Colorimetric and fluorescent probes for real-time naked eye sensing of copper ion in solution and on paper substrate

In this paper, BT ((E)-2-(4-(4-(bis(pyridin-2-ylmethyl)amino)styryl)-3-cyano-5,5-dimethylfuran-2(5H)-ylidene)malononitrile) with strong donor–π-acceptor structure was synthesized, which showed both colorimetric and fluorescent sensing ability toward Cu2+ with high selectivity and sensitivity. Job plot and mass spectra measurement revealed a 1 : 1 coordination mode between Cu2+ and probe BT in ethanol/HEPES (1 : 4 v/v) buffer (pH 7.2) solution, and the binding constant was calculated to be 3.6 × 104 M–1. The colour of BT solution (10 µM) immediately turned from purple red to yellow and the red fluorescence was quenched obviously when a certain amount of Cu2+ was added, which enabled a dual-channel detection of Cu2+. A paper strip pre-stained with BT solution was further fabricated and it also showed excellent sensing ability toward Cu2+ with a detection limit as low as 10−6 M with the naked eye, which represents better portability and operation simplicity that is favourable for on-site analysis of Cu2+ in water.

[1]  A. Jabbari,et al.  Biologically green synthesized silver nanoparticles as a facile and rapid label-free colorimetric probe for determination of Cu2+ in water samples. , 2017, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[2]  P. He,et al.  A new hydroxynaphthyl benzothiazole derived fluorescent probe for highly selective and sensitive Cu(2+) detection. , 2016, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[3]  Qingyan Zhang,et al.  A simple Schiff base fluorescence probe for highly sensitive and selective detection of Hg(2+)and Cu(2.). , 2016, Talanta.

[4]  Jinheung Kim,et al.  A Solvent-dependent Fluorogenic Probe Containing Julolidine for Cr(III) and Cu(II) , 2016 .

[5]  Fei Wu,et al.  An NIR Molecule-based “On–Off” Fluorescent and Colorimetric Sensor for Cyanide Anions , 2016 .

[6]  S. H. Park,et al.  Cadmium(II) complexes containing N′-substituted N,N-di(2-picolyl)amine: The formation of monomeric versus dimeric complexes is affected by the N′-substitution group on the amine moiety , 2015 .

[7]  Xuchun Wang,et al.  A rhodamine-based fluorescent probe for Cu(II) determination in aqueous solution. , 2015, Luminescence : the journal of biological and chemical luminescence.

[8]  N. Dey,et al.  Exclusive detection of sub-nanomolar levels of palladium(II) in water: an excellent probe for multiple applications. , 2014, Chemistry, an Asian journal.

[9]  Ya Cao,et al.  Development of a fast responsive and highly sensitive fluorescent probe for Cu2+ ion and imaging in living cells , 2014 .

[10]  Dan Du,et al.  Nanomaterial-enhanced paper-based biosensors , 2014 .

[11]  Wei Wang,et al.  A highly selective turn-off fluorescent probe for Cu(II) based on a dansyl derivative and its application in living cell imaging , 2014 .

[12]  Yi-Chang Chen,et al.  Self-assembled tetraphenylethylene macrocycle nanofibrous materials for the visual detection of copper(II) in water , 2014 .

[13]  Xiao‐Qi Yu,et al.  A water-soluble near-infrared probe for colorimetric and ratiometric sensing of SO2 derivatives in living cells. , 2014, Chemical communications.

[14]  Xiaoming Yang,et al.  Synthesis of highly fluorescent lysine-stabilized Au nanoclusters for sensitive and selective detection of Cu2+ ion , 2013 .

[15]  J. Qin,et al.  A water-soluble two-photon fluorescent turn-on probe for pyrophosphate anion: Design, synthesis and properties , 2013 .

[16]  Anmin Zheng,et al.  Combined spectral experiment and theoretical calculation to study the chemosensors of copper and their applications in anion bioimaging , 2013 .

[17]  Claudio Parolo,et al.  Paper-based nanobiosensors for diagnostics. , 2013, Chemical Society reviews.

[18]  Y. Guan,et al.  Colorimetric and "turn-on" fluorescent determination of Cu2+ ions based on rhodamine-quinoline derivative. , 2012, The Analyst.

[19]  Xiao‐Qi Yu,et al.  BINOL-based fluorescent sensor for recognition of Cu(II) and sulfide anion in water. , 2012, The Journal of organic chemistry.

[20]  Sung-Hoon Kim,et al.  A colorimetric and fluorescent chemosensor for Ni2+ based on donor-pi-acceptor charge transfer dye containing 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran acceptor and 4-bis(pyridin-2-ylmethyl)aminobenzene donor. , 2012, Journal of nanoscience and nanotechnology.

[21]  C. Zhong,et al.  A ratiometric fluorescent chemodosimeter with selective recognition for sulfite in aqueous solution. , 2009, The Journal of organic chemistry.

[22]  H. Tian,et al.  A colorimetric and fluorescent turn-on sensor for pyrophosphate anion based on a dicyanomethylene-4H-chromene framework. , 2008, Chemical communications.

[23]  J. Qin,et al.  Novel fluorene-based copolymer with pendant aza-crown ether: Highly sensitive and specific detection for CuSO4 and concurrent effect of anions , 2008 .

[24]  Dylan W Domaille,et al.  Synthetic fluorescent sensors for studying the cell biology of metals. , 2008, Nature chemical biology.

[25]  L. Vendier,et al.  Preparation and study of new poly-8-hydroxyquinoline chelators for an anti-Alzheimer strategy. , 2008, Chemistry.

[26]  H. Kozłowski,et al.  Copper homeostasis and neurodegenerative disorders (Alzheimer's, prion, and Parkinson's diseases and amyotrophic lateral sclerosis). , 2006, Chemical reviews.

[27]  Colin L. Masters,et al.  Neurodegenerative diseases and oxidative stress , 2004, Nature Reviews Drug Discovery.

[28]  B. Sarkar,et al.  Treatment of Wilson and menkes diseases. , 1999, Chemical reviews.

[29]  D. Radisky,et al.  Regulation of Transition Metal Transport across the Yeast Plasma Membrane* , 1999, The Journal of Biological Chemistry.

[30]  H. P. Wu.  Dynamics and performance of fast linear scan anodic stripping voltammetry of cd, pb, and cu using in situ-generated ultrathin mercury films. , 1996, Analytical chemistry.