Electrochemical sensor for determination of butylated hydroxyanisole in real samples using glassy carbon electrode modified by [Co(HL)2Cl2] nano-complex
DOI:
https://doi.org/10.5599/admet.1703Keywords:
Schiff base ligand, cobalt(II) nano-complex, butylated hydroxyanisole, voltammetry
Abstract
A new mononuclear Co(II) complex with the formula [Co(HL)2Cl2] (1) (HL= N-(2-hydroxy-1-naphthylidene)-2-methyl aniline) has been synthesized and characterized by Fourier transform infrared spectroscopy, UV–Vis, elemental analysis and single crystal X-ray structure analysis. Single crystals of the complex [Co(HL)2Cl2] (1) were obtained through slow evaporation of an acetonitrile solution at room temperature. The crystal structure analysis revealed that the two Schiff base ligands create a tetrahedral geometry via oxygen atoms and two chloride atoms. The nano-size of [Co(HL)2Cl2] (2) have been synthesized by the sonochemical process. Characterization of nanoparticles (2) was carried out via X-ray powder diffraction (XRD), scanning electron microscopy (SEM), UV-Vis, and FT-IR spectroscopy. The average sample size synthesized via the sonochemical method was approximately 56 nm. In this work, a simple sensor based on a glassy carbon electrode modified with [Co(HL)2Cl2] nano-complex was developed ([Co(HL)2Cl2] nano-complex/GCE) for convenient and fast electrochemical detection of butylated hydroxyanisole (BHA). The modified electrode offers considerably improved voltammetric sensitivity toward BHA compared to the bare electrode. Applying linear differential pulse voltammetry, a good linear relationship of the oxidation peak current with respect to concentrations of BHA across the range of 0.5–150 µM and a detection limit of 0.12 µM was achieved. The [Co(HL)2Cl2] nano-complex/GCE sensor was applied to the determination of BHA in real samples successfully.
Downloads
References
K.H.G. Freitas, O. Fatibello-Filho. Simultaneous determination of butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) in food samples using a carbon composite electrode modified with Cu3(PO4)2 immobilized in polyester resin. Talanta 81 (2010) 1102-1108. https://doi.org/10.1016/¬j.talanta.¬2010.02.004
D. Thomas, Z. Rasheed, J.S. Jagan, K.G. Kumar. Study of kinetic parameters and development of a voltammetric sensor for the determination of butylated hydroxyanisole (BHA) in oil samples. Journal of Food Science and Technology 52 (2015) 6719-6726. https://doi.org/10.1007/s13197-015-1796-1
S.R. Prabakar, S.S. Narayanan. Surface modification of amine-functionalised graphite for preparation of cobalt hexacyanoferrate (CoHCF)-modified electrode: an amperometric sensor for determination of butylated hydroxyanisole (BHA). Analytical and Bioanalytical Chemistry 386 (2006) 2107-2115. https://doi.org/10.1007/s00216-006-0854-y
M. Cui, S. Liu, W. Lian, J. Li, W. Xu, J. Huang. A molecularly-imprinted electrochemical sensor based on a graphene–Prussian blue composite-modified glassy carbon electrode for the detection of butylated hydroxyanisole in foodstuffs. Analyst 138 (2013) 5949-5955. https://doi.org/10.1039/C3AN01190A
Z. Rasheed, A.E. Vikraman, D. Thomas, J.S. Jagan, K.G. Kumar. Carbon-nanotube-based sensor for the determination of butylated hydroxyanisole in food samples. Food Analytical Methods 8 (2015) 213-221. https://doi.org/10.1007/s12161-014-9894-7
L.F. Capitán‐Vallvey, M.C. Valencia, E.A. Nicolás. Simple resolution of butylated hydroxyanisole and n‐propyl gallate in fatty foods and cosmetics samples by flow‐injection solid‐phase spectrophotometry. Journal of Food Science 68(5) (2003) 1595-1599. https://doi.org/10.1111/¬j.1365-¬2621.¬2003.tb12297.x
