Dual ion selective fluorescence sensor with potential applications in sample monitoring and membrane sensing

Abstract A new sensing functionalized chemosensor 3-hydroxy-2-(1H-indol-3-yl)-4H-chromen-4-one ( M1) was readily prepared in facile reaction conditions and explored its sensing nature response towards metal ions in semi-aqueous medium. The chemosensor M1 exhibited high selective and sensitive fluorescence turn “off-on” response for Al 3+ and Zn 2+ ions in the existence of several metal ions and the changes are enabled for naked-eye detection. These high selectivity expressed by high binding constants 2.62 × 10 4 (Al 3+ ) and 1.92 × 10 4 M −1 (Zn 2+ ) calculated by the Benesi-Hildebrand equation based on the emission studies. The binding strategy was also supported by 1 H NMR titration.

[1]  W. T. Mason,et al.  Fluorescent and luminescent probes for biological activity : a practical guide to technology for quantitative real-time analysis , 1993 .

[2]  Trond Peder Flaten,et al.  Aluminium as a risk factor in Alzheimer’s disease, with emphasis on drinking water , 2001, Brain Research Bulletin.

[3]  Ying Zhou,et al.  A novel sensitive turn-on fluorescent Zn2+ chemosensor based on an easy to prepare C3-symmetric Schiff-base derivative in 100% aqueous solution. , 2012, Organic letters.

[4]  T. Mak,et al.  A quinolinyl antipyrine based fluorescence sensor for Zn2+ and its application in bioimaging , 2012 .

[5]  S. Mashraqui,et al.  A new internal charge transfer probe for the highly selective detection of Zn(II) by means of dual colorimetric and fluorescent turn-on responses , 2012 .

[6]  Y. Urano,et al.  Development of an iminocoumarin-based zinc sensor suitable for ratiometric fluorescence imaging of neuronal zinc. , 2007, Journal of the American Chemical Society.

[7]  L. Kosta,et al.  A highly selective diethyldithiocarbamate extraction system in activation analysis of copper, indium, manganese and zinc , 1974 .

[8]  Naveen Mergu,et al.  A new multifunctional rhodamine-derived probe for colorimetric sensing of Cu(II) and Al(III) and fluorometric sensing of Fe(III) in aqueous media , 2016 .

[9]  M. Gharpure,et al.  Synthesis of new series of 3-hydroxy/acetoxy-2-phenyl-4H-chromen-4-ones and their biological importance , 2013, Journal of Chemical Sciences.

[10]  Y. Zhang,et al.  1,8-Naphthyridine-based molecular clips for off–on fluorescence sensing of Zn2+ in living cells , 2015 .

[11]  Shishen Zhang,et al.  A reactive probe for Cu2+ based on the ESIPT mechanism and its application in live-cell imaging , 2015 .

[12]  Hsiang-Yi Lin,et al.  A turn-on and reversible fluorescence sensor for zinc ion. , 2012, The Analyst.

[13]  H. Yoshida,et al.  Effective recovery of harmful metal ions from squid wastes using subcritical and supercritical water treatments. , 2005, Environmental science & technology.

[14]  Ashutosh Kumar Singh,et al.  Fluorescent chemosensors for Zn2+ ions based on flavonol derivatives , 2014 .

[15]  Ashutosh Kumar Singh,et al.  A novel optical sensor for copper ions based on phthalocyanine tetrasulfonic acid , 2015 .

[16]  Ashutosh Kumar Singh,et al.  Antipyrine based Schiff bases as Turn-on Fluorescent sensors for Al (III) ion , 2014 .

[17]  Ashutosh Kumar Singh,et al.  Thiazole Schiff base turn-on fluorescent chemosensor for Al3+ ion , 2014 .

[18]  H. Y. Jo,et al.  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) , 2014 .

[19]  Ashutosh Kumar Singh,et al.  A turn-on fluorescent chemosensor for Zn2+ ions based on antipyrine schiff base , 2014 .

[20]  H. Y. Jo,et al.  A single chemosensor for multiple analytes: fluorogenic detection of Zn2+ and OAc− ions in aqueous solution, and an application to bioimaging , 2014 .

[21]  A. Jain,et al.  Aluminum(III) selective potentiometric sensor based on morin in poly(vinyl chloride) matrix. , 2007, Talanta.

[22]  H. Hara,et al.  Speciation of aluminum in rainwater using a fluoride ion-selective electrode and ion-exchange chromatography with fluorometric detection of the aluminum-lumogallion complex. , 2001, Analytical chemistry.

[23]  M. R. Binet,et al.  Detection and characterization of zinc- and cadmium-binding proteins in Escherichia coli by gel electrophoresis and laser ablation-inductively coupled plasma-mass spectrometry. , 2003, Analytical biochemistry.

[24]  Ying Xu,et al.  A highly selective fluorescence-based polymer sensor incorporating an (R,R)-salen moiety for Zn(2+) detection. , 2010, Chemistry.

[25]  Ashutosh Kumar Singh,et al.  Selective naked-eye detection of Magnesium (II) ions using a coumarin-derived fluorescent probe , 2015 .

