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Issue 28, 2015
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Diphenylether based derivatives as Fe(III) chemosensors: spectrofluorimetry, electrochemical and theoretical studies

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Abstract

4-(2,4-Dinitrophenoxy)-3-methoxybenzaldehyde (DPE-I) and (4-(2,4-dinitrophenoxy)-3-methoxyphenyl)methanol (DPE-II) were synthesized with high yield and characterized by spectroscopic techniques. The complexation behaviours of DPE-I and DPE-II for various cationic species (Na+, K+, Mg2+, Cu2+, Ba2+, Cr3+, Fe3+, Co2+, Ni2+, Zn2+, Cd2+, and Pb2+) in HEPES buffered CH3CN : H2O system were investigated and compared by spectroscopic and voltammetric techniques. Both receptors showed high degree of selectivity for Fe3+ over other cations. Receptors showed 1 : 1 complexation with Fe3+. DPE-I showed fluorescence quenching on complexation with Fe3+ ion at 350 nm due to PET (photon induced transfer) mechanism between Fe3+ and the large π electron conjugate system of ligand, while DPE-II displayed emission band at 314 nm which underwent fluorescence quenching selectively on gradual addition of Fe3+ at 314 nm and simultaneously a new band at 424 nm emerged with isosbestic point at 355 nm which increases with increase in Fe3+ conc. Electrochemically, DPE-I due to presence of electron withdrawing (aldehydic group) facilitates reduction of nitro group on benzene ring of the molecule so, peak potentials of the two curves obtained for DPE-I appear at −1.16 V (Epc1) and −1.39 V (Epc2) respectively, while in DPE-II (methanolic group) due to its electron donating character makes the reduction of nitro group a little difficult due to which peak potentials occur at higher potential as compared to DPE-I i.e. at −1.30 V (Epc1) and −1.43 V (Epc2) respectively.

Graphical abstract: Diphenylether based derivatives as Fe(iii) chemosensors: spectrofluorimetry, electrochemical and theoretical studies

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Publication details

The article was received on 16 Jan 2015, accepted on 18 Feb 2015 and first published on 18 Feb 2015


Article type: Paper
DOI: 10.1039/C5RA00969C
Author version available: Download Author version (PDF)
Citation: RSC Adv., 2015,5, 21831-21842
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    Diphenylether based derivatives as Fe(III) chemosensors: spectrofluorimetry, electrochemical and theoretical studies

    R. Sharma, M. Chhibber and S. K. Mittal, RSC Adv., 2015, 5, 21831
    DOI: 10.1039/C5RA00969C

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