N.B. Tombesi, H. Freije, Application of solid-phase microextraction combined with gas chromatography–mass spectrometry to the determination of butylated hydroxytoluene in bottled drinking water. Journal of Chromatography A 963 (2002) 179-183. https://doi.org/10.1016/S0021-9673(02)00217-0
A. Sanches-Silva, J.M. Cruz, R. Sendón-Garcĺa, P. Paseiro-Losada. Determination of butylated hydroxytoluene in food samples by high-performance liquid chromatography with ultraviolet detection and gas chromatography/mass spectrometry. Journal of AOAC International 90 (2007) 277-283. https://doi.org/10.1093/jaoac/90.1.277
Y. Guan, Q. Chu, L. Fu, T. Wu, J. Ye. Determination of phenolic antioxidants by micellar electrokinetic capillary chromatography with electrochemical detection. Food Chemistry 94 (2006) 157-162. https://doi.org/10.1016/j.foodchem.2005.01.015
S. Han, Y. Ding, F. Teng, A. Yao, Q. Leng. Molecularly imprinted electrochemical sensor based on 3D-flower-like MoS2 decorated with silver nanoparticles for highly selective detection of butylated hydroxyanisole. Food Chemistry 387 (2022) 132899. https://doi.org/10.1016/j.foodchem.2022.132899
N.S. Sangeetha, S.S. Narayanan. Effective electrochemical detection of riboflavin and butylated hydroxy anisole based on azure A and nickel hexacyanoferrate framework on graphite electrode. Chemical Data Collections 30 (2020) 100544. https://doi.org/10.1016/j.cdc.2020.100544
H. Karimi-Maleh, R. Darabi, M. Shabani-Nooshabadi, M. Baghayeri, F. Karimi, J. Rouhi, C. Karaman. Determination of D&C Red 33 and Patent Blue V Azo dyes using an impressive electrochemical sensor based on carbon paste electrode modified with ZIF-8/g-C3N4/Co and ionic liquid in mouthwash and toothpaste as real samples. Food and Chemical Toxicology (2022) 112907. https://doi.org/10.1016/¬j.fct.2022.112907
H. Peyman, H. Roshanfekr, A. Babakhanian, H. Jafari. PVC Membrane Electrode Modified by Lawson as Synthetic Derivative Ionophore for Determination of Cadmium in Alloy and Wastewater. Chemical Methodologie 5(5) (2020) 446-453. http://www.chemmethod.com/article_135266.html
H. Beitollahi, S.Z. Mohammadi, M. Safaei, S. Tajik. Applications of electrochemical sensors and biosensors based on modified screen-printed electrodes: a review. Analytical Methods 12 (2020) 1547-1560. https://doi.org/10.1039/C9AY02598G
S. Saghiri, M. Ebrahimi, M.R. Bozorgmehr. NiO nanoparticle/1-hexyl-3-methylimidazolium hexafluoro¬phosphate composite for amplification of epinephrine electrochemical sensor. Asian Journal of Nanosciences and Materials 4 (2021) 46-52. https://doi.org/10.26655/AJNANOMAT.-2021.1.4
Y.F. Mustafa, G. Chehardoli, S. Habibzadeh, Z. Arzehgar. Electrochemical detection of sulfite in food samples. Journal of Electrochemical Science and Engineering 12 (2022) 1061-1079. https://doi.org/-10.5599/jese.1555
T. Eren, N. Atar, M. L. Yola, H. Karimi-Maleh. A sensitive molecularly imprinted polymer based quartz crystal microbalance nanosensor for selective determination of lovastatin in red yeast rice. Food Chemistry 185 (2015) 430-436. https://doi.org/10.1016/j.foodchem.2015.03.153
M.S. Sengar, S. Saxena, S.P. Satsangee, R. Jain. Silver Nanoparticles Decorated Functionalized Multiwalled Carbon Nanotubes Modified Screen Printed Sensor for Voltammetric Determination of Butorphanol. Journal of Applied Organometallic Chemistry 1 (2021) 95-108. https://doi.org/-10.22034/jaoc.2021.289344.1023
M. Mazloum-Ardakani, H. Beitollahi, B. Ganjipour, H. Naeimi. Novel carbon nanotube paste electrode for simultaneous determination of norepinephrine, uric acid and d-penicillamine. International Journal of Electrochemical Science 5 (2010) 531-546.