[26]  I. Leray,et al.  Design principles of fluorescent molecular sensors for cation recognition , 2000 .

[27]  Q. Guo,et al.  6-Substituted quinoline-based ratiometric two-photon fluorescent probes for biological Zn2+ detection. , 2012, Chemical communications.

[28]  Baodui Wang,et al.  Design and synthesis of a chemosensor for the detection of Al3+ based on ESIPT , 2014 .

[29]  K. S. Subramanian,et al.  Aluminium in drinking water: An overview , 1999 .

[30]  Roger Y. Tsien,et al.  Fluorescent and Photochemical Probes of Dynamic Biochemical Signals inside Living Cells , 1993 .

[31]  Vinod K. Gupta,et al.  Novel Furochromenone based Dual Channel Sensors for Selective Detection of Cu2+ with Potential Applications in Sample Monitoring, Membrane Sensing and Photo–printing , 2016 .

[32]  Keh-Feng Huang,et al.  A new pyrene-based Schiff-base: a selective colorimetric and fluorescent chemosensor for detection of Cu(II) and Fe(III). , 2014, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[33]  M. Asif,et al.  Novel synthesized antipyrine derivative based “Naked eye” colorimetric chemosensors for Al3+ and Cr3+ , 2016 .

[34]  A. Jain,et al.  An iron(III) ion-selective sensor based on a mu-bis(tridentate) ligand. , 2007, Talanta.

[35]  Joel H. Hildebrand,et al.  A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons , 1949 .

[36]  Jianrong Chen,et al.  Determination of cadmium, copper, lead and zinc in water samples by flame atomic absorption spectrometry after cloud point extraction , 2001 .

[37]  Sudhir Kumar Shoora,et al.  A simple Schiff base based novel optical probe for aluminium (III) ions , 2015 .

[38]  Vinod K. Gupta,et al.  2-(Alkylamino)-3-aryl-6,7-dihydrobenzofuran-4(5H)-ones: Improved Synthesis and their Photophysical Properties , 2015, ChemistryOpen.

[39]  Quan-min Li,et al.  The determination of zinc in water by flame atomic absorption spectrometry after its separation and preconcentration by malachite green loaded microcrystalline triphenylmethane , 2007 .

[40]  Ashutosh Kumar Singh,et al.  An easily accessible switch-on optical chemosensor for the detection of noxious metal ions Ni(II), Zn(II), Fe(III) and UO2(II) , 2016 .

[41]  Terence E. Rice,et al.  Signaling Recognition Events with Fluorescent Sensors and Switches. , 1997, Chemical reviews.

[42]  Ashutosh Kumar Singh,et al.  A novel gadolinium ion-selective membrane electrode based on 2-(4-phenyl-1, 3-thiazol-2-yliminomethyl) phenol , 2013 .

[43]  Vinod K. Gupta,et al.  An easily accessible optical chemosensor for Cu2+ based on novel imidazoazine framework, its performance characteristics and potential applications , 2017 .

[44]  Dilip K. Maiti,et al.  A new pyridoxal based fluorescence chemo-sensor for detection of Zn(II) and its application in bio imaging , 2015 .

[45]  Zuobing Xiao,et al.  Determination of aluminum in foods by stabilized temperature platform graphite furnace atomic absorption spectrometry , 1991 .

[46]  Bin Tong,et al.  A novel "turn-on" fluorescent chemosensor for the selective detection of Al3+ based on aggregation-induced emission. , 2012, Chemical communications.

[47]  Jae Jun Lee,et al.  A highly selective turn-on chemosensor capable of monitoring Zn2+ concentrations in living cells and aqueous solution , 2015 .

[48]  Alok Pandya,et al.  An ICT based "turn on/off" quinoline armed calix[4]arene fluoroionophore: its sensing efficiency towards fluoride from waste water and Zn2+ from blood serum. , 2012, The Analyst.

[49]  Zheng-yin Yang,et al.  Design of a novel coumarin-based multifunctional fluorescent probe for Zn²⁺/Cu²⁺/S²⁻ in aqueous solution. , 2015, Materials science & engineering. C, Materials for biological applications.

[50]  Ashutosh Kumar Singh,et al.  A reversible fluorescence "off-on-off" sensor for sequential detection of aluminum and acetate/fluoride ions. , 2015, Talanta.

[51]  Guoqiang Yang,et al.  A potential fluorescent sensor for Zn2+ based on a selective bis-9-anthryldiamine ligand operating in buffer , 2006 .

[52]  A. Banerjee,et al.  A coumarin-based "turn-on" fluorescent sensor for the determination of Al3+: single crystal X-ray structure and cell staining properties. , 2013, Dalton transactions.

[53]  M. Ghaedi,et al.  Preparation of Iodide Selective Carbon Paste Electrode with Modified Carbon Nanotubes by Potentiometric Method and Effect of CuS‐NPs on Its Response , 2015 .

[54]  M. Pei,et al.  A fluorescence chemosensor based on imidazo[1,2-a]quinoline for Al3+ and Zn2+ in respective solutions , 2015 .