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ISSN 2319-7625 (Online) www.chemistry-journal.org

An Overview on Metal Complexes of selected Schiff-bases

with their Electrochemical and Sensor Aspects

Sofani Tafesse Gebreyesus and Masood Akhtar Khan

Department of Chemistry,

College of Natural Sciences, Arbaminch University, ETHIOPIA.

(Received on: December 25, 2014)

ABSTRACT

Schiff bases and their metal complexes are used for many applications apart from the biological activities; it can be used as sensors electrodes, energy storage devices, solar cells and environmental sensor. This review deals more about their use in electrochemical and sensor aspects.

Keywords: Schiff base, metal complex, electrochemical, sensor.

INTRODUCTION

Schiff bases are condensation products of primary amines with carbonyl compounds and they were first reported by Hugo Schiff in 1864. The common structural feature of these compounds is the azomethine group with a general formula RHC=NR’ where R and R’ are alkyl, aryl, cyclo alkyl or heterocyclic groups which may be variously substituted. These compounds are also known as anils, imines or azomethines.1

Schiff bases have wide applications in food industry, dye industry, analytical chemistry, catalysis, fungicidal, agrochemical and biological activities.2

In recent years, the attention of Schiff bases and their metal complexes are increasing due to their remarkable biological and pharmacological applications.3 They are used for many applications apart from the biological activities; it can be used as sensors4, 5 electrodes, energy storage devices, solar cells6 and environmental sensor.7

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20 Sofani Tafesse Gebreyesus, et al., J. Chem. & Cheml. Sci. Vol.5 (1), 19-27 (2015)

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Application of many new analytical devices requires the presence of organic reagents as essential compounds of the measuring system. Schiff base ligands are used in optical and electrochemical sensors, and likewise in several chromatographic methods, to make possible detection of enhance selectivity and sensitivity.10–12

Schiff base ligands can be easily synthesized by reactions of condensation of primary amines and carbonyl compounds in which the azomethine bond is formed and they can used as complex formation reactions (determination of amines, carbonyl compounds and metal ions); or utilizing the variation in their spectroscopic characteristics.

A great number of metal complexes of the Schiff bases (acyclic or cyclic) have been prepared, and they have provided an enormously rich world of chemistry13. This paper reviews the uses of metal complex of Schiff bases in electrochemical and sensor aspects.

1. Electrochemical sensing of N1,N1-bis((E)-2-(2-hydroxy5 bromobenzylideneamino) ethyl)ethane-1,2-diamine to Pyrocatechol

The electrochemical sensing behavior of Schiff base towards pyrocatechol (PC) was examined by cyclic voltammetry (CV). The Schiff base was coated on the GCE surface by the drop coating method. There is an electrocatalytic ability of the modified electrode. This electrocatalytic effect was enhancing due to the larger surface area available on the modifying GCE. The study showed that the reduction peak current moved negatively, but the oxidation peak was not showing any characteristic response. Based on that, reduction peak was accounted for detection of PC.

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In addition the electrode reaction was based on the hydrogen bond formation between the Schiff base and the PC. The catalytic reaction facilitates electron transfer between PC and the Schiff base modified electrode; as a result the electrochemical reduction of PC becomes easier. In the electrocatalytic reaction the diffusion process was carried by the sensing material. The reason is that the Schiff base could increase the rate of electron transfer and lower the over potential of PC at the bare electrode.

Thus, it is clear that Schiff base modified GCE can be successfully used for the electrochemical sensing of PC14,15 .

The Schiff base was used to sensing the pyrocatechol. From the electrochemical sensing experiment, it can be concluded that the Schiff base has good sensing activity towards the pyrocatechol. Hence, the GCE modified with Schiff base will be good sensor for pyrocatechol16.

2. Electrochemical sensing of N1,N1-bis((E)-2-(2-hydroxy5 bromobenzylideneamino) ethyl)ethane-1,2-diamine to Hydroquinone :

Electrocatalytic sensing ability of the polymerized Schiff base (P-SB) modified GCE was investigated by using cyclic voltammetry (CV) and Differential pulse voltammetry (DPV). It is known that the sensing occur irreversible redox process and potential shifted positively. The modified GCE has good conduct with the analyte to form hydrogen bond, hence it gives two fold higher current response when compare with the bare GCE. It is clear that the Schiff base modified GCE is a good electro-catalytic sensor for sense the hydroquinone.17

It is possible also to determine the quantity of hydroquinone in the modified GCE using DPV, which generally has high sensitivity and selectivity. Schiff base was electrochemically polymerized and used for the electro-catalytic sensor. The results demonstrated that Schiff base was successfully used for the detection of hydroquinone. It is more efficient electrode material towards the hydroquinone detection with better electrocatalytic activity and higher sensitivity18.

