A New Polymer-Based Fluorescent Chemosensor Incorporating Propane-1,3-Dione and 2,5-Diethynylbenzene Moieties for Detection of Copper(II) and Iron(III)

A novel conjugated polymer (PDBDBM) was developed by the polymerization of 1,4-dioctyloxy-2,5-diethynylbenzene with 1,3-bis(4-bromophenyl)propane-1,3-dione based on Pd-catalyzed Sonogashira-coupling reaction. The obtained polymer PDBDBM exhibited bright green photoluminescence under UV irradiation. According to the metal ion titration experiments, PDBDBM showed high sensitivity and selectivity for detection of Cu2+ and Fe3+ over other metal ions. The fluorescent detection limits of PDBDBM were calculated to be 5 nM for Cu2+ and 0.4 μM for Fe3+ and the Stern–Volmer quenching constant for Cu2+ and Fe3+ were found to be 1.28 × 108 M−1 and 2.40 × 104 M−1, respectively. These results indicated that the polymer can be used as a potential probe for Cu2+ and Fe3+ detection.

[1]  J. Štupar,et al.  Determination of iron species in wine by ion-exchange chromatography--flame atomic absorption spectrometry. , 1989, The Analyst.

[2]  Yixiang Cheng,et al.  In Situ Generated 1:1 Zn(II)-Containing Polymer Complex Sensor for Highly Enantioselective Recognition of N-Boc-Protected Alanine , 2012 .

[3]  Yong Cao,et al.  Synthesis, Characterization, and Photophysics of Electroluminescent Copolymers with a Quinoline-Based Iridium Complex in the Main Chain: A Versatile Method for Constructing Metal-Containing Copolymers , 2007 .

[4]  Dibakar Dhara,et al.  Water-soluble polymeric chemosensor for detection of Cu2+ ions with high selectivity and sensitivity , 2016 .

[5]  Xin Liu,et al.  Sensitive and selective rhodamine-derived probes for fluorometric sensing of pH and colorimetric sensing of Cu2+ , 2017 .

[6]  He Tian,et al.  Recent progress on polymer-based fluorescent and colorimetric chemosensors. , 2011, Chemical Society reviews.

[7]  Zhiqiang Shi,et al.  Cationic conjugated polyelectrolyte-based fluorometric detection of copper(II) ions in aqueous solution , 2008 .

[8]  Xunhua Liu,et al.  Fluorescence Study of Chiral β‐Ketoiminate‐Based Newly Synthesized Boron Hybrid Polymers , 2014 .

[9]  A. H. Malik,et al.  An anionic conjugated polymer as a multi-action sensor for the sensitive detection of Cu(2+) and PPi, real-time ALP assaying and cell imaging. , 2015, The Analyst.

[10]  Chunlei Zhu,et al.  Conjugated polymer nanoparticles: preparation, properties, functionalization and biological applications. , 2013, Chemical Society reviews.

[11]  John F. Callan,et al.  Iron(III) selective molecular and supramolecular fluorescent probes. , 2012, Chemical Society reviews.

[12]  Yu Wang,et al.  1,4-Dihydroxyanthraquinone–Cu2+ ensemble probe for selective detection of sulfide anion in aqueous solution , 2013 .

[13]  Lianhui Wang,et al.  AIE-active conjugated polymer nanoparticles with red-emission for in vitro and in vivo imaging , 2016 .

[14]  Yanhong Xu,et al.  Controlled synthesis of conjugated microporous polymer films: versatile platforms for highly sensitive and label-free chemo- and biosensing. , 2014, Angewandte Chemie.

[15]  Satish Kumar,et al.  Photochromic spirooxazine as highly sensitive and selective probe for optical detection of Fe 3+ in aqueous solution , 2016 .

[16]  J. Qin,et al.  An imidazole-functionalized polyacetylene: convenient synthesis and selective chemosensor for metal ions and cyanide. , 2008, Chemical communications.

[17]  Yixiang Cheng,et al.  Polymer-based fluorescence sensor incorporating thiazole moiety for direct and visual detection of Hg2+ and Ag+ , 2015 .

[18]  Jingjing Li,et al.  Design and synthesis of a highly sensitive “Turn-On” fluorescent organic nanoprobe for iron(III) detection and imaging , 2014 .

[19]  Najun Li,et al.  A polymeric chemosensor for Fe3+ based on fluorescence quenching of polymer with quinoline derivative in the side chain , 2009 .

[20]  Nataliya V. Roznyatovskaya,et al.  Conducting polymers in chemical sensors and arrays. , 2008, Analytica chimica acta.

[21]  Yi Xiao,et al.  Ratiometric and selective fluorescent sensor for CuII based on internal charge transfer (ICT). , 2005, Organic letters.

[22]  Yuyang Jiang,et al.  A dual-response quinoline-based fluorescent sensor for the detection of Copper (II) and Iron(III) ions in aqueous medium , 2017 .

