A sensitive and selective BINOL based ratiometric fluorescence sensor for the detection of cyanide ions

A highly selective, novel BINOL based sensor BBCN has been developed for the fluorescent ratiometric detection of cyanide ions (CN−). The optical study revealed that BBCN exhibited unique spectral changes only with cyanide ions in the presence of other competing ions. Besides, an apparent fluorescent colour change from green to blue was observed. A clear linear relationship was observed between the fluorescence ratiometric ratio of BBCN and the concentration of CN− with a reasonably low detection limit (LOD) of 189 nM (507 ppb). The optical response was due to the nucleophilic addition of CN− to the dicyanovinyl group of the sensor, which compromises the probe's intramolecular charge transfer. This mechanism was well confirmed by Job's plot, 1H-NMR and ESI-MS studies. BBCN showed immediate spectral response towards (1 second) CN− and detection could be realized in a broad pH window. Furthermore, the practical utility of BBCN was studied by test paper-based analysis and the detection of CN− in various water resources.

[1]  Yongbin Zhang,et al.  Boron fluoride regulated “naked eye” and ratiometric fluorescent detection of CN− as a test strip and its bioimaging , 2021 .

[2]  Kerem Kaya,et al.  A highly sensitive and selective fluorescent turn-on chemosensor bearing a 7-diethylaminocoumarin moiety for the detection of cyanide in organic and aqueous solutions , 2020, New Journal of Chemistry.

[3]  Yaoxian Li,et al.  A new highly selective fluorescent sensor based on a novel fluorophore for cyanide and its applications in bioimaging. , 2020, Luminescence : the journal of biological and chemical luminescence.

[4]  Alexis Tigreros,et al.  Cyanide chemosensors based on 3-dicyanovinylpyrazolo[1,5-a]pyrimidines: Effects of peripheral 4-anisyl group substitution on the photophysical properties. , 2020, Talanta.

[5]  Wenlin Feng,et al.  Development of BINOL-Si complexes with large stokes shifts and their application as chemodosimeters for nerve agent , 2020 .

[6]  J. Myśliwiec,et al.  Solvatochromic fluorophores based on thiophene derivatives for highly-precise water, alcohols and dangerous ions detection , 2020 .

[7]  Zhiyun Zhang,et al.  A novel colorimetric and fluorometric probe for the detection of CN− with high selectivity in aqueous media , 2020 .

[8]  Serkan Erdemir,et al.  Phenanthroimidazole and dicyanovinyl-substituted triphenylamine for the selective detection of CN−: DFT calculations and practically applications , 2020 .

[9]  Serkan Erdemir,et al.  Red and blue emitting fluorescent probe for cyanide and hypochlorite ions: Biological sensing and environmental analysis , 2020 .

[10]  R. Navarro,et al.  Adamantyl-BINOL as platform for chiral porous polymer aromatic frameworks. Multiple applications as recyclable catalysts , 2019, Journal of Catalysis.

[11]  X. Cui,et al.  A colorimetric and ratiometric fluorescent probe for cyanide sensing in aqueous media and live cells. , 2019, Journal of materials chemistry. B.

[12]  Zhixiang Han,et al.  Determination of Cyanide in Water and Food Samples Using an Efficient Naphthalene-Based Ratiometric Fluorescent Probe , 2019, ACS omega.

[13]  P. S. Chae,et al.  TURN-ON fluorescence detection of cyanide using an ensemble system consisting of a dansyl-based cationic probe and dicyanovinyl derivative , 2019, Dyes and Pigments.

[14]  Jianbin Chao,et al.  A novel near-infrared ratiometric fluorescent probe for cyanide and its bioimaging applications. , 2019, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[15]  K. Elango,et al.  An easy to make chemoreceptor for the selective ratiometric fluorescent detection of cyanide in aqueous solution and in food materials , 2019, New Journal of Chemistry.

