Fluorogenic and chromogenic heterocyclic thiourea: Selective recognition of cyanide ion via nucleophilic addition reaction and real sample analysis

Earthquake Spectra - Tập 221 - Trang 1104-1113 - 2015
Sivalingam Suganya1, Sivan Velmathi1
1Organic and Polymer Synthesis Laboratory, Department of Chemistry, National Institute of Technology, Tiruchirappalli 620015, India

Tài liệu tham khảo

Suksai, 2003, Chromogenic anion sensors, Chem. Soc. Rev., 32, 192, 10.1039/b209598j Martınez-Manez, 2006, Chemodosimeters and 3D inorganic functionalised hosts for the fluoro-chromogenic sensing of anions, Coord. Chem. Rev., 250, 3081, 10.1016/j.ccr.2006.04.016 Gale, 2008, Anion receptors based on organic frameworks: highlights from 2005 and 2006, Chem. Soc. Rev., 37, 151, 10.1039/B715825D Sun, 2009, A novel fluorescent and chromogenic probe for cyanide detection in water based on the nucleophilic addition of cyanide to imine group, Talanta, 80, 996, 10.1016/j.talanta.2009.08.026 Zhang, 2013, A naphtholic Schiff base for highly selective sensing of cyanide via different channels in aqueous solution, Dyes Pigments, 99, 857, 10.1016/j.dyepig.2013.07.015 Sun, 2009, Fluorescent and chromogenic probes bearing salicylaldehyde hydrazone functionality for cyanide detection in aqueous solution, Sens. Actuators B, 143, 171, 10.1016/j.snb.2009.09.038 Udhayakumari, 2015, Novel chemosensor for multiple target anions: the detection of F− and CN− ion via different approach, J. Fluorine Chem., 175, 180, 10.1016/j.jfluchem.2015.04.014 Tsui, 2012, Azo dyes featuring with nitrobenzoxadiazole (NBD) unit: a new selective chromogenic and fluorogenic sensor for cyanide ion, Sens. Actuators B, 161, 510, 10.1016/j.snb.2011.10.069 Yang, 2006, Acridinium salt based fluorescent and colorimetric chemosensor for the detection of cyanide in water, Org. Lett., 8, 5721, 10.1021/ol062323r Xu, 2010, Sensors for the optical detection of cyanide ion, Chem. Soc. Rev., 39, 127, 10.1039/B907368J Tomasulo, 2006, Chromogenic oxazines for cyanide detection, J. Org. Chem., 71, 744, 10.1021/jo052096r Ros-Lis, 2002, A selective chromogenic reagent for cyanide determination, Chem. Commun., 2248, 10.1039/B206500B García, 2005, Pyrylium-containing polymers as sensory materials for the colorimetric sensing of cyanide in water, Chem. Commun., 2790, 10.1039/b502374b Tomasulo, 2005, Colorimetric detection of cyanide with a chromogenic oxazine, Org. Lett., 7, 4633, 10.1021/ol051750m Kumar, 2010, Thiourea based novel chromogenic sensor for selective detection of fluoride and cyanide anions in organic and aqueous media, Anal. Chim. Acta, 663, 77, 10.1016/j.aca.2010.01.025 Li, 2010, Anion complexation and sensing using modified urea and thiourea-based receptors, Chem. Soc. Rev., 39, 3729, 10.1039/b926160p Shao, 2008, A simple and efficient colorimetric anion sensor based on a thiourea group in DMSO and DMSO – water and its real-life application, Talanta, 75, 1015, 10.1016/j.talanta.2007.12.041 Wu, 2006, A unique NH-spacer for N-benzamidothiourea based anion sensors. Substituent effect on anion sensing of the ICT dual fluorescent N-(p-dimethylaminobenzamido)-N′-arylthioureas, Org. Biomol. Chem., 4, 624, 10.1039/b513969d Lee, 2001, An azophenol-based chromogenic anion sensor, Org. Lett., 3, 5, 10.1021/ol006690t Vinithra, 2013, Naked eye sensing of anions using thiourea based chemosensors with real time application, Tetrahedron Lett., 54, 5612, 10.1016/j.tetlet.2013.08.005 