Coumarin Based Highly Selective “off-on-off” Type Novel Fluorescent Sensor for Cu2+ and S2− in Aqueous Solution

AbstractSolvent free synthesis of 6,7-dihydroxy-3-(3-chlorophenyl) coumarin (CFHC) was designed and obtained by the interaction of 2-(2,4,5-trimethoxyphenyl)-1-(3-chlorophenyl)acrylonitrile with pyridinium hydrochloride in the presence of silica gel by using microwave irradiation. The characterization of CFHC was confirmed by FT-IR, 1H, 13C, 13C–APT and 2D HETCOR spectroscopy methods. The optical behavior of CFHC towards metal ions was investigated by UV-visible and fluorescence spectroscopy. CFHC showed “on–off” type fluorescence response towards Cu2+ with high selectivity in aqueous solution (CH3CN/H2O, 9/1, v/v). Once binding with Cu2+, CFHC-Cu2+ complex also displayed high selectivity for sulfide, resulting in “off–on” type sensing of sulfide anion. Graphical abstractVisual fluorescence changes upon addition of various metal ions (5.0 eq.) to CFHC in CH3CN/H2O (90:10, v/v) under UV excitation (365 nm)

[1]  A. Agostino,et al.  Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy , 2014 .

[2]  A Novel Highly Sensitive and Selective Fluorescent Sensor for Imaging Copper (II) in Living Cells , 2014, Journal of Fluorescence.

[3]  Jinquan Yang,et al.  A nano-copper electrochemical sensor for sensitive detection of chemical oxygen demand , 2011 .

[4]  Maurizio Licchelli,et al.  Transition Metals as Switches , 1999 .

[5]  Shu-Pao Wu,et al.  A Pyrene-based Highly Selective Turn-on Fluorescent Chemosensor for Iron(III) Ions and its Application in Living Cell Imaging , 2013, Journal of Fluorescence.

[6]  Yavuz Dede,et al.  A fluorescent coumarin-thiophene hybrid as a ratiometric chemosensor for anions: Synthesis, photophysics, anion sensing and orbital interactions , 2016 .

[7]  A. Ramanavičius,et al.  Electrochemical copper (II) sensor based on self-assembled 4-amino-6-hydroxy-2-mercaptopyrimidine monohydrate , 2011 .

[8]  J. Sarkar,et al.  Simple and efficient coumarin-based colorimetric and fluorescent chemosensor for F− detection: An ON1–OFF–ON2 fluorescent assay , 2016 .

[9]  Kasi Pitchumani,et al.  β-Cyclodextrin included coumarin derivatives as selective fluorescent sensors for Cu2+ ions in HeLa cells , 2016 .

[10]  C. Redshaw,et al.  A single chemosensor for multiple analytes: fluorogenic and ratiometric absorbance detection of Zn²⁺, Mg²⁺ and F⁻, and its cell imaging , 2016 .

[11]  Yong Ye,et al.  A Rhodamine-Cyclen Conjugate as Chromogenic and Fluorescent Chemosensor for Copper Ion in Aqueous Media , 2013, Journal of Fluorescence.

[12]  Jingli Yuan,et al.  Development of a heterobimetallic Ru(II)-Cu(II) complex for highly selective and sensitive luminescence sensing of sulfide anions. , 2011, Analytica chimica acta.

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

[14]  Dan Li,et al.  A two-in-one fluorescent sensor with dual channels to detect Zn2+ and Cd2+ , 2013 .

[15]  Fengting Lü,et al.  Fluorescent film sensor for copper ion based on an assembled monolayer of pyrene moieties. , 2011, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[16]  S. Tekin,et al.  Synthesis, structural characterization, and in vitro anti-cancer activities of new phenylacrylonitrile derivatives , 2016, Applied Biological Chemistry.

[17]  J. Qin,et al.  Displacement method to develop highly sensitive and selective dual chemosensor towards sulfide anion. , 2011, The Analyst.

[18]  Guonan Chen,et al.  Determination of copper(II) in the dairy product by an electrochemical sensor based on click chemistry. , 2011, Analytica chimica acta.