[16]  T. Gunnlaugsson,et al.  Solution-State Anion Recognition, and Structural Studies, of a Series of Electron-Rich meta-Phenylene Bis(phenylurea) Receptors and Their Self-Assembled Structures. , 2018, The Journal of organic chemistry.

[17]  S. Vandarkuzhali,et al.  Phenothiazine Based Donor-Acceptor Compounds with Solid-State Emission in the Yellow to NIR Region and Their Highly Selective and Sensitive Detection of Cyanide Ion in ppb Level. , 2018, Chemistry.

[18]  You‐Ming Zhang,et al.  Rapid and Selective Detection of Cyanide Anion by Enhanced Fluorescent Emission and Colorimetric Color Changes at Micromole Levels in Aqueous Medium , 2018 .

[19]  Tianduo Li,et al.  Oligothiophene-based colorimetric and ratiometric fluorescence dual-channel cyanide chemosensor: Sensing ability, TD-DFT calculations and its application as an efficient solid state sensor. , 2018, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[20]  Maotian Xu,et al.  A highly selective and ratiometric fluorescent probe for cyanide by rationally altering the susceptible H-atom. , 2018, Talanta.

[21]  Ming Hui Chua,et al.  Triphenylethylenyl-based donor–acceptor–donor molecules: studies on structural and optical properties and AIE properties for cyanide detection , 2017 .

[22]  F. Zheng,et al.  A novel imidazophenazine-based metallogel act as reversible H2PO4− sensor and rewritable fluorescent display material , 2017 .

[23]  V. P. Muralidharan,et al.  Enantioselective recognition of unmodified amino acids by ligand-displacement assays with in situ generated 1:1 Cu(II)- BINOL imidazole complex , 2017 .

[24]  P. Molina,et al.  Anion Recognition Strategies Based on Combined Noncovalent Interactions. , 2017, Chemical reviews.

[25]  K. Thirumoorthy,et al.  Enantioselective fluorescent sensing of chiral carboxylic acid by engaging boronic acid and BINOL , 2017 .

[26]  Nakorn Niamnont,et al.  Turn-on fluorescent sensor for the detection of cyanide based on a novel dicyanovinyl phenylacetylene , 2017 .

[27]  T. Satoh,et al.  Polyacetylenes as Colorimetric and Fluorescent Chemosensor for Anions , 2017 .

[28]  A. Bende,et al.  Supramolecular anion recognition by β-HCH. , 2016, Chemical communications.

[29]  You‐Ming Zhang,et al.  A highly sensitive colorimetric chemodosimeter for cyanide anion by Michael addition based on a coumarin derivative , 2016 .

[30]  Juyoung Yoon,et al.  Fluorescent and Colorimetric Chemosensors for Anions, Metal Ions, Reactive Oxygen Species, Biothiols, and Gases , 2016 .

[31]  S. Velmathi,et al.  A fluorogenic and chromogenic dual sensor for the detection of cyanide and copper(II) in water samples and living cells , 2016 .

[32]  Jianbin Chao,et al.  Two high selective and sensitive ratiometric fluorescence probes for detecting hypochlorite , 2016 .

[33]  P. Beer,et al.  Halogen bonding anion recognition. , 2016, Chemical communications.

[34]  Sathiyanarayanan Kulathu Iyer,et al.  A chiral (S)-BINOL based fluorescent sensor for the recognition of Fe(III) and cascade discrimination of α-amino acids , 2016 .

[35]  Vijay Luxami,et al.  Benzimidazole based ratiometric chemosensor for detection of CN− and Cu2+ ions in protic/aqueous system: Elaboration as XOR logic operation , 2016 .

[36]  Yuanping Yi,et al.  Novel colorimetric and fluorescent off–on enantiomers with high selectivity for Fe3+ imaging in living cells , 2016 .

[37]  Yu Wang,et al.  A colorimetric and ratiometric fluorescent probe for the selective detection of cyanide anions in aqueous media and living cells , 2016 .

