triazolyl alkoxy fischer carbene complexes in conjugation with ferrocene/pyrene as sensory units: multifunctional chemosensors for lead(II), copper(II), and zinc(II) ions

Ponniah S., Joseph ; Barik, Subrat Kumar ; Thakur, Arunabha ; Ganesamoorthi, R. ; Ghosh, Sundargopal (2014) Triazolyl alkoxy fischer carbene complexes in conjugation with ferrocene/pyrene as sensory units: multifunctional chemosensors for lead(II), copper(II), and zinc(II) ions Organometallics, 33 (12). pp. 3096-3107. ISSN 0276-7333

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Official URL: http://pubs.acs.org/doi/abs/10.1021/om5003396

Related URL: http://dx.doi.org/10.1021/om5003396

Abstract

The regioselective 1,3-dipolar cycloaddition reaction of alkoxy alkynyl Fischer carbene complex 1 with azidomethyl ferrocene 2 and with azidomethyl pyrene 4 under solvent-free conditions yielded the triazolyl Fischer carbene complexes 3 (C27H21O6N3FeW) and 5(C33H21O6N3W), respectively. The cation complexation properties of these receptors have been systematically studied using electrochemical and spectroscopic techniques. The exceptional structural feature existing in these receptors is the presence of a Fischer carbene moiety, connected to the ferrocene or pyrene moiety through a 1,2,3-triazole ring. Receptor 3 contains a redox-active ferrocene moiety and is highly selective toward Pb2+ ion, whereas receptor 5, having a fluorescent pyrene unit, selectively recognizes Zn2+ and Cu2+ ions. The binding ability of receptor 3 can be inferred either from the redox shift (the anodic shift ΔE1/2 = 55 mV) or the highly visual output response for Pb2+ ion. Receptor 5 displays considerable chelation-enhanced fluorescence (CHEF) upon binding with Zn2+ and Cu2+ ions in an aqueous environment. Further, the proposed binding modes of these receptors and their metal cation complexation properties have been supported by 1H NMR titration and MALDI-MS and a DFT study.

Item Type:Article
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ID Code:109024
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