Rapid and selective detection of fluoride in aqueous solution by a new hemicyanine-based colorimetric and fluorescent chemodosimeter

A novel merocyanine-based chemodosimeter was developed to detect fluoride ions in aqueous solution. This chemodosimeter was found to be a highly selective and sensitive colorimetric and fluorescent sensor for fluoride, and moreover, it shows a fast response within a few minutes to fluoride, thus providing a new and very promising sensor for rapid detection of fluoride in aqueous solution.

[1]  Juyoung Yoon,et al.  A new fluoride selective fluorescent as well as chromogenic chemosensor containing a naphthalene urea derivative. , 2003, Journal of the American Chemical Society.

[2]  F. Gabbaï,et al.  Fluoride ion capture from water with a cationic borane. , 2006, Journal of the American Chemical Society.

[3]  Weihong Zhu,et al.  A near-infrared fluorescence chemodosimeter for fluoride via specific Si–O cleavage , 2012 .

[4]  Xiao-Feng Yang.  Novel fluorogenic probe for fluoride ion based on the fluoride-induced cleavage of tert-butyldimethylsilyl ether. , 2007, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[5]  Subhankar Singha,et al.  In vivo two-photon fluorescent imaging of fluoride with a desilylation-based reactive probe. , 2012, Chemical communications.

[6]  Xianglong Hu,et al.  Reactive Fluorescence Turn-On Probes for Fluoride Ions in Purely Aqueous Media Fabricated from Functionalized Responsive Block Copolymers , 2011 .

[7]  E. Palomares,et al.  Optical mercury sensing using a benzothiazolium hemicyanine dye. , 2006, Organic letters.

[8]  S. Rayalu,et al.  Fluoride in drinking water and defluoridation of water. , 2012, Chemical reviews.

[9]  Félix Sancenón,et al.  Fluorogenic and chromogenic chemosensors and reagents for anions. , 2003, Chemical reviews.

[10]  Hua Lu,et al.  Ratiometric fluorescence chemodosimeters for fluoride anion based on pyrene excimer/monomer transformation. , 2012, Chemical communications.

[11]  Hiroko Matsui,et al.  Some characteristics of fluoride-induced cell death in rat thymocytes: cytotoxicity of sodium fluoride. , 2007, Toxicology in vitro : an international journal published in association with BIBRA.

[12]  Chang-Hee Lee,et al.  Highly sensitive fluorescence "turn-on" indicator for fluoride anion with remarkable selectivity in organic and aqueous media. , 2011, The Journal of organic chemistry.

[13]  K. Rissanen,et al.  Highlights on contemporary recognition and sensing of fluoride anion in solution and in the solid state. , 2013, Chemical Society reviews.

[14]  K. Müllen,et al.  Mesitylboron-substituted ladder-type pentaphenylenes: charge-transfer, electronic communication, and sensing properties. , 2008, Journal of the American Chemical Society.

[15]  L. Toupet,et al.  Naked eye detection of anions by alkynyl-ruthenium exo-receptors: selective recognition of fluoride anion. , 2005, Chemical communications.

[16]  T. Yi,et al.  Highly selective two-photon chemosensors for fluoride derived from organic boranes. , 2005, Organic letters.

[17]  S. Ayoob,et al.  Fluoride in Drinking Water: A Review on the Status and Stress Effects , 2006 .

[18]  Jongmin Park,et al.  Fluorescent probe for detection of fluoride in water and bioimaging in A549 human lung carcinoma cells. , 2009, Chemical communications.

[19]  S. Sharma,et al.  The effect of Pycnogenol on fluoride induced rat kidney lysosomal damage in vitro , 2004, Phytotherapy research : PTR.

[20]  Jong‐In Hong,et al.  Selective anion sensing based on a dual-chromophore approach , 2001 .

[21]  R. Martínez‐Máñez,et al.  Signalling Mechanisms in Anion‐Responsive Push‐Pull Chromophores: The Hydrogen‐Bonding, Deprotonation and Anion‐Exchange Chemistry of Functionalized Azo Dyes , 2007 .