A. Lohrasbi Nejad. Electrochemical strategies for detection of diazinon. Journal of Electrochemical Science and Engineering 12 (2022) 1041-1059. https://doi.org/10.5599/jese.1379
H. Karimi-Maleh, A.F. Shojaei, K. Tabatabaeian, F. Karimi, S. Shakeri, R. Moradi. Simultaneous determination of 6-mercaptopruine, 6-thioguanine and dasatinib as three important anticancer drugs using nanostructure voltammetric sensor employing Pt/MWCNTs and 1-butyl-3-methylimidazolium hexafluoro phosphate. Biosensors and Bioelectronics 86 (2016) 879-884. https://doi.org/10.1016/¬j.bios.2016.07.086
Z. Mehdizadeh, S. Shahidi, A. Ghorbani-HasanSaraei, M. Limooei, M. Bijad. Monitoring of Amaranth in Drinking Samples using Voltammetric Amplified Electroanalytical Sensor. Chemical Methodologies 6 (2022) 246-252. https://doi.org/10.22034/chemm.2022.324073.1423
S. Tajik, H. Beitollahi, F.G. Nejad, I.S. Shoaie, M.A. Khalilzadeh, M.S. Asl, M. Shokouhimehr. Recent developments in conducting polymers: Applications for electrochemistry. RSC advances 10(62) (2020) 37834-37856. https://doi.org/10.1039/D0RA06160C
A. Shamsi, F. Ahour. Electrochemical Sensing of Thioridazine in Human Serum Samples Using Modified Glassy Carbon Electrode. Advanced Journal of Chemistry-Section A 4 (2021) 22-31. https://doi.org/¬10.22034/¬ajca.2020.252025.1215
P.M. Jahani. Flower-like MoS2 screen-printed electrode based sensor for the sensitive detection of sunset yellow FCF in food samples. Journal of Electrochemical Science and Engineering 12 (2022) 1099-1109. https://doi.org/10.5599/jese.1413
S.A. Alavi-Tabari, M. A. Khalilzadeh, H. Karimi-Maleh. Simultaneous determination of doxorubicin and dasatinib as two breast anticancer drugs uses an amplified sensor with ionic liquid and ZnO nanoparticle. Journal of Electroanalytical Chemistry 811 (2018) 84-88. https://doi.org/10.1016/-j.jelechem.¬2018.01.034
S. Azimi, M. Amiri, H. Imanzadeh, A. Bezaatpour. Fe3O4@SiO2-NH2/CoSB Modified Carbon Paste Electrode for Simultaneous Detection of Acetaminophen and Chlorpheniramine. Advanced Journal of Chemistry-Section A 4 (2021) 152-164. https://doi.org/10.22034/ajca.2021.275901.1246
S. Tajik, M.A. Taher, H. Beitollahi. First report for simultaneous determination of methyldopa and hydrochlorothiazide using a nanostructured based electrochemical sensor. Journal of Electroanalytical Chemistry 704 (2013) 137-144. https://doi.org/10.1016/j.jelechem.2013.07.008
M. Vardini, N. Abbasi, A. Kaviani, M. Ahmadi, E. Karimi. Graphite Electrode Potentiometric Sensor Modified by Surface Imprinted Silica Gel to Measure Valproic Acid. Chemical Methodologies 6 (2022) 398-408. http://www.chemmethod.com/article_147528.html
S. Ariavand, M. Ebrahimi, E. Foladi. Design and Construction of a Novel and an Efficient Potentiometric Sensor for Determination of Sodium Ion in Urban Water Samples. Chemical Methodologies 6(11) (2022) 886-904. https://doi.org/10.22034/chemm.2022.348712.1567
H. Karimi-Maleh, M. Sheikhshoaie, I. Sheikhshoaie, M. Ranjbar, J. Alizadeh, N.W. Maxakato, A. Abbaspourrad. A novel electrochemical epinine sensor using amplified CuO nanoparticles and an-hexyl-3-methylimidazolium hexafluorophosphate electrode. New Journal of Chemistry 43 (2019), 2362-2367. https://doi.org/10.1039/C8NJ05581E
R.M. Mohabis, F. Fazeli, I. Amini, V. Azizkhani. An overview of recent advances in the detection of ascorbic acid by electrochemical techniques. Journal of Electrochemical Science and Engineering 12 (2022) 1081-1098. https://doi.org/10.5599/jese.1561
S. Tajik, M.A. Taher, H. Beitollahi. Simultaneous determination of droxidopa and carbidopa using a carbon nanotubes paste electrode. Sensors and Actuators B: Chemical 188 (2013) 923-930. https://doi.org/10.1016/j.snb.2013.07.085
A. Hosseini Fakhrabad, R. Sanavi Khoshnood, M.R. Abedi, M. Ebrahimi. Fabrication a composite carbon paste electrodes (CPEs) modified with multi-wall carbon nano-tubes (MWCNTs/N, N-Bis (salicyliden)-1,3-propandiamine) for determination of lanthanum (III). Eurasian Chemical Communications 3 (2021) 627-634. https://doi.org/10.22034/ecc.2021.288271.1182
