Abstract
Herein, we reported the ditriazole Schiff base derivative 1 and evaluated its photophysical properties on induction of varieties of metal ions including Na+, Ag+, Ni2+, Mn2+, Pd2+, Co2+, Hg2+, Cu2+, Pb2+, Cd2+, Zn2+, Sn2+, Fe2+, Fe3+, Cr3+ and Al3+, in order to figure out its potential as ion sensor. The ligand 1 exhibited the strong colorimetric change in the reaction solution as well as absorption spectral shifting with the concomitant appearance of well-defined isosbestic points only upon Co2+, Hg2+ and Cu2+ addition corroborates its applicability as multichannel ion detector. The different extent of spectral shifting as well as unique chromogenic change in the probe solution upon Co2+, Hg2+ and Cu2+ introduction can be used as the discrimination tool for these metal ions. The ligand-metal binding stoichiometry was assessed by their optical response which was further supported by the FT-IR, NMR and mass spectrometric analysis. The association constant and the detection limits of the ligand toward Co2+, Hg2+ and Cu2+ ions were calculated to be 1.52 × 10−8, 3.26 × 10−9, 1.16 × 10−8 and 3.87 × 10−10, 5.47 × 10−11, 8.91 × 10−11 M, respectively, employing the Benesi-Hilderbrand equation and 3 σ slope−1 methods. Furthermore, the successive addition of Co2+, Hg2+ and Cu2+ induce the constant decline in the fluorescence emission signal intensity of the probe. The quenching efficiency of the probe upon metallic induction was fitted to the Stern-Volmer equation which yielded the upward curvature in case of all the three metals ions (Co2+, Hg2+ and Cu2+) when (Io/I-1) was plotted against the quencher concentration indicating the occurrence of both the dynamic and static quenching process in the system with the average Stern-Volmer quenching constant values of 9.25 × 10−7, 1.14 × 10−7, 1.829 × 10−7, respectively.
References
Chan J, Dodani SC, Chang CJ (2012) Reaction-based small-molecule fluorescent probes for chemoselective bioimaging. Nat Chem 4:973–984
Lemke EA, Schultz C (2011) Principles for designing fluorescent sensors and reporters. Nat Chem Biol 7:480–483
Domaille DW, Que EL, Chang CJ (2008) Synthetic fluorescent sensor for studying the cell biology of metals. Nat Chem Biol 4:168–175
Waldron KJ, Rutherford JC, Ford D, Robinson NJ (2009) Metalloprotein and metal sensing. Nature 460:823–830
Cui L, Wu J, Ju H (2014) Nitrogen-doped porous carbon derived from metal − organic gel for electrochemical analysis of heavy-metal ion. ACS Appl Mater Interfaces 6:16210–16216
Shenashen MA, El-Safty SA, Elshehy EA (2014) Monolithic scaffolds for highly selective ion sensing/removal of Co(II), Cu(II), and Cd(II) ions in water. Analyst 139:6393–6405
Xu W, Ren C, Teoh CL, Peng J, Gadre SH, Rhee HW, Lee CLK, Chang YT (2014) An artificial tongue fluorescent sensor array for identification and quantitation of various heavy metal ions. Anal Chem 86:8763–8769
Ghosh K, Sarkar T, Majumdar A (2013) Rhodamine-labelled new architecture for dual sensing of Co2+ and Hg2+ ions. Tetrahedron Lett 54:6464–6468
Cui X, Zhu L, Wu J, Hou Y, Wang P, Wang Z, Yang M (2015) A fluorescent biosensor based on carbon dots-labeled oligo deoxyribonucleotide and graphene oxide for mercury (II) detection. Biosens Bioelectron 63:506–512
Verma R, Gupta BD (2015) Detection of heavy metal ions in contaminated water by surface Plasmon resonance based optical fibre sensor using conducting polymer and chitosan. Food Chem 166:568–575
Ozay H, Kagit R, Yildirim M, Yesilot S, Ozay O (2014) Novel hexapodal triazole linked to a cyclophosphazene core rhodamine-based chemosensor for selective determination of Hg(2+) ions. J Fluoresc 24:1593–1601
