Abstract
Metal complexes were obtained by the reaction of zinc, cadmium and mercury(II) salts with Schiff base HL (N(salicylidene)benzylamine). HL was synthesized by the condensation reaction of benzylamine and 2-hydroxybenzaldehyde. The fluorescence properties of the Schiff base and its metal complexes were studied in ethanol-water solutions. HL was examined for its utility as a fuorescent chemosensor for the determination of Zn2+, Cd2+ and Hg2+ in aqueous samples. The HL chemosensor was found to be sensitive to Zn2+, Cd2+ and Hg2+ than some metal ions and its complexes emitted strong fluorescence at 452 nm for Zn2+ at 474 nm for Cd2+ and at 491 nm for Hg2+, respectively. It was determined that HL forms complexes with a ratio of 2:1 for Zn2+ and Hg2+ and with a ratio of 1:1 for Cd2+ by Job plots. For the detection of Zn2+, Cd2+ and Hg2+ in aqueous samples, pH, solvent type and ligand concentration were optimized for an analytical method based on HL chemosensor. HL gave a wide range of linearity with Zn2+, Hg2+ and Cd2+, the limit of detection was found to be 2.7 × 10-7 M, 7.5 × 10-7 M and 6.0 × 10-7 M, respectively.
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Nagesh G, Raj KM, Mruthyunjayaswamy B (2015) Synthesis, characterization, thermal study and biological evaluation of Cu (II), Co (II), Ni (II) and Zn (II) complexes of Schiff base ligand containing thiazole moiety. J Mol Struct 1079:423–432
Zayed EM, Mohamed GG, Hindy AM (2015) Transition metal complexes of novel Schiff base. J Therm Anal Calorim 120(1):893–903
Mahmoud WH, Deghadi RG, Mohamed GG (2016) Novel Schiff base ligand and its metal complexes with some transition elements. Synthesis, spectroscopic, thermal analysis, antimicrobial and in vitro anticancer activity. Appl Organomet Chem 30(4):221–230
Wang P, Lee H (1997) Recent applications of high-performance liquid chromatography to the analysis of metal complexes. J Chromatogr A 789(1-2):437–451
Abu-Dief AM, Mohamed IM (2015) A review on versatile applications of transition metal complexes incorporating Schiff bases. Beni-suef Univ J Basic Appl Sci 4(2):119–133
Dai C-H, Mao F-L (2012) Synthesis and crystal structures of two dinuclear Schiff base cadmium (II) complexes. Synthesis React Inorg Metal-Org Nano-Metal Chem 42(4):537–541
Majumder A, Rosair GM, Mallick A, Chattopadhyay N, Mitra S (2006) Synthesis, structures and fluorescence of nickel, zinc and cadmium complexes with the N, N, O-tridentate Schiff base N-2-pyridylmethylidene-2-hydroxy-phenylamine. Polyhedron 25(8):1753–1762
Mohamed GG, Omar M, Ibrahim AA (2009) Biological activity studies on metal complexes of novel tridentate Schiff base ligand. Spectroscopic and thermal characterization. Eur J Med Chem 44(12):4801–4812
Elerman Y, Kabak M, Tahir MN (1996) Bis (N-2-propylsalicylideneamino-N, O) cobalt (II). Acta Crystallogr Sect C: Cryst Struct Commun 52(10):2434–2436
Atakol O, Kenar A, Kabak M (1997) Some complexes of Nickel (II) with Ono Type Schiff Bases and their Monoligand Adducts. Part II Synthesis and Reactivity in Inorganic and Metal-Organic. Chemistry 27(1):29–40
Chakraborty J, Thakurta S, Samanta B, Ray A, Pilet G, Batten SR, Jensen P, Mitra S (2007) Synthesis, characterisation and crystal structures of three trinuclear cadmium (II) complexes with multidentate Schiff base ligands. Polyhedron 26(17):5139–5149
Saghatforoush LA, Aminkhani A, Ershad S, Karimnezhad G, Ghammamy S, Kabiri R (2008) Preparation of Zinc (II) and Cadmium (II) Complexes of the Tetradentate Schiff Base Ligand 2-((E)-(2-(2-(pyridine-2-yl)-ethylthio) ethylimino) methyl)-4-bromophenol (PytBrsalH). Molecules 13(4):804–811