K. Harismah, M. Mirzaei, M. Dai, Z. Roshandel, E. Salarrezaei. In silico investigation of nanocarbon biosensors for diagnosis of COVID-19. Eurasian Chemical Communications 3(2) (2021) 95-102. https://doi.org/10.22034/ecc.2021.267226.1120
H. Karimi-Maleh, C. Karaman, O. Karaman, F. Karimi, Y. Vasseghian, L. Fu, A. Mirabi. Nanochemistry approach for the fabrication of Fe and N co-decorated biomass-derived activated carbon frameworks: a promising oxygen reduction reaction electrocatalyst in neutral media. Journal of Nanostructure in Chemistry (2022) 1-11. https://doi.org/10.1007/s40097-022-00492-3
A. Dehno Khalaji, P. Machek, M. Jarosova, α-Fe2O3 Nanoparticles: Synthesis, Characterization, Magnetic Properties and Photocatalytic Degradation of Methyl Orange. Advanced Journal of Chemistry-Section A 4(4) (2021) 317-326. https://doi.org/10.22034/ajca.2021.292396.1268
R. Hajinasir, M. Esmaeili Jadidi. Synthesis of ZnO nanoparticles via flaxseed aqueous extract. Journal of Applied Organometallic Chemistry 2(2) (2022) 101-108. https://doi.org/10.22034/jaoc.2022.154805
M. Alidadykhoh, H. Pyman, H. Roshanfekr. Application of a New Polymer Agcl Nanoparticles Coated Polyethylene Terephetalat [PET] as Adsorbent for Removal and Electrochemical Determination of Methylene Blue Dye. Chemical Methodologie 5(2) (2021) 96-106. https://doi.org/10.22034/-chemm.2021.119677
N. Koohzadi, Z. Rezayati Zad. A Highly Sensitive Colorimetric Determination of Paraquat by Silver Nanoparticles. Advanced Journal of Chemistry-Section B: Natural Products and Medical Chemistry 3(4) (2021) 311-322. https://doi.org/10.22034/ajcb.2021.302596.1092
M. Miraki, H. Karimi-Maleh, M.A. Taher, S. Cheraghi, F. Karimi, S. Agarwal, V.K. Gupta. Voltammetric amplified platform based on ionic liquid/NiO nanocomposite for determination of benserazide and levodopa. Journal of Molecular Liquids 278 (2019) 672-676. https://doi.org/10.1016/j.molliq.2019.-01.081
H. Beitollahi, I. Sheikhshoaie. Novel nanostructure-based electrochemical sensor for simultaneous determination of dopamine and acetaminophen. Materials Science and Engineering: C 32(2) (2012) 375-380. https://doi.org/10.1016/j.msec.2011.11.009
M. Bijad, A. Hojjati-Najafabadi, H. Asari-Bami, S. Habibzadeh, I. Amini, F. Fazeli. An overview of modified sensors with focus on electrochemical sensing of sulfite in food samples. Eurasian Chemical Communications 3(2) (2021) 116-138. https://doi.org/10.22034/ecc.2021.268819.1122
A. Sahraei, H. Kargar, M. Hakimi, M.N. Tahir. Distorted square-antiprism geometry of new zirconium (IV) Schiff base complexes: Synthesis, spectral characterization, crystal structure and investigation of biological properties. Journal of Molecular Structure 1149 (2017) 576-584. https://doi.org/-10.1016/j.molstruc.2017.08.022
A. Trzesowska-Kruszynska. Copper complex of glycine Schiff base: In situ ligand synthesis, structure, spectral, and thermal properties. Journal of Molecular Structure 1017 (2012) 72-78. https://doi.org/¬10.1016/j.molstruc.2012.03.003
J. Joseph, G.A.B. Rani. Metal based SOD mimetic therapeutic agents: Synthesis, characterization and biochemical studies of metal complexes. Arabian Journal of Chemistry 10 (2017) S1963-S1972. https://doi.org/10.1016/j.arabjc.2013.07.024
X. Liu, J.R. Hamon. Recent developments in penta-, hexa-and heptadentate Schiff base ligands and their metal complexes. Coordination Chemistry Reviews 389 (2019) 94-118. https://doi.org/-10.1016/j.ccr.2019.03.010
S. Kaya, S. Erkan, D. Karakaş. Computational investigation of molecular structures, spectroscopic pro¬perties and antitumor-antibacterial activities of some Schiff bases. Spectrochimica Acta Part A: Mole¬cular and Biomolecular Spectroscopy 244 (2021) 118829. https://doi.org/10.1016/j.saa.-2020.118829
A.M. Abu-Dief, I.M. Mohamed. A review on versatile applications of transition metal complexes incorporating Schiff bases. Beni-suef University Journal of Basic and Applied Sciences 4(2) (2015) 119-133. https://doi.org/10.1016/j.bjbas.2015.05.004
S.A. Dailami, S.A. Onakpa, M.A. Funtua. Fe (III) and Cr (III) Complexes with Phenolic Schiff Base: Synthesis, Physico-Chemical Characterisation, Antimicrobial and Antioxidant Studies. IOSR Journal of Applied Chemistry 9(9) (2016) 18-23.