[23]  T. Swager,et al.  Conjugated Polymer‐Based Chemical Sensors , 2000 .

[24]  Lu Jin,et al.  Fluorescence turn-on detection of Fe3+ in pure water based on a cationic poly(perylene diimide) derivative , 2016 .

[25]  Amy E. Palmer,et al.  Fluorescent Sensors for Measuring Metal Ions in Living Systems , 2014, Chemical reviews.

[26]  Xuediao Cai,et al.  Hyperbranched conjugated polymers containing 1,3-butadiene units: metal-free catalyzed synthesis and selective chemosensors for Fe3+ ions , 2017 .

[27]  Hongying Lv,et al.  Ultra-high sensitive voltammetric sensor modified by largely oxygenous functionalized ultrathin carbon nitride nanosheets for detection of Cu (II) , 2017 .

[28]  Shouxiang Jiang,et al.  Polythiophene based fluorescent probe for copper ions with high sensitivity , 2015 .

[29]  H. Tong,et al.  Phosphonate-Functionalized Polyfluorene Film Sensors for Sensitive Detection of Iron(III) in both Organic and Aqueous Media , 2010 .

[30]  Jing Xie,et al.  Synthesis, characterization, photophysical and oxygen-sensing properties of a novel europium(III) complex. , 2010, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[31]  Zhimin Luo,et al.  Conjugated polymer nanoparticles with aggregation induced emission characteristics for intracellular Fe3+ sensing , 2016 .

[32]  A. Maity,et al.  N, N coordinating schiff base ligand acting as a fluorescence sensor for zinc(II) and colorimetric sensor for copper(II), and zinc(II) in mixed aqueous media , 2014 .

[33]  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 .

[34]  C. Yin,et al.  Highly sensitive and selective fluorescent probe for determination of Cu(II) in aqueous solution , 2014 .

[35]  Rong-Yi Huang,et al.  Turn-on fluorogenic and chromogenic detection of Fe3+ and Cr3+ in a completely water medium with polyacrylamide covalently bonding to rhodamine B using diethylenetriamine as a linker , 2014 .

[36]  Cheng Gu,et al.  Design of Highly Photofunctional Porous Polymer Films with Controlled Thickness and Prominent Microporosity , 2015, Angewandte Chemie.

[37]  Yuanpeng Wang,et al.  The influence of soil heavy metals pollution on soil microbial biomass, enzyme activity, and community composition near a copper smelter. , 2007, Ecotoxicology and environmental safety.

[38]  Parameswar Krishnan Iyer,et al.  Aqueous polyfluorene probe for the detection and estimation of Fe3+ and inorganic phosphate in blood serum , 2011 .

[39]  Yixiang Cheng,et al.  A highly selective and sensitive polymer-based OFF-ON fluorescent sensor for Hg2+ detection incorporating salen and perylenyl moieties , 2012 .

[40]  K. Schanze,et al.  Conjugated Polyelectrolytes: Synthesis, Photophysics, and Applications , 2009 .

[41]  D. Thiele,et al.  Copper: An essential metal in biology , 2011, Current Biology.

[42]  Jetty L. Duffy-Matzner,et al.  Pentiptycene-Derived Fluorescence Turn-Off Polymer Chemosensor for Copper(II) Cation with High Selectivity and Sensitivity , 2017, Polymers.

[43]  Xiaodong Yang,et al.  Thiourea based conjugated polymer fluorescent chemosensor for Cu+ and its use for the detection of hydrogen peroxide and glucose , 2016, Chinese Journal of Polymer Science.

[44]  B. MacCraith,et al.  Characterisation of porosity and sensor response times of sol–gel-derived thin films for oxygen sensor applications , 2002 .

[45]  Juyoung Yoon,et al.  Fluorescent probes and bioimaging: alkali metals, alkaline earth metals and pH. , 2015, Chemical Society reviews.

[46]  Yixiang Cheng,et al.  Polymer-based fluorescent sensor incorporating 2,2′-bipyridyl and benzo[2,1,3]thiadiazole moieties for Cu2+ detection , 2011 .

[47]  Ge Zhang,et al.  Facile fabrication of a cost-effective, water-soluble, and electrosynthesized poly(9-aminofluorene) fluorescent sensor for the selective and sensitive detection of Fe(III) and inorganic phosphates , 2012 .

[48]  Luyong Zhang,et al.  A new selective fluorescent chemical sensor for Fe3+ based on rhodamine B and a 1,4,7,10-tetraoxa-13-azacyclopentadecane conjugate and its imaging in living cells , 2015 .

[49]  Richard F Hurrell,et al.  Nutritional iron deficiency , 2007, The Lancet.

[50]  R. Mckenzie.  The adsorption of lead and other heavy metals on oxides of manganese and iron , 1980 .

[51]  Lianhui Wang,et al.  Water‐soluble hyperbranched polyelectrolytes with high fluorescence quantum yield: Facile synthesis and selective chemosensor for Hg2+ and Cu2+ ions , 2010 .