Colorimetric sensing of cyanide and fluoride ions by diaminomalenonitrile based Schiff bases

Abstract Two new diaminomalenonitrile (DMN) based Schiff bases have been synthesized and explored as a highly efficient receptor for fluoride and cyanide anions. Detection of anions induced by deprotonation of –NH 2 followed by transfer of proton to the electron deficient nitrogen atom of –CN which induce the strong charge transfer (CT). Anion selectivity was controlled by the fluorophore attached to the DMN, the fluorophore can tune the electron push–pull property. This phenomenon was confirmed by 1 H NMR and DFT calculations.

[1]  A. Hamilton,et al.  A Dual Channel Fluorescence Chemosensor for Anions Involving Intermolecular Excited State Proton Transfer. , 2001, Angewandte Chemie.

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

[3]  Philip A. Gale,et al.  Anion Receptor Chemistry , 2006 .

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

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

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

[7]  M. Licchelli,et al.  What anions do to N-H-containing receptors. , 2006, Accounts of chemical research.

[8]  J. Sankar,et al.  Exclusive fluoride ion recognition and fluorescence "turn-on" response with a label-free DMN Schiff base. , 2013, The Analyst.

[9]  J. Bats,et al.  Rapid and highly sensitive dual-channel detection of cyanide by bis-heteroleptic ruthenium(II) complexes. , 2012, Inorganic chemistry.

[10]  T. Gunnlaugsson,et al.  Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors , 2006 .

[11]  S. Bhosale,et al.  A core-substituted naphthalene diimide fluoride sensor. , 2009, Organic letters.

[12]  Jonathan L. Sessler,et al.  Naked-Eye Detection of Anions in Dichloromethane: Colorimetric Anion Sensors Based on Calix[4]pyrrole , 2000 .

[13]  C. Tung,et al.  A colorimetric and fluorometric dual-modal chemosensor for cyanide in water , 2012 .

[14]  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.

[15]  S. Langford,et al.  A chemodosimer based on a core-substituted naphthalene diimide for fluoride ion detection , 2011 .

[16]  J. Sankar,et al.  A selective fluoride sensor and a digital processor with "Write-Read-Erase-Read" behaviour. , 2014, Dalton transactions.

[17]  P. Beer.  Transition-Metal Receptor Systems for the Selective Recognition and Sensing of Anionic Guest Species , 1998 .

[18]  Thawatchai Tuntulani,et al.  Chromogenic anion sensors. , 2003, Chemical Society reviews.

[19]  S. Saha,et al.  Fluoride ion sensing by an anion-π interaction. , 2010, Journal of the American Chemical Society.

[20]  Philip A. Gale.  Anion and ion-pair receptor chemistry: highlights from 2000 and 2001 , 2003 .

[21]  R. K. Kanaparthi,et al.  Ratiometric fluorescence signalling of fluoride ions by an amidophthalimide derivative , 2007 .

[22]  T. Gunnlaugsson,et al.  Colorimetric sensing of anions in aqueous solution using a charge neutral, cleft-like, amidothiourea receptor: tilting the balance between hydrogen bonding and deprotonation in anion recognition. , 2008, Organic & biomolecular chemistry.

[23]  I. R. Morgan,et al.  Evaluation of electronics, electrostatics and hydrogen bond cooperativity in the binding of cyanide and fluoride by Lewis acidic ferrocenylboranes. , 2010, Inorganic chemistry.

[24]  Keli Han,et al.  Colorimetric and ratiometric fluorescence sensing of fluoride: tuning selectivity in proton transfer. , 2005, The Journal of organic chemistry.