Bhardwaj, 2011, New tripodal and dipodal colorimetric sensors for anions based on tris/bis-urea/thiourea moieties, Supramol. Chem., 23, 790, 10.1080/10610278.2011.593629 Miyaji, 2000, Naked-eye detection of anions in dichloromethane: colorimetric anion sensors based on Calix[4]pyrrole, Angew. Chem. Int. Ed., 39, 1777, 10.1002/(SICI)1521-3773(20000515)39:10<1777::AID-ANIE1777>3.0.CO;2-E Miyaji, 2001, Off-the-shelf colorimetric anion sensors, Angew. Chem. Int. Ed., 40, 154, 10.1002/1521-3773(20010105)40:1<154::AID-ANIE154>3.0.CO;2-G Jimenez, 2002, Selective fluoride sensing using colorimetric reagents containing anthraquinone and urea or thiourea binding sites, Tetrahedron Lett., 43, 2823, 10.1016/S0040-4039(02)00363-5 Cho, 2006, Naked eye fluoride ion chemosensors with anthraquinone derivatives, Bull. Korean Chem. Soc., 27, 1967, 10.5012/bkcs.2006.27.12.1967 Lee, 2004, Efficient fluoride-selective fluorescent host: experiment and theory, J. Org. Chem., 69, 943, 10.1021/jo0356457 Kim, 2002, A new fluorescent PET chemosensor for fluoride ions, Chem. Commun., 770, 10.1039/b110139k Jose, 2004, Efficient and simple colorimetric fluoride ion sensor based on receptors having urea and thiourea binding sites, Org. Lett., 6, 3445, 10.1021/ol048829w Satheshkumar, 2013, Spectral and DFT studies on simple and selective colorimetric sensing of fluoride ions via enhanced charge transfer using a novel signalling unit, Dyes Pigments, 96, 364, 10.1016/j.dyepig.2012.08.014 Chauhan, 2008, Anion sensing by phenazine-based urea/thiourea receptors, Tetrahedron Lett., 49, 6646, 10.1016/j.tetlet.2008.09.033 Kumari, 2011, Colorimetric probes based on anthraimidazolediones for selective sensing of fluoride and cyanide ion via intramolecular charge transfer, J. Org. Chem., 76, 8215, 10.1021/jo201290a Niu, 2008, A simple yet highly selective colorimetric sensor for cyanide anion in an aqueous environment, Org. Biomol. Chem., 6, 3038, 10.1039/b808589g Djazuli, 1999, Cyanogen content of cassava roots and flour in Indonesia, Food Chem., 65, 523, 10.1016/S0308-8146(98)00218-0 Burns, 2012, Total cyanide content of cassava food products in Australia, J. Food Compos. Anal., 25, 79, 10.1016/j.jfca.2011.06.005 Egan, 1998, Simple picrate paper kit for determination of the cyanogenic potential of cassava flour, J. Sci. Food Agric., 76, 39, 10.1002/(SICI)1097-0010(199801)76:1<39::AID-JSFA947>3.0.CO;2-M Saha, 2010, Specific recognition and sensing of CN− in sodium cyanide solution, Org. Lett., 12, 3406, 10.1021/ol101281x Hamza, 2010, Anal. Chim. Acta, 657, 69, 10.1016/j.aca.2009.10.025 Abbaspour, 2002, Dual-wavelength beta-correction spectrophotometry for selective determination of Zr, Talanta, 57, 807, 10.1016/S0039-9140(02)00067-X Gao, 1994, Determination of antimony in waste water with chromazurols by beta-correction spectrophotometry, Analyst, 119, 2109, 10.1039/an9941902109 Chen, 2006, Dipyrrole carboxamide derived selective ratiometric probes for cyanide ion, Org. Lett., 8, 5053, 10.1021/ol061969g Nandi, 2014, Optical chemosensor for the detection of cyanide in water based on ethyl(hydroxyethyl)cellulose functionalized with Brooker's merocyanine, Anal. Chem., 86, 4653, 10.1021/ac501233x Sondhi, 2011, Conventional and microwave-assisted synthesis of imidazole and guanidine derivatives and their biological evaluation, Med. Chem. Res., 20, 887, 10.1007/s00044-010-9410-6 Ren, 2008, A highly sensitive and selective