Germain ME, Vargo TR, Khalifah PG, Knapp MJ (2007) Fluorescent detection of nitroaromatics and 2, 3-dimethyl-2, 3-dinitrobutane (DMNB) by a zinc complex:(salophen) Zn. Inorg Chem 46(11):4422–4429
Basak S, Sen S, Marschner C, Baumgartner J, Batten SR, Turner DR, Mitra S (2008) Synthesis, crystal structures and fluorescence properties of two new di-and polynuclear Cd (II) complexes with N2O donor set of a tridentate Schiff base ligand. Polyhedron 27(4):1193–1200
Maxim C, Pasatoiu TD, Kravtsov VC, Shova S, Muryn CA, Winpenny RE, Tuna F, Andruh M (2008) Copper (II) and zinc (II) complexes with Schiff-base ligands derived from salicylaldehyde and 3-methoxysalicylaldehyde: Synthesis, crystal structures, magnetic and luminescence properties. Inorg Chim Acta 361(14-15):3903–3911
Qian S-S, Zhang M, Wang Y-N, Tian F-Y, Liu L, You Z-L, Zhu H-L (2013) Synthesis, crystal structures, and fluorescent properties of zinc and cadmium (II) complexes with tridentate Schiff bases. J Coord Chem 66(6):1006–1015
Gunnlaugsson T, Lee TC, Parkesh R (2004) Highly selective fluorescent chemosensors for cadmium in water. Tetrahedron 60(49):11239–11249
Lo WK, Wong WK, Wong WY, Guo J (2005) Synthesis, Crystal Structures and Photophysical Properties of Novel Tetranuclear Cadmium (II) Schiff-Base Complexes. Eur J Inorg Chem 2005(19):3950–3954
De Silva AP, Gunaratne HN, Gunnlaugsson T, Huxley AJ, McCoy CP, Rademacher JT, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches. Chem Rev 97(5):1515–1566
Wang L, Qin W, Liu W (2010) A sensitive Schiff-base fluorescent indicator for the detection of Zn2+. Inorg Chem Commun 13(10):1122–1125
You Z-L, Wang X-L, Zhang J-C, Wang C, Zhou X-S (2011) Synthesis, crystal structures, and fluorescence properties of two dinuclear cadmium (II) complexes derived from N-isopropyl-N′-(1-pyridin-2-ylethylidene) ethane-1, 2-diamine. Struct Chem 22(6):1297–1302
Zhou Y, Li Z-X, Zang S-Q, Zhu Y-Y, Zhang H-Y, Hou H-W, Mak TC (2012) A novel sensitive turn-on fluorescent Zn2+ chemosensor based on an easy to prepare C 3-symmetric schiff-base derivative in 100% aqueous solution. Org Lett 14(5):1214–1217
Pamuk M, Algi F (2012) Synthesis of a novel on/off fluorescent cadmium (II) probe. Tetrahedron Lett 53(51):7010–7012
Cai Y, Meng X, Wang S, Zhu M, Pan Z, Guo Q (2013) A quinoline based fluorescent probe that can distinguish zinc (II) from cadmium (II) in water. Tetrahedron Lett 54(9):1125–1128
Hosseini M, Ghafarloo A, Ganjali MR, Faridbod F, Norouzi P, Niasari MS (2014) A turn-on fluorescent sensor for Zn2+ based on new Schiff's base derivative in aqueous media. Sensors Actuators B Chem 198:411–415
Roy N, Pramanik HA, Paul PC, Singh ST (2014) A sensitive Schiff-base fluorescent chemosensor for the selective detection of Zn 2+. J Fluoresc 24(4):1099–1106
Ergun E, Ergun Ü, İleri Ö, Küçükmüzevir MF (2018) An investigation of some Schiff base derivatives as chemosensors for Zn (II): The performance characteristics and potential applications. Spectrochim Acta A Mol Biomol Spectrosc 203:273–286
Wang Y, Ma Z-Y, Zhang D-L, Deng J-L, Chen X, Xie C-Z, Qiao X, Li Q-Z, Xu J-Y (2018) Highly selective and sensitive turn-on fluorescent sensor for detection of Al3+ based on quinoline-base Schiff base. Spectrochim Acta A Mol Biomol Spectrosc 195:157–164
De Acha N, Elosúa C, Corres JM, Arregui FJ (2019) Fluorescent sensors for the detection of heavy metal ions in aqueous media. Sensors 19(3):599
Aazam ES, Husseiny AE, Al-Amri H (2012) Synthesis and photoluminescent properties of a Schiff-base ligand and its mononuclear Zn (II), Cd (II), Cu (II), Ni (II) and Pd (II) metal complexes. Arab J Chem 5(1):45–53