[22]  Yi Li,et al.  A rapid aqueous fluoride ion sensor with dual output modes. , 2010, Angewandte Chemie.

[23]  K. Tamao,et al.  Colorimetric fluoride ion sensing by boron-containing pi-electron systems. , 2001, Journal of the American Chemical Society.

[24]  J. Sessler,et al.  Second Generation Calixpyrrole Anion Sensors , 2000 .

[25]  F. Gabbaï,et al.  Fluoride ion recognition by chelating and cationic boranes. , 2009, Accounts of chemical research.

[26]  K. Venkatasubbaiah,et al.  Luminescent triarylborane-functionalized polystyrene: synthesis, photophysical characterization, and anion-binding studies. , 2006, Journal of the American Chemical Society.

[27]  Jun Feng Zhang,et al.  A highly selective colorimetric and ratiometric two-photon fluorescent probe for fluoride ion detection. , 2011, Organic letters.

[28]  F. Gabbaï,et al.  A BODIPY boronium cation for the sensing of fluoride ions. , 2008, Chemical communications.

[29]  Herschel S Horowitz,et al.  The 2001 CDC recommendations for using fluoride to prevent and control dental caries in the United States. , 2003, Journal of public health dentistry.

[30]  Dongwhan Lee,et al.  Reactivity-based fluoride detection: evolving design principles for spring-loaded turn-on fluorescent probes. , 2007, Organic Letters.

[31]  B. Liu,et al.  A "naked eye" and ratiometric fluorescent chemosensor for rapid detection of F- based on combination of desilylation reaction and excited-state proton transfer. , 2011, Chemical communications.

[32]  Chan Kyung Kim,et al.  Fluoride indicator that functions in mixed aqueous media: hydrogen bonding effects , 2012 .

[33]  Shengju Ou,et al.  Naked-eye detection of fluoride ion in water: a remarkably selective easy-to-prepare test paper. , 2006, Chemical communications.

[34]  Xianshun Zeng,et al.  Novel hemicyanine dye as colorimetric and fluorometric dual-modal chemosensor for mercury in water. , 2011, Organic & biomolecular chemistry.

[35]  Gang Wang,et al.  A ratiometric fluorescent probe for fluoride ion employing the excited-state intramolecular proton transfer. , 2009, Talanta.

[36]  Weiying Lin,et al.  Ratiometric sensing of fluoride anions based on a BODIPY-coumarin platform. , 2011, Organic letters.

[37]  H. Tian,et al.  Fluoride ion-triggered dual fluorescence switch based on naphthalimides winged zinc porphyrin. , 2006, The Journal of organic chemistry.

[38]  Félix Sancenón,et al.  Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the years 2010-2011. , 2011, Chemical Society reviews.

[39]  H. Tian,et al.  A ratiometric fluorescent chemosensor for fluoride ions based on a proton transfer signaling mechanism , 2005 .

[40]  Xiaoling Zhang,et al.  A Highly Selective Colorimetric and “Off-on-off” Fluorescent Probe for Fluoride Ions , 2010, Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.

[41]  T. Swager,et al.  A fluorescent self-amplifying wavelength-responsive sensory polymer for fluoride ions. , 2003, Angewandte Chemie.

[42]  Suning Wang,et al.  Charge-transfer emission in nonplanar three-coordinate organoboron compounds for fluorescent sensing of fluoride. , 2006, Angewandte Chemie.

[43]  Weihong Zhu,et al.  A colorimetric and ratiometric NIR fluorescent turn-on fluoride chemodosimeter based on BODIPY derivatives: high selectivity via specific Si–O cleavage , 2012 .

[44]  F. Gabbaï,et al.  Cationic boranes for the complexation of fluoride ions in water below the 4 ppm maximum contaminant level. , 2009, Journal of the American Chemical Society.

[45]  H. Tian,et al.  A colorimetric and fluorescent chemodosimeter: fluoride ion sensing by an axial-substituted subphthalocyanine , 2005 .

[46]  T. Gunnlaugsson.  Supramolecular chemistry of anionic species themed issue , 2013 .

