A New Pyrrole-2-carboxaldehyde Functionalized Chitosan-Cu(II) Complex-based Chemosensor for Iodide Anion in Aqueous Media
Samuel Adeolu Olugbemi *
Department of Chemistry, College of Physical Sciences, Federal University of Agriculture Abeokuta, Ogun, Nigeria and Department of Science Laboratory Technology, School of Science and Technology, The Gateway Polytechnic, Saapade, Ogun State, Nigeria.
Lateefah Olanike Adebayo
Department of Chemistry, College of Physical Sciences, Federal University of Agriculture Abeokuta, Ogun, Nigeria.
Sheriff Adewuyi
Department of Chemistry, College of Physical Sciences, Federal University of Agriculture Abeokuta, Ogun, Nigeria.
*Author to whom correspondence should be addressed.
Abstract
Iodine is an essential ingredient in thyroid hormones of which both low and high intakes may cause thyroid disease. This study develops a Pyrrole-2-Carboxaldehyde functionalized chitosan-Cu(II) Complex [PCAFC-Cu(II)] chemosensor, for quick and easy detection of iodide ions from its aqueous solutions. PCAFC-Cu(II) complex was synthesized from a simple condensation reaction of chitosan (CS) and pyrrole-2-carboxaldehyde (PCA) along with an aqueous solution of copper(II) salt. The starting materials and the products were characterized by spectroscopic (FT-IR and UV-Visible), X-ray powder diffraction, and microscopic methods (Scanning Electron Microscopy). The PCAFC-Cu(II) colorimetric sensing of I- revealed a color change adduced to the formation of a hydrogen bond or deprotonation of the complex matrix. Colorimetric detection for I- ions was obtained with a detection limit (LoD) of 0.005 M and the complex has high specificity for I- ions detection from a solution consisting of several anions. The synthesized complex [PCAFC-Cu(II)] could serve as an on-site reagent for the qualitative detection of iodide ions.
Keywords: Chemosensor, colorimetric detection, complex, anions, condensation, deprotonation
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Duan TW, Yan B, Weng H. Europium activated yttrium hybrid microporous system for luminescent sensing toxic anion of Cr(VI) species. Microporous Mesoporous Mater. 2015;217:196-202. DOI: 10.1016/j.micromeso.2015.06.016
Serpell CJ, Beer PD. Anion Sensors. In comprehensive supramolecular chemistry II. Molecular Sciences and Chemical Engineering. 2017;2017:351-385. DOI: 10.1016/B978-0-12-409547-2.12627-7
Akcil A, Erust C, Gahan CS, Ozgun M, Sahin M, Tuncuk A. Precious metal recovery from waste printed circuit boards using cyanide and non-cyanide lixiviants – a review. Waste Management. 2015;45: 258–271. DOI: 10.1016/j.wasman.2015.01.017
Dar TA, Sankar M. Fused nickel (II) porphyrins-sensing of toxic anions and selected metal ions through supramolecular interactions. Frontiers in Chemistry. 2020;8:595177. DOI: 10.3389/fchem.2020.595177
Bhattacharya R, Flora SJS. Cyanide toxicity and its treatment, in handbook of toxicology of chemical warfare agents. Science Direct. 2009:255-270.
Berhanu AL, No G, Mohiuddin I, Malik AK, Aulakh JS, Kumar V, Kim K. A review of the applications of schiff bases as optical chemical sensors. Trends in Analytical Chemistry. 2019;116:74-91.
Wang Q, Xie Y, Ding Y, Lia X, Zhu W. Colorimetric fluoride sensors based on deprotonation of pyrrole–hemiquinone compounds. Chemical Communications. 2010;46:3669-3671.
Jin R, Sun W, Tang S. A DFT study of pyrrole-isoxazole derivatives as chemosensors for fluoride anion. International Journal of Molecular Sciences. 2012;13(9):10986-10999.
DOI: 10.3390/ijms130910986
d’Ischia M, Napolitano A, Pezzella A. Five-membered Rings with One Heteroatom together with their Benzo and other Carbocyclic-fused Derivatives In Comprehensive Heterocyclic Chemistry III. 2008;3:353-388.