[19]  Jae Jun Lee,et al.  Experimental and theoretical studies for sequential detection of copper(II) and cysteine by a colorimetric chemosensor , 2016 .

[20]  Haijun Chen,et al.  Design, synthesis and biological evaluation of a novel Cu2+-selective fluorescence sensor for bio-detection and chelation , 2015 .

[21]  R. Martínez‐Máñez,et al.  A new chromo-chemodosimeter selective for sulfide anion. , 2003, Journal of the American Chemical Society.

[22]  Ying Yu,et al.  Two Schiff base ligands for distinguishing ZnII/CdII sensing—effect of substituent on fluorescent sensing , 2015 .

[23]  Shu-Pao Wu,et al.  A Pyrene-based Highly Selective Turn-on Fluorescent Sensor for Copper(II) Ion and its Application in Live Cell Imaging , 2011, Journal of Fluorescence.

[24]  M. Pei,et al.  Novel fluorescent sensors based on benzimidazo[2,1-a]benz[de]isoquinoline-7-one-12-carboxylic acid for Cu2+ , 2014 .

[25]  Shu-Pao Wu,et al.  An NBD-based Sensitive and Selective Fluorescent Sensor for Copper(II) Ion , 2011, Journal of Fluorescence.

[26]  Zhen Li,et al.  An indirect approach for anion detection: the displacement strategy and its application. , 2012, Chemical communications.

[27]  Xianfu Lin,et al.  A novel inhibition biosensor constructed by layer-by-layer technique based on biospecific affinity for the determination of sulfide , 2008 .

[28]  Liancheng Zhao,et al.  A Highly Selective Turn-on Fluorescent Chemodosimeter for Cu2+ Through a Cu2+-Promoted Redox Reaction , 2014, Journal of Fluorescence.

[29]  Shu-Pao Wu,et al.  A highly selective turn-on fluorescence chemosensor for Hg(II) and its application in living cell imaging , 2014 .

[30]  Zan Li,et al.  Multifunctional BODIPY derivatives to image cancer cells and sense copper(II) ions in living cells , 2013 .

[31]  P. Singh,et al.  Coumarin–pyrene conjugate: Synthesis, structure and Cu-selective fluorescent sensing in mammalian kidney cells , 2016 .

[32]  G. Das,et al.  Fluorescence Turn on Sensor for Sulfate Ion in Aqueous Medium Using Tripodal-Cu2+ Ensemble , 2014, Journal of Fluorescence.

[33]  Hossein Tavallali,et al.  Colorimetric detection of copper and chloride in DMSO/H₂O media using bromopyrogallol red as a chemosensor with analytical applications. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[34]  W. Shen,et al.  A General Chemical Conversion Route To Synthesize Various ZnO-Based Core/Shell Structures , 2008 .

[35]  Xiaowen Xu,et al.  Highly specific colorimetric recognition and sensing of sulfide with glutathione-modified gold nanoparticle probe based on an anion-for-molecule ligand exchange reaction. , 2012, The Analyst.

[36]  Lingwen Zeng,et al.  A simple and sensitive sensor for rapid detection of sulfide anions using DNA-templated copper nanoparticles as fluorescent probes. , 2012, The Analyst.

[37]  M. Chan,et al.  Direct determination of cadmium and copper in seawater using a transversely heated graphite furnace atomic absorption spectrometer with Zeeman-effect background corrector. , 2000, Talanta.

[38]  J. Qin,et al.  A New Disubstituted Polyacetylene Bearing Pyridine Moieties: Convenient Synthesis and Sensitive Chemosensor toward Sulfide Anion with High Selectivity , 2011 .

[39]  Youngkwan Lee,et al.  Electrochemical detection of copper ion using a modified copolythiophene electrode , 2009 .

[40]  Kejian Yao,et al.  A fluorescence on–off sensor for Cu2+ and its resultant complex as an off–on sensor for Cr3+ in aqueous media , 2015 .

[41]  S. Bari,et al.  Luminescent Eu(III) hybrid sensors for in situ copper detection , 2011 .

[42]  B. Liu,et al.  A colorimetric and ratiometric turn-on BODIPY-based fluorescent probe for double-channel detection of Cu2+ and Hg2+ , 2013 .