3. Electrochemical properties of N,N0-bis(2-methoxy phenylidene)-1,5-diamino naphthalene and N,N0-bis(3,4,5-trimethoxy phenylidene)-1,5-diamino naphthalene

Fig.2: Proposed structures of the synthesized Schiffbase compounds Electrochemical properties of the Schiff base compounds (L1 and L2) were studied in NBu4BF4 as supporting electrolyte. The compound L1 shows theirreversible and quasi reversible redox processes at all scan rates.

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22 Sofani Tafesse Gebreyesus, et al., J. Chem. & Cheml. Sci. Vol.5 (1), 19-27 (2015)

January, 2015 | Journal of Chemistry and Chemical Sciences | www.chemistry-journal.org

Fig.2: Proposed structures of the synthesized Schiffbase compounds

In this process, the oxygen atoms of the methoxy groups of the organic compounds give the electrons to the benzenoidrings and then to the nitrogen atoms by the resonance. This process occurs as the reversible. While the compound L1 has onlyone methoxy group (orthoposition on the benzene rings), the othercompound L2 have three methoxy groups (ortho, meta and parapositions on the benzene rings, respectively). Although the methoxy groups decrease the electron density of the benzenoidrings by the inductive effect, the electron density increase by themesomeric effect. Electron donating groups to the benzene rings shift the potentials from the positive to negative regions. These situations were seen in these compounds. The compound L2 shows irreversible and quasi-reversible processes at other scan rates and concentrations. It is investigated that their sensor properties against to the metal ions.

The compound L2 shows higher selectivity toward the softer cation Hg(II), as compared to the harder caions K(I), Na(I), Ba(II), Cd(II), Co(II), Cu(II), Mg(II), Mn(II), Ni(II), Zn(II) and Al(III) on day light. On the examining conditions, the Schiff base compounds indicated higher selectivity against to the Cu(II) ion. In the electrochemical studies, the compounds showed reversible redox processes at the some scan rates20.

4. Electrochemistry of Schiff Base Complexes Derived from Amino Acids

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metal complexes are very much vital, sincethey axial ligation, degree and

complexes21-25.

The cyclic voltammogram of the complex under N2 atmosphere shows a significant electrochemical process, which is found to follow the one

This reversible process includes the

Zn(II) to Zn(I) and the anodic peak which is a Zn(I) to Zn(II). The reactivity

cyclic voltammogram of conditions. The study proves the

solution media. Furthermore, the chemica

solid state. It is also expected that the electron with complex in Zn(II) state while

oxidation state, Zn(III)30.

From the CV study, the electrochemical data of the complex has been calculated the complex involves the one electron reversible mechanism. On the other

reactivity of the complex with the environmental gases like and proved by the CV study of the complex under

metal complexes are very much vital, sincethey can be used to study the chelate ring size, and distribution of unsaturation and substitution pattern in the

Fig. 3: Synthesis of L and [Zn(L) Cl]Cl

The cyclic voltammogram of the complex under N2 atmosphere shows a significant electrochemical process, which is found to follow the one electron reversible

This reversible process includes the cathodic peak which corresponds to the reduction of Zn(II) to Zn(I) and the anodic peak which is a characteristic of the reversible oxidation of Zn(I) to Zn(II). The reactivity of complex with the aerobic gases such

cyclic voltammogram of the complex in solution media can be studied under aerobic study proves the non-reactivity of complex with the aerobic gases in the media. Furthermore, the chemical inertness of the complex would

solid state. It is also expected that the electron with drawing groups could stabilize the complex in Zn(II) state while the electron donating groups may favor the oxidation to next

From the CV study, the electrochemical data of the complex has been calculated the one electron reversible mechanism. On the other

of the complex with the environmental gases like CO2 and O2 has been als

and proved by the CV study of the complex under aerobic conditions.

can be used to study the chelate ring size, bution of unsaturation and substitution pattern in the

The cyclic voltammogram of the complex under N2 atmosphere shows a significant electron reversible mechanism. to the reduction of of the reversible oxidation of as O2 and CO2 in

media can be studied under aerobic reactivity of complex with the aerobic gases in the

l inertness of the complex would be more in its could stabilize the may favor the oxidation to next

From the CV study, the electrochemical data of the complex has been calculated and the one electron reversible mechanism. On the other hand, the

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24 Sofani Tafesse Gebreyesus,

January, 2015 | Journal of Chemistry and Chemical Sciences

5. Electrochemistry behavior Metal (II) Complexes Derived from Naphthofuran carbohydrazide and Diacetylmonoxime Schiff Base

Fig. 4: Suggested structure for [Co(

The redox property of the Cu(II) complex was investigated by cyclic voltammetry. The electrochemical behavior of electron transfer quasi-reversible redox

6. PVC Based Sensor For Anion Recognition Using 1, 12 dibenzoylcyclotetradeca

The solution for PVC membrane was prepared through mixing of the 33% PVC, 66% dibutylphthalate,1%L1(1,12

2,11-diene) mixed and dissolved in THF. The resulting solution was poured into mould and THF was allowed to evaporate off at room temperature over 24 membrane was obtained. The disc

an Ag-AgCI wire immersed in an internal respective anionic metal solution.