Kaur R, Rani V, Abbot V, Kapoor Y, Konar D, Kumar K. Recent synthetic and medicinal perspectives of pyrroles: An overview. Journal of Pharmaceutical Chemistry- Chemical Science. 2017;1(1): 17-32.
Shantini D, Nainggolan I, Nasution TI, Derman MN, Mustaffa R, Abd Wahab NZ. Hexanal gas detection using chitosan biopolymer as sensing material at room temperature. Journal of Sensors. 2016;2016:1-7.
Article ID 8539169.
Available:http://dx.doi.org/10.1155/2016/8539169
Mutreja R, Thakur A, Goyal A. Chitin and Chitosan: Current status and future opportunities. handbook of chitin and chitosan. In: Volume 1: Preparation and properties. 2020:401-417.
Available:https://doi.org/10.1016/B978-0-12-817970-3.00013-4
Al-Hamdani AA, Hamoodah RG. Transition metal complexes with tridentate ligand: Preparation, spectroscopic characterization, thermal analysis, and structural studies. Baghdad Science Journal. 2016;13(4):770-780.
Kumar SP, Suresh R, Giribabu K, Manigandan R, Munusamy S, Muthamizh S. Synthesis, characterization on nickel schiff base complex and its electrocatalytic sensing nature for Hg2+. International Journal of Innovative Research in Science, Engineering, and Technology. 2015;4(1): 123-130.
Oiye EM, Ribeiro MF, M.ORCID Icon, Katayama JMT, Tadini MC, Balbino MA. et al. 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. 2019;49(6):488-509.
Li B, Liu Z, Li L, Xing Y, Liu Y, Yang X. et al. A schiff base sensor for relay monitoring of In3+ and Fe3+ through “off–on–off” fluorescent signals. New Journal of Chemistry. 2021;45:6753-6759.
Borah N, De S, Gogoia A, Das G. A series of benzothiazole-based schiff bases for the colorimetric sensing of fluoride and acetate ions: Acetate-induced turn-on fluorescence for selectivity. New Journal of Chemistry. 2020;44:18703-18713.
Velmathi S, Reena V, Suganya S, Anandan S. Pyrrole based schiff bases as colorimetric and fluorescent chemosensors for fluoride and hydroxide anions. Journal of Fluorescence. 2012;22:155–162.
Arh-Hwang C, Sheng-Chang L, Chia-Yuan C, Chia-Yun C. Comparative adsorption of Cu(II), Zn(II), and Pb(II) ions in aqueous solution on the crosslinked chitosan with epichlorohydrin. Journal of Hazardous Materials. 2008;154:184-191.
Olugbemi SA, Amoniyan OA. Salami AA. Assessment of the adsorption potential of synthesized chitosan-pyrrole-2-carboxaldehyde schiff base for Cr2+ and Pb2+ Ions from dumpsite Leachate. European Journal of Advanced Chemistry Research. 2023;4(3):30-39.
DOI: 10.24018/ejchem.2023.4.3.132
Anan NA, Hassan SM, Saad EM, Butler IS, Mostafa SI. Preparation, characterization, and pH-metric measurements of 4-hydrosalicylidenechitosan schiff-base complexes of Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Ru(III), Rh(III), Pd(II), and Au(III). Carbohydrate Research. 2011;346:775-793.
Jiao TF, Zhou J, Zhou JX, Gao L, Xing Y, Li X. Synthesis and characterization of chitosan–based schiff base compounds with aromatic substituent groups. Iranian Polymer Journal. 2011;20(2):123-136.
Parthiban C, Ciattini S, Chelazzi L, Elango KP. Colorimetric sensing of anions by Cu(II), Co(II), Ni (II), and Zn(II) complexes of naphthoquinone-imidazole hybrid-Influence of complex formation on selectivity and sensing medium. Sensors and Actuators B. 2016;231:768-778.
Adewuyi S, Bisiriyu IO, Akinremi CA, Amolegbe SA. Synthesis, spectroscopic, surface and catalytic reactivity of chitosan supported Co(II) and Its zerovalentcobalt nanobiocomposite. Journal of Inorganic and Organometallic Polymers and Materials. 2017;27(1):114–121.