Shamsipur M, Sadeghi M, Beyzavi MH, Sharghi H (2015) Development of a novel fluorimetric bulk optode membrane based on meso-tetrakis(2-hydroxynaphthyl) porphyrin (MTHNP) for highly sensitive and selective monitoring of trace amounts of Hg2+ ions. Mater Sci Eng C 48:424–433
Zhou Y, Dong H, Liu L, Li M, Xiao K, Xu M (2014) Selective and sensitive colorimetric sensor of mercury (II) based on gold nanoparticles and 4-mercaptophenylboronic acid. Sensors Actuators B Chem 196:106–111
Du JJ, Jiang L, Shao Q, Liu XG, Marks RS, Ma J, Chen XD (2013) Colorimetric detection of mercury ions based on plasmonic nanoparticles. Small 9:1467–1481
Bhatt KD, Gupte HS, Makwana BA, Vyas DJ, Maity D, Jain VK (2012) Calix receptor edifice; scrupulous turn off fluorescent sensor for Fe(III), Co(II) and Cu(II). J Fluoresc 22:1493–1500
Subhasri A, Anbuselvan C (2014) Facile, cost effective synthesis and DFT-based studies of substituted aryl hydrazones of bdiketones: a new selective fluorescent chemosensor for Co2 +. Anal Methods 6:5596–5609
Cimena O, Dincalp H, Varlıklı C (2015) Studies on UV–Vis and fluorescence changements in Co2+ and Cu2 + recognition by a new benzimidazole–benzothiadiazole derivative. Sensors Actuators B Chem 209:853–863
Gunduz ZY, Gunduz C, Ozpınar C, Urucu OA (2015) A novel Schiff-base as a Cu(II) ion fluorescent sensor in aqueous solution. Spectrochim Acta A Mol Biomol Spectrosc 136:1679–1683
Tedsana W, Tuntulani T, Ngeontae W (2015) A circular dichroism sensor for Ni2+ and Co2+ based on L-cysteine capped cadmium sulfide quantum dots. Anal Chim Acta 867:1–8
Leite FL, Firmino A, Borato CE, Mattoso LHC, da Silva WTL, Jr ONO (2009) Sensor arrays to detect humic substances and Cu(II) in waters. Synth Met 159:2333–2337
Ma Z, Wong KY, Horrigan FT (2008) An extracellular Cu2+ binding site in the voltage sensor of BK and shaker potassium channels. J Gen Physiol 131:483–502
Alpat SK, Alpat S, Kutlu B, Ozbayrak O, Buyukısık HB (2007) Development of biosorption-based algal biosensor for Cu(II) using Tetraselmis chuii. Sensors Actuators B Chem 128:273–278
Marco RD, Martizano J (2008) Response of a copper (II) and iron (III) ion-selective electrode bielectrode array in saline media. Talanta 75:1234–1239
Kim DH, Park YJ, Jung KH, Lee KH (2014) Ratiometric detection of nanomolar concentrations of heparin in serum and plasma samples using a fluorescent chemosensor based on peptides. Anal Chem 86:6580–6586
Yadav UN, Pant P, Sahoo SK, Shankarling GS (2014) A novel colorimetric and fluorogenic chemosensor for selective detection of Cu2+ ions in mixed aqueous media. RSC Adv 4:42647–42653
Ju J, Chen W (2014) Synthesis of highly fluorescent nitrogen-doped graphene quantum dots for sensitive, label-free detection of Fe(III) in aqueous media. Biosens Bioelectron 58:219–225
Li Y, Csok Z, Szuroczki P, Kollar L, Kiss L, Kunsagi-Mate S (2013) Fluorescence quenching studies on the interaction of a novel deepened cavitand towards some transition metal ions. Anal Chim Acta 799:51–56
Acknowledgments
This Research has been performed as a cooperation project of project No. SI1512 (Enhancement of Korea Chemical Bank) and supported by the Korea Research Institute of Chemical Technology (KRICT).
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
ESM 1
(DOCX 1.50 mb)
Rights and permissions
About this article
Cite this article
Saleem, M., Khang, C.H., kim, MH. et al. Chromo/Fluorogenic Detection of Co2+, Hg2+ and Cu2+ by the Simple Schiff Base Sensor. J Fluoresc 26, 11–22 (2016). https://doi.org/10.1007/s10895-015-1723-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-015-1723-x