Bayraktutan T, Meral K (2016) Merocyanine 540 adsorbed on polyethylenimine-functionalized graphene oxide nanocomposites as a turn-on fluorescent sensor for bovine serum albumin. Phys Chem Chem Phys 18(33):23400–23406
Bayraktutan T, Onganer Y, Meral K (2016) Polyelectrolyte-induced H-aggregation of Merocyanine 540 and its application in metal ions detection as a colorimetric sensor. Sensors Actuators B Chem 226:52–61
Cheng T, Xu Y, Zhang S, Zhu W, Qian X, Duan L (2008) A highly sensitive and selective OFF-ON fluorescent sensor for cadmium in aqueous solution and living cell. J Am Chem Soc 130(48):16160–16161
Roy P, Dhara K, Manassero M, Banerjee P (2009) Synthesis, characterization and selective fluorescent zinc (II) sensing property of three Schiff-base compounds. Inorg Chim Acta 362(8):2927–2932
Xue L, Liu C, Jiang H (2009) Highly sensitive and selective fluorescent sensor for distinguishing cadmium from zinc ions in aqueous media. Org Lett 11(7):1655–1658
Das S, Sarkar BN, Bhar K, Chattopadhyay S, Fun H-K, Mitra P, Ghosh BK (2010) Classical tetradentate chelation and novel bis (bidentate) congregation motifs of a neutral N-donor Schiff base in dinuclear cadmium (II) complexes: Synthesis, structure and luminescence behaviour. Inorg Chem Commun 13(3):353–357
Fang Z-L, Nie Q-X (2010) Zinc (II) and cadmium (II) complexes of Schiff bases derived from amino acids and pyridine-3-carboxaldehyde: synthesis, crystal structures, and fluorescence. J Coord Chem 63(13):2328–2336
Hu Y, Q-q L, Li H, Guo Q-n, Lu Y-g, Z-y L (2010) A novel class of Cd (II), Hg (II) turn-on and Cu (II), Zn (II) turn-off Schiff base fluorescent probes. Dalton T 39(47):11344–11352
Li L, Dang Y-Q, Li H-W, Wang B, Wu Y (2010) Fluorescent chemosensor based on Schiff base for selective detection of zinc (II) in aqueous solution. Tetrahedron Lett 51(4):618–621
Goswami P, Das DK (2012) A new highly sensitive and selective fluorescent cadmium sensor. J Fluoresc 22(1):391–395
Hsieh WH, Wan C-F, Liao D-J, Wu A-T (2012) A turn-on Schiff base fluorescence sensor for zinc ion. Tetrahedron Lett 53(44):5848–5851
Chen C-H, Liao D-J, Wan C-F, Wu A-T (2013) A turn-on and reversible Schiff base fluorescence sensor for Al 3+ ion. Analyst 138(9):2527–2530
Kim KB, Kim H, Song EJ, Kim S, Noh I, Kim C (2013) A cap-type Schiff base acting as a fluorescence sensor for zinc (II) and a colorimetric sensor for iron (II), copper (II), and zinc (II) in aqueous media. Dalton Trans 42(47):16569–16577
Liu X, Zhang N, Zhou J, Chang T, Fang C, Shangguan D (2013) A turn-on fluorescent sensor for zinc and cadmium ions based on perylene tetracarboxylic diimide. Analyst 138(3):901–906
Liu H-M, Venkatesan P, Wu S-P (2014) A sensitive and selective fluorescent sensor for Zinc (II) and its application to living cell imaging. Sensors Actuators B Chem 203:719–725
Singh TS, Paul PC, Pramanik HA (2014) Fluorescent chemosensor based on sensitive Schiff base for selective detection of Zn2+. Spectrochim Acta A Mol Biomol Spectrosc 121:520–526
You GR, Park GJ, Lee SA, Ryu KY, Kim C (2015) Chelate-type Schiff base acting as a colorimetric sensor for iron in aqueous solution. Sensors Actuators B Chem 215:188–195
Kao M-H, Chen T-Y, Cai Y-R, Hu C-H, Liu Y-W, Jhong Y, Wu A-T (2016) A turn-on Schiff-base fluorescence sensor for Mg2+ ion and its practical application. J Lumin 169:156–160
Wu D, Sedgwick AC, Gunnlaugsson T, Akkaya EU, Yoon J, James TD (2017) Fluorescent chemosensors: the past, present and future. Chem Soc Rev 46(23):7105–7123