[47]  E. Akkaya,et al.  Reaction-based sensing of fluoride ions using built-in triggers for intramolecular charge transfer and photoinduced electron transfer. , 2010, Organic letters.

[48]  Xiao-Feng Yang,et al.  A Fluorescein-based Fluorogenic Probe for Fluoride Ion Based on the Fluoride-induced Cleavage of tert-butyldimethylsilyl Ether , 2006, Journal of Fluorescence.

[49]  Philip A. Gale,et al.  Anion receptor chemistry: highlights from 2007. , 2009, Chemical Society reviews.

[50]  M. H. Lee,et al.  Fluoride ion complexation by a cationic borane in aqueous solution. , 2007, Chemical communications.

[51]  Chang-qing Zhu,et al.  A colorimetric method for fluoride determination in aqueous samples based on the hydroxyl deprotection reaction of a cyanine dye , 2005 .

[52]  Shirley Dex,et al.  JR 旅客販売総合システム（マルス）における運用及び管理について , 1991 .

[53]  M. Vázquez,et al.  A colorimetric approach to anion sensing: a selective chemosensor of fluoride ions, in which color is generated by anion-enhanced pi delocalization. , 2004, Angewandte Chemie.

[54]  K. Rissanen,et al.  Recognition and sensing of fluoride anion. , 2009, Chemical communications.

[55]  Jonathan L. Sessler,et al.  Dipyrrolylquinoxalines: Efficient Sensors for Fluoride Anion in Organic Solution , 1999 .

[56]  Hong Zheng,et al.  A colorimetric and fluorescent merocyanine-based probe for biological thiols. , 2009, Organic & biomolecular chemistry.

[57]  C. Wade,et al.  Fluoride ion complexation and sensing using organoboron compounds. , 2010, Chemical reviews.

[58]  Hao Wang,et al.  Design of bis-spiropyran ligands as dipolar molecule receptors and application to in vivo glutathione fluorescent probes. , 2010, Journal of the American Chemical Society.

[59]  B. K. Mishra,et al.  Cyanines during the 1990s: A Review. , 2000, Chemical reviews.

[60]  E. Monzani,et al.  Nature of urea-fluoride interaction: incipient and definitive proton transfer. , 2004, Journal of the American Chemical Society.

[61]  J. Sessler,et al.  Phenanthroline complexes bearing fused dipyrrolylquinoxaline anion recognition sites: efficient fluoride anion receptors. , 2002, Journal of the American Chemical Society.

[62]  David Wypij,et al.  Age-specific Fluoride Exposure in Drinking Water and Osteosarcoma (United States) , 2006, Cancer Causes & Control.

[63]  Jong‐In Hong,et al.  Chromogenic and fluorescent chemodosimeter for detection of fluoride in aqueous solution. , 2007, Organic letters.

[64]  Amitava Das,et al.  Efficient and simple colorimetric fluoride ion sensor based on receptors having urea and thiourea binding sites. , 2004, Organic letters.

[65]  T. Nakanishi,et al.  Aryl-substituted C3-bridged oligopyrroles as anion receptors for formation of supramolecular organogels. , 2007, Journal of the American Chemical Society.

[66]  Manoj Kumar,et al.  Facile cyclization of terphenyl to triphenylene: a new chemodosimeter for fluoride ions. , 2010, Organic letters.

[67]  B. Liu,et al.  A new strategy for highly selective fluorescent sensing of F− and Zn2+ with dual output modes , 2012 .

[68]  T. Gunnlaugsson,et al.  Colorimetric "naked eye" sensing of anions in aqueous solution. , 2005, The Journal of organic chemistry.

[69]  Bin Du,et al.  A highly selective colorimetric and ratiometric fluorescent chemodosimeter for imaging fluoride ions in living cells. , 2011, Chemical communications.

[70]  Philip A. Gale,et al.  Anion Recognition and Sensing: The State of the Art and Future Perspectives. , 2001, Angewandte Chemie.

[71]  Han Na Lee,et al.  A new fluorescein derivative bearing a boronic acid group as a fluorescent chemosensor for fluoride ion. , 2006, The Journal of organic chemistry.