[38]  V. Srinivasadesikan,et al.  Acid/Base and H2PO4(-) Controllable High-Contrast Optical Molecular Switches with a Novel BODIPY Functionalized [2]Rotaxane. , 2015, ACS applied materials & interfaces.

[39]  P. Beer,et al.  Active‐Metal Template Synthesis of a Halogen‐Bonding Rotaxane for Anion Recognition , 2015, Chemistry.

[40]  Wei-Chi Lin,et al.  A ratiometric chemodosimeter for highly selective naked-eye and fluorogenic detection of cyanide. , 2015, Analytica chimica acta.

[41]  K. Velmurugan,et al.  Binol based “turn on” fluorescent chemosensor for mercury ion , 2015 .

[42]  Claudia Caltagirone,et al.  Applications of Supramolecular Anion Recognition. , 2015, Chemical reviews.

[43]  H. Ågren,et al.  Highly sensitive detection of low-level water content in organic solvents and cyanide in aqueous media using novel solvatochromic AIEE fluorophores , 2015 .

[44]  H. Ågren,et al.  A near-infrared “on–off” fluorescent and colourimetric cyanide chemodosimeter based on phenothiazine with applications in living cell imaging , 2014 .

[45]  Yixiang Cheng,et al.  (S)-Binaphthalene-based fluorescence polymer sensors for direct and visual F− detection , 2014 .

[46]  H. Tong,et al.  Dicyanovinyl-functionalized fluorescent hyperbranched conjugated polymer nanoparticles for sensitive naked-eye cyanide ion detection , 2014 .

[47]  Li Wang,et al.  Recent progress in the development of fluorometric and colorimetric chemosensors for detection of cyanide ions. , 2014, Chemical Society reviews.

[48]  Yi Li,et al.  Solvatochromic AIE luminogens as supersensitive water detectors in organic solvents and highly efficient cyanide chemosensors in water , 2014 .

[49]  Rajendra Kumar Konidena,et al.  Selective naked-eye cyanide detection in aqueous media using a carbazole-derived fluorescent dye , 2014 .

[50]  Wei-Chi Lin,et al.  Ratiometric fluorescent/colorimetric cyanide-selective sensor based on excited-state intramolecular charge transfer-excited-state intramolecular proton transfer switching. , 2014, Analytical chemistry.

[51]  Cally J E Haynes,et al.  Anion receptor chemistry: highlights from 2011 and 2012. , 2014, Chemical Society reviews.

[52]  J. Hua,et al.  Colorimetric and ratiometric near-infrared fluorescent cyanide chemodosimeter based on phenazine derivatives. , 2013, ACS applied materials & interfaces.

[53]  Cui‐Hua Zhao,et al.  An aggregation-induced emissive chromophore as a ratiometric fluorescent sensor for cyanide in aqueous media , 2013 .

[54]  T. J. Chow,et al.  Reaction-based colorimetric and ratiometric fluorescence sensor for detection of cyanide in aqueous media. , 2012, Chemistry, an Asian journal.

[55]  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.

[56]  J. Qin,et al.  New fluorescent and colorimetric probe for cyanide: direct reactivity, high selectivity, and bioimaging application. , 2012, ACS applied materials & interfaces.

[57]  L. Pu.  Enantioselective fluorescent sensors: a tale of BINOL. , 2012, Accounts of chemical research.

[58]  Ming Dong,et al.  A highly selective fluorescence-enhanced chemosensor for Al3+ in aqueous solution based on a hybrid ligand from BINOL scaffold and β-amino alcohol , 2012 .

[59]  Yixiang Cheng,et al.  Novel fluorescent sensor for Ag+ and Hg2+ based on the BINOL-pyrene derivative via click reaction , 2011 .

[60]  Juyoung Yoon,et al.  A near-infrared fluorescent sensor for detection of cyanide in aqueous solution and its application for bioimaging. , 2010, Chemical communications.

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

[62]  Jean-Marie Lehn,et al.  Comprehensive Supramolecular Chemistry , 1996 .