Mechanosynthesis of Diaminobiphenyls-Based Schiff’s Bases as Simple Probes for the Naked-Eye Detection of Cyanide Ion

Cyanide ions are known to be lethal for insects and mammals and harmful for the environment, and new methods for their selective detection are in high demand. Herein, the mechanosynthesis of simple Schiff’s bases-based probes S1–S3 for visual detection of CN− anion is reported. These probes were obtained by means of a reaction between isomeric 4,4-, 3,3- and 2,2-diaminobiphenyls and 4-nitrobenzaldehyde under ball milling conditions. The probes showed high selectivity and sensitivity toward CN− anion via a dramatic “yellow-to-dark purple” color change with a detection limit of 26 × 103, 8.7 × 103 and 14 × 103 ppm for S1–S3, respectively. The proposed mechanism of the detection suggests the deprotonation of a proton from an imine moiety, followed by the formation of charge transfer complexes (CTC).

[1]  R. Shanmugapriya,et al.  A multi-site probe for selective detection of cyanide and sulphite ions via different mechanisms with concomitant different fluorescent behaviors , 2022, Results in Chemistry.

[2]  M. S. Akhter,et al.  Naked Eye Chemosensing of Anions by Schiff Bases , 2020, Critical reviews in analytical chemistry.

[3]  Bahaaudin M. Raffah,et al.  New two rings Schiff base liquid crystals; ball mill synthesis, mesomorphic, Hammett and DFT studies , 2020 .

[4]  S. Dey,et al.  Chromogenic hydrazide Schiff base reagent: Spectrophotometric determination of CN- ion. , 2020, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[5]  H. Khanmohammadi,et al.  A new azo-azomethine sensor for detection of CN- and AcO- anions: Highly selective chemosensor for naked eye detection of sodium diclofenac. , 2019, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[6]  B. Narayana,et al.  Aromatic aldehyde based chemosensors for fluoride and cyanide detection in organic and aqueous media: Ascertained by characterization, spectroscopic and DFT studies , 2019, Inorganica Chimica Acta.

[7]  M. Amirnasr,et al.  A new fluorene derived Schiff-base as a dual selective fluorescent probe for Cu2+ and CN. , 2019, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[8]  M. Yıldız,et al.  A Schiff Base Sensor Selective to Anions, Biological Activity and Spectral Studies , 2018, Journal of the Turkish Chemical Society, Section A: Chemistry.

[9]  Kentaro Nakamura,et al.  Synthesis of Aryl Iodides from Arylhydrazines and Iodine , 2018, ACS omega.

[10]  Yousef M. Hijji,et al.  Substituted 2-Aminobenzothiazoles Salicylidenes Synthesis and Characterization as Cyanide Sensors in Aqueous Medium , 2018, Sensors.

[11]  C. Yin,et al.  A NIR, special recognition on HS−/CN− colorimetric and fluorescent imaging material for endogenous H2S based on nucleophilic addition , 2017 .

[12]  J. Namieśnik,et al.  Cyanides in the environment—analysis—problems and challenges , 2017, Environmental Science and Pollution Research.

[13]  Asmaa Aboelnaga,et al.  Ball Milling Assisted Solvent and Catalyst Free Synthesis of Benzimidazoles and Their Derivatives , 2016, Molecules.

[14]  S. Amani,et al.  Iconography : Naked-eye detection of cyanide ions in aqueous media based on an azo-azomethine chemosensor , 2016 .

[15]  P. Kienesberger,et al.  New Atglistatin closely related analogues: Synthesis and structure-activity relationship towards adipose triglyceride lipase inhibition. , 2016, European journal of medicinal chemistry.

[16]  Kadir Aslan,et al.  A Highly Selective Sensor for Cyanide in Organic Media and on Solid Surfaces , 2016, Sensors.

[17]  J. Jurczak,et al.  Recognizing the Limited Applicability of Job Plots in Studying Host-Guest Interactions in Supramolecular Chemistry. , 2016, The Journal of organic chemistry.