Ji Y-F, Wang R, Ding S, Du C-F, Liu Z-L (2012) Synthesis, crystal structures and fluorescence studies of three new Zn (II) complexes with multidentate Schiff base ligands. Inorg Chem Commun 16:47–50
Li M, Lu H-Y, Liu R-L, Chen J-D, Chen C-F (2012) Turn-on fluorescent sensor for selective detection of Zn2+, Cd2+, and Hg2+ in water. J Org Chem 77(7):3670–3673
Jiménez-Sánchez A, Ortíz B, Navarrete VO, Farfán N, Santillan R (2015) Two fluorescent Schiff base sensors for Zn 2+: the Zn 2+/Cu 2+ ion interference. Analyst 140(17):6031–6039
Dong W-K, Akogun SF, Zhang Y, Sun Y-X, Dong X-Y (2017) A reversible “turn-on” fluorescent sensor for selective detection of Zn2+. Sensors Actuators B Chem 238:723–734
Sezer H, Ergun E, Ergun Ü (2018) Bis-N, N'(Salisiliden)-1, 4-Bütandiaminin çeşitli metallere karşı gösterdiği floresans özelliklerinin incelenmesi. Düzce Üniversitesi Bilim ve Teknoloji Dergisi 6(4):1163–1177
Choi YW, Park GJ, Na YJ, Jo HY, Lee SA, You GR, Kim C (2014) A single schiff base molecule for recognizing multiple metal ions: a fluorescence sensor for Zn (II) and Al (III) and colorimetric sensor for Fe (II) and Fe (III). Sensors Actuators B Chem 194:343–352
Hirano T, Kikuchi K, Urano Y, Higuchi T, Nagano T (2000) Highly zinc-selective fluorescent sensor molecules suitable for biological applications. J Am Chem Soc 122(49):12399–12400
Wang W, Li R, Song T, Zhang C, Zhao Y (2016) Study on the fluorescent chemosensors based on a series of bis-Schiff bases for the detection of zinc (II). Spectrochim Acta A Mol Biomol Spectrosc 164:133–138
Yan J, Fan L, J-c Q, C-r L, Yang Z-y (2016) A novel and resumable Schiff-base fluorescent chemosensor for Zn (II). Tetrahedron Lett 57(26):2910–2914
Parveen N, Ansari MO, Ahmad MF, Jameel S, Shadab G (2017) Zinc: An element of extensive medical importance. Curr Med Res Pract 7(3):90–98
Boening DW (2000) Ecological effects, transport, and fate of mercury: a general review. Chemosphere 40(12):1335–1351
Kim HN, Ren WX, Kim JS, Yoon J (2012) Fluorescent and colorimetric sensors for detection of lead, cadmium, and mercury ions. Chem Soc Rev 41(8):3210–3244
Su Q, Niu Q, Sun T, Li T (2016) A simple fluorescence turn-on chemosensor based on Schiff-base for Hg2+-selective detection. Tetrahedron Lett 57(38):4297–4301
Ullrich SM, Tanton TW, Abdrashitova SA (2001) Mercury in the aquatic environment: a review of factors affecting methylation. Crit Rev Environ Sci Technol 31(3):241–293
Zhang C, Gao B, Zhang Q, Zhang G, Shuang S, Dong C (2016) A simple Schiff base fluorescence probe for highly sensitive and selective detection of Hg2+ and Cu2+. Talanta 154:278–283
Bayraktutan T, Onganer Y (2017) Biophysical influence of coumarin 35 on bovine serum albumin: Spectroscopic study. Spectrochim Acta A Mol Biomol Spectrosc 171:90–96
Bayraktutan T (2019) Molecular interaction between cationic polymer polyethyleneimine and rose bengal dye: a spectroscopic study. J Turk Chem Soc Sect A Chem 6(3):311–318
EPA (1980) Ambient water criteria for zinc. United States Enviromental Protection Agency Web. https://www.epa.gov/sites/production/files/2018-12/documents/ambient-wqc-zinc.pdf. Accessed 4 May 2020
EPA (2009) National primary drinking water regulation table. United States Enviromental Protection Agency Web. https://www.epa.gov/sites/production/files/2016-06/documents/npwdr_complete_table.pdf. Accessed 4 May 2020
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İnal, E.K. A Fluorescent Chemosensor Based on Schiff Base for the Determination of Zn2+, Cd2+and Hg2+. J Fluoresc 30, 891–900 (2020). https://doi.org/10.1007/s10895-020-02563-6
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DOI: https://doi.org/10.1007/s10895-020-02563-6