Fig. 5: 12- diaaza

Sofani Tafesse Gebreyesus, et al., J. Chem. & Cheml. Sci. Vol.5 (1),

19-Journal of Chemistry and Chemical Sciences | www.chemistry-journal.org

Electrochemistry behavior Metal (II) Complexes Derived from Naphthofuran carbohydrazide and Diacetylmonoxime Schiff Base

Fig. 4: Suggested structure for [Co(C17H15O3N3)Cl2]n

The redox property of the Cu(II) complex was investigated by electrochemical

The electrochemical behavior of Cu(II) complex exhibited the one reversible redox couple26.

Based Sensor For Anion Recognition Using 1, 12- diaaza-5,8-dioxo dibenzoylcyclotetradeca-2,11-diene Schiff Based Macrocyclic Receptor:

The solution for PVC membrane was prepared through mixing of the 33% PVC, dibutylphthalate,1%L1(1,12-diaaza-5,8-dioxo-3[4],9[10]dibenzoylcyclotetradeca diene) mixed and dissolved in THF. The resulting solution was poured into mould and THF was allowed to evaporate off at room temperature over 24

membrane was obtained. The discs were cut and pasted onto a glass-tube, which consisted of AgCI wire immersed in an internal solution of anionic solution by immersion in its

solution.

diaaza-5,8-dioxo-3[4],9[10]-dibenzoylcyclotetradeca-2,11-diene -27 (2015)

journal.org

Electrochemistry behavior Metal (II) Complexes Derived from Naphthofuran-2-

electrochemical method using Cu(II) complex exhibited the one

dioxo-3[4],9[10]- Receptor:

The solution for PVC membrane was prepared through mixing of the 33% PVC, 3[4],9[10]dibenzoylcyclotetradeca- diene) mixed and dissolved in THF. The resulting solution was poured into a glass mould and THF was allowed to evaporate off at room temperature over 24 h. A flexible tube, which consisted of solution of anionic solution by immersion in its

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The conclusion can be drawn that the Schiff based macrocyclic complexes provide a suitable matrix for the fabrication of membrane sensors for anions. These membrane electrodes are selective to specific anions and can be successfully used as indicator electrodes in the direct analysis of synthetic as well as real samples. These electrochemical sensors also have enough lifetimes for estimation of samples27.

Schiff bases have been used as carriers in the preparation of mpotentiometricsensors for determining cations and anions28-37 . Aruthenium(III) Schiff base complex was used in the fabrication of chloride PVC-based membrane sensor38.

The sensor with a composition of 30% PVC, 62% benzyl acetate, 5% ruthenium(III) Schiff base complex and 3% hexadecyltrimethyl ammonium bromide displays near-Nernstian behavior over a wide concentration range. It shows high selectivity toward chloride ions over several organic and inorganic anions and was successfully applied for the determination of chloride in serum samples. It could also be used as an indicator electrode in the potentiometric titration of chloride ions with silver nitrate solution. Recently, there is a report on a potentiometric aluminium sensor based on the use N,N’-bis(salicylidene)-1,2-cyclohexanediamine as a neutral carrier in poly(vinyl chloride) matrix. It was successfully applied for direct determination of aluminium(III) in biological, industrial and environmental samples39.

The electrode could be used in the pH range of 2.0–9.0 and mixtures containing up to 20% (v/v) non-aqueous content. It has been used as an indicator electrode in potentiometric titration of aluminium ion with EDTA. The Schiff base, N,N′,N″ ,N’’’-1,5,8,12-tetraazadodecane-bis(salicylaldiminato), has been used as ionophore for preparing Mn2+ selective sensor40. The sensor was found to be sufficiently selective for Mn2+ over a number of alkali, alkaline and heavy metal ions and could therefore be used for the determination of manganese in various samples by direct potentiometry.

ACKNOWLEDGEMENT

I would like to give thank to the digital library of College of natural sciences, Arbaminch university. Besides, I would like to appreciate Mrs. Nitsuh Wubeshet, for her support for the review.

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Figure

Fig. 1: graphical representation of electro-catalytic reaction.
Fig. 3: Synthesis of L and [Zn(L) Cl]Cl
Fig. 5: 12- diaazadiaaza-5,8-dioxo-3[4],9[10]-dibenzoylcyclotetradeca-2,11-diene

References

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