[18]  W. Shi,et al.  A new highly selective fluorescent turn-on chemosensor for cyanide anion. , 2015, Talanta.

[19]  Hongda Li,et al.  Colorimetric and fluorometric dual-modal probes for cyanide detection based on the doubly activated Michael acceptor and their bioimaging applications. , 2014, Analytica chimica acta.

[20]  Juyoung Yoon,et al.  A new bis-pyrene derivative as a selective colorimetric and fluorescent chemosensor for cyanide and fluoride and anion-activated CO2 sensing , 2014 .

[21]  H. Eshghi,et al.  Synthesis of novel bis(β-aminocarbonyl) compounds and some β-aminocarbonyls by catalyst-free multicomponent Mannich reactions , 2014, Journal of the Iranian Chemical Society.

[22]  S. Bhattacharya,et al.  An efficient probe for rapid detection of cyanide in water at parts per billion levels and naked-eye detection of endogenous cyanide. , 2014, Chemistry, an Asian journal.

[23]  Sha Long,et al.  Schiff Bases: A Short Survey on an Evergreen Chemistry Tool , 2013, Molecules.

[24]  P. Bühlmann,et al.  Getting more out of a Job plot: determination of reactant to product stoichiometry in cases of displacement reactions and n:n complex formation. , 2011, The Journal of organic chemistry.

[25]  Jian Xu,et al.  Novel indole based colorimetric and "turn on" fluorescent sensors for biologically important fluoride anion sensing. , 2011, Journal of photochemistry and photobiology. B, Biology.

[26]  P. Dasgupta,et al.  Recent developments in cyanide detection: a review. , 2010, Analytica chimica acta.

[27]  Juyoung Yoon,et al.  A highly selective cyanide sensing in water via fluorescence change and its application to in vivo imaging. , 2009, Chemical communications.

[28]  Rajesh Roshan Dash,et al.  Cyanide in industrial wastewaters and its removal: a review on biotreatment. , 2009, Journal of hazardous materials.

[29]  Liqiang Wang,et al.  Preparation of unsymmetrical biaryls by Pd(II)-catalyzed cross-coupling of aryl iodides. , 2009, Organic letters.

[30]  Xueliang Jiang,et al.  A simple yet highly selective colorimetric sensor for cyanide anion in an aqueous environment. , 2008, Organic & biomolecular chemistry.

[31]  J. Sessler,et al.  The benzil rearrangement reaction: trapping of a hitherto minor product and its application to the development of a selective cyanide anion indicator. , 2008, Organic letters.

[32]  Mujahid Hussain Bukhari,et al.  Synthesis, spectroscopic and cytotoxic studies of biologically active new schiff bases derived from p-nitrobenzaldehyde. , 2007, Chemical & pharmaceutical bulletin.

[33]  G. Surpateanu,et al.  Development of a competitive continuous variation plot for the determination of inclusion compounds stoichiometry , 2007 .

[34]  J. Tae,et al.  Acridinium salt based fluorescent and colorimetric chemosensor for the detection of cyanide in water. , 2006, Organic letters.

[35]  Ian Stewart,et al.  Recreational and occupational field exposure to freshwater cyanobacteria – a review of anecdotal and case reports, epidemiological studies and the challenges for epidemiologic assessment , 2006, Environmental health : a global access science source.

[36]  C. D. Geddes,et al.  Cyanide-sensitive fluorescent probes. , 2005, Dyes and pigments : an international journal.

[37]  V. Gil,et al.  On the use of the method of continuous variations , 1990 .

[38]  K. Ingham.  On the application of Job's method of continuous variation to the stoichiometry of protein-ligand complexes. , 1975, Analytical biochemistry.

[39]  Alankar Shrivastava,et al.  Methods for the determination of limit of detection and limit of quantitation of the analytical methods , 2011 .

[40]  Juyoung Yoon,et al.  Sensors for the optical detection of cyanide ion. , 2010, Chemical Society reviews.

[41]  J. Vetter.  Plant cyanogenic glycosides. , 2000, Toxicon : official journal of the International Society on Toxinology.

[42]  H. Schiff.  Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen , 1864 .