Canpolat E, Kaya M. Studies on mononuclear chelates derived from substituted schiff base ligands (part 4): Synthesis and characterization of a new 5-hydroxysalicyliden-paminoacetophenoneoxime and its complexes with Co(II), Ni (II), Cu(II) and Zn(II). Turkish Journal of Chemistry. 2005;29:409.
Zoubi WA, Al-Hamdani AA, Ahmed SD, Ko YG. A new azo‐Schiff base: Synthesis, characterization, biological activity and theoretical studies of its complexes. Wiley Applied Organometallic Chemistry. 2018;32:1-15.
Bakare SB. Cu(II), Co(II), Ni(II), Mn(II), and Zn(II) Schiff base complexes of 3-hydroxy-4-[N-(2-hydroxynaphthylidene)-amino]-naphthalene-1-sulfonic acid: Synthesis, Spectroscopic, thermal, and antimicrobial studies. Polish Journal of Chemical Technology. 2019;21(3):26-34.
Temel H, Cakır U, Ugras HI. Synthesis and characterization of a novel oxovanadium (IV) complex and conductometric studies with N, N’-bis (Salicylidene)-1,2-bis-(p-amino phenoxy) ethane. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. 2004;34(4):819-831.
Capan A, Urus S, Sonmez M. Ru(III), Cr(III), Fe(III) complexes of Schiff base ligands bearing phenoxy Groups: Application as catalysts in the synthesis of vitamin K3. Journal of Saudi Chemical Society. 2018;22:757-766.
Silverstein RM, Webster XF. Spectrometric identification of organic compounds. 7th ed. John Wiley and Son, Inc. USA; 2005.
Shaker SA, Mohammed HA, Al-Hamdani AAS. Preparation, physicochemical, and spectroscopic investigation of thiacetazone and quinalizarin complexes with Mn (II), Fe(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), and Pb(II). Australian Journal of Basic and Applied Sciences. 2010;4(10):5178-5183.
Yousif E, Mehdi BI, Rahimi Y, Salimon J, Salih N, Abdullah BM. Synthesis, structure, and antibacterial activity of some triorganotin (IV) complexes with a benzamido alanime ligand. Journal of Taibah University for Science. 2014;8:276-281.
Kumar S, Nigam N, Gosh T, Duta PK, Yadav RS, Pandey AC. Preparation, characterization, and optical properties of a chitosan-anthraldehyde cross-linkable film. Journal of Applied Polymer Science. 2010;115:3056 –3062.
Vivek N, Gopalan N, Das S, Sasikumar K, Sindhu R, Nampoothiri KM. et al. Synthesis and characterization of transparent biodegradable chitosan: Exopolysaccharide composite films plasticized by bio-derived 1,3-propanediol. Sustainable Chemistry. 2021;2:49–62.
Available:https://doi.org/10.3390/suschem2010004
Annaduzzaman M. Chitosan biopolymer as an adsorbent for drinking water treatment. Investigation on arsenic and uranium. 2015; TRITA-LWR LIC-2015:02 ISSN:1650-8629 ISRN KTH/LWR/LIC ISBN 978-91-7595-593-3.
Cinarli A, Gürbüz D, Tavman A, Birteksöz AS. Synthesis, spectral characterizations and antimicrobial activity of some schiff bases of 4-chloro-2-aminophenol. Bulletin of the Chemical Society of Ethiopia. 2011;25(3):407-417.
Kaushal R, Kumar N, Chaudhary S, Arora S, Awasthi A. Synthesis, spectral characterization, and antiproliferative studies of mixed ligand titanium complexes of adamantylamine. Bioinorganic Chemistry and Applications. 2014;2014:1-12.
Available:http://dx.doi.org/10.1155/2014/142828
Dey SC, Al-Amin M, Rashid TU, Sultan MZ, Ashaduzzaman M, Sarker M, et al. Preparation, characterization, and performance evaluation of chitosan as an adsorbent for remazol red. International Journal of Latest Research in Engineering and Technology. 2016;2(2): 52-62.
Karunakaran K, Thamilarasu P. Removal of Fe(III) from aqueous solutions using ricinus communis seed shell and polypyrrole coated ricinus communis seed shell activated carbons. International Journal of ChemTech Research. 2010;2(1):26.