chemosensor for cyanide, Talanta, 75, 760, 10.1016/j.talanta.2007.12.024 Zhang, 2008, A near-infrared croconium dye-based colorimetric chemodosimeter for biological thiols and cyanide anion, Sens. Actuators B, 129, 152, 10.1016/j.snb.2007.07.094 Shiraishi, 2011, Rapid colorimetric sensing of cyanide anion in aqueous media with a spiropyran derivative containing a dinitrophenolate moiety, Tetrahedron Lett., 52, 1515, 10.1016/j.tetlet.2011.01.110 Cho, 2008, The benzil–cyanide reaction and its application to the development of a selective cyanide anion indicator, J. Am. Chem. Soc, 130, 12163, 10.1021/ja8039025 Sun, 2009, Colorimetric detection of cyanide with N-nitrophenyl benzamide derivatives, Tetrahedron, 65, 3480, 10.1016/j.tet.2009.02.023 Liu, 2011, Iridium(III) complex-coated nanosystem for ratiometric upconversion luminescence bioimaging of cyanide anions, J. Am. Chem. Soc., 133, 15276, 10.1021/ja205907y You, 2014, A single chemosensor for multiple target anions: the simultaneous detection of CN– and OAc– in aqueous media, Sens. Actuators B, 202, 645, 10.1016/j.snb.2014.05.124 Croisé, 2009, A straightforward method for the colorimetric detection of endogenous biological cyanide, Anal. Chem., 81, 9493, 10.1021/ac901977u Dong, 2011, A selective, sensitive, and chromogenic chemodosimeter for cyanide based on the 1,1′-binaphthyl Scaffold, J. Org. Chem., 76, 6962, 10.1021/jo201269e Chung, 2006, N-Acyl triazenes as tunable and selective chemodosimeters toward cyanide ion, J. Org. Chem., 71, 9470, 10.1021/jo061798t Niu, 2008, A highly selective and synthetically facile aqueous-phase cyanide probe, Tetrahedron Lett., 49, 6521, 10.1016/j.tetlet.2008.08.115 Yang, 2014, Red turn-on fluorescent phenazine-cyanine chemodosimeters for cyanide anion in aqueous solution and its application for cell imaging, Sens. Actuators B, 203, 833, 10.1016/j.snb.2014.07.045 Gupta, 2014, Colorimetric sensor for cyanide and acetate ion using novel biologically active hydrazones, Sens. Actuators B, 204, 125, 10.1016/j.snb.2014.07.029 Sun, 2013, A ratiometric fluorescent probe based on benzo [e] indolium for cyanide ion in water, Sens. Actuators B, 185, 638, 10.1016/j.snb.2013.05.049 Na, 2013, Colorimetric and fluorometric probe for the highly selective and sensitive detection of cyanide based on coumarinyloxime, Sens. Actuators B, 188, 1043, 10.1016/j.snb.2013.07.098 Lee, 2014, A new bis-pyrene derivative as a selective colorimetric and fluorescent chemosensor for cyanide and fluoride and anion-activated CO2 sensing, Sens. Actuators B, 199, 369, 10.1016/j.snb.2014.04.005 Shan, 2014, Nitro substituted chalcone derivatives as quick-response chemosensors for cyanide anions, Sens. Actuators B, 198, 15, 10.1016/j.snb.2014.02.100 Yang, 2014, A new highly selective and turn-on fluorescence probe for detection of cyanide, Sens. Actuators B, 193, 220, 10.1016/j.snb.2013.11.094 Zhou, 2014, A new colorimetric and fluorescent chemodosimeter for fast detection of cyanide, Sens. Actuators B, 203, 382, 10.1016/j.snb.2014.07.002 Peng, 2013, A highly selective ratiometric and colorimetric chemosensor for cyanide detection, Dyes Pigments, 98, 327, 10.1016/j.dyepig.2013.03.024 Ariga, 2014, Layer-by-layer nanoarchitectonics: invention, innovation, and evolution, Chem. Lett., 43, 36, 10.1246/cl.130987 Hu, 2014, Luminescent metal–organic frameworks for chemical sensing and explosive detection, Chem. Soc. Rev., 43, 5815, 10.1039/C4CS00010B