E. Tozzo, S. Romera, M.P. dos Santos, M. Muraro, H.D.A. Regina, L.M. Liao, E.R. Dockal. Synthesis, spectral studies and X-ray crystal structure of N, N′-(±)-trans-1, 2-cyclohexylenebis (3-ethoxysalicylideneamine) H2 (t-3-EtOsalchxn). Journal of Molecular Structure 876 (2008) 110-120. https://doi.org/10.1016/j.molstruc.2007.05.043
M. Masoudi, M. Behzad, A. Arab, A. Tarahhomi, H.A. Rudbari, G. Bruno. Crystal structures, DFT calculations and Hirshfeld surface analyses of three new cobalt (III) Schiff base complexes derived from meso-1, 2-diphenyl-1, 2-ethylenediamine. Journal of Molecular Structure 1122 (2016) 123-133. https://doi.org/10.1016/j.molstruc.2016.05.092
P.G. Cozzi. Metal–Salen Schiff base complexes in catalysis: practical aspects. Chemical Society Reviews 33 (2004) 410-421. https://doi.org/10.1039/B307853C
O. Fatibello‐Filho, E.R. Dockal, L.H. Marcolino‐Junior, M.F. Teixeira. Electrochemical modified electrodes based on metal‐salen complexes. Analytical letters 40 (2007) 1825-1852. https://doi.org/¬10.1080/00032710701487122
W. Al Zoubi, N. Al Mohanna. Membrane sensors based on Schiff bases as chelating ionophores–A review. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 132 (2014) 854-870. https://doi.org/10.1016/j.saa.2014.04.176
É.N. Oiye, M.F.M. Ribeiro, J.M.T. Katayama, M.C. Tadini, M.A. Balbino, I.C. Eleotério, M.F. de Oliveira. Electrochemical sensors containing Schiff bases and their transition metal complexes to detect analytes of forensic, pharmaceutical and environmental interest. A review. Critical Reviews in Analytical Chemistry 49(6) (2019) 488-509. https://doi.org/10.1080/10408347.2018.1561242
R.H. Taha, Z.A. El-Shafiey, A.A. Salman, E.M. El-Fakharany, M.M. Mansour. Synthesis and character-rization of newly synthesized Schiff base ligand and its metal complexes as potent anticancer. Journal of Molecular Structure 1181 (2019) 536-545. https://doi.org/10.1016/-j.molstruc.2018.12.055
E. Yousif, A. Majeed, K. Al-Sammarrae, N. Salih, J. Salimon, B. Abdullah. Metal complexes of Schiff base: preparation, characterization and antibacterial activity. Arabian Journal of Chemistry 10 (2017) S1639-S1644. https://doi.org/10.1016/j.arabjc.2013.06.006
M. Biabani, H. Saravani, V. Eigner, M. Dusek. A novel coordination polymer of Cd (II) based on 2-mercaptopyrimidine: sonochemical synthesis, characterization, and antibacterial properties. Journal of Molecular Structure 1166 (2018) 470-478. https://doi.org/10.1016/j.molstruc.2018.04.054
H. Sadeghzadeh, A. Morsali. Sonochemical synthesis and characterization of nano-belt lead (II) coordination polymer: new precursor to produce pure phase nano-sized lead (II) oxide. Ultrasonics Sonochemistry 18(1) (2011) 80-84. https://doi.org/10.1016/j.ultsonch.2010.01.011
M. Saif, H.F. El-Shafiy, M.M. Mashaly, M.F. Eid, A.I. Nabeel, R. Fouad. Synthesis, characterization, and antioxidant/cytotoxic activity of new chromone Schiff base nano-complexes of Zn (II), Cu (II), Ni (II) and Co (II). Journal of Molecular Structure 1118 (2016) 75-82. https://doi.org/10.1016/j.molstruc.¬2016.03.060
Published
How to Cite
Issue
Section
License
Articles are published under the terms and conditions of the
Creative Commons Attribution license 4.0 International.
