Synthesis, structural and spectroscopic properties of asymmetric Schiff bases derived from 2,3-diaminopyridine

Two Schiff base derivatives, 4-(2-amino-3-pyridyliminomethyl)phenol (I) and 3-(2-amino-3-pyridyliminomethyl)nitrobenzene (II), were synthesised and characterised by spectroscopy. The structure of I was determined by single crystal X-ray diffraction studies. The asymmetric Schiff base derived from 2,3-diaminopyridine selectively recognise transition and heavy metal cations, and some anion. Ligands I and II form stable complexes with Cu2+, Zn2+, Pb2+, Al3+ whereas ligand I also binds F~ ions. The stoichiometry for the host: cation is 1: 1 and 2: 1. The addition of F~ ion in CH3CN to ligand I causes a colour change of the solution from colourless to yellow. The binding behaviour of ligand I towards several ions was investigated using density functional theory calculations.

[1]  A. Vega,et al.  Experimental and theoretical studies of the ancillary ligand (E)-2-((3-amino-pyridin-4-ylimino)-methyl)-4,6-di-tert-butylphenol in the rhenium(I) core , 2015 .

[2]  A. A. A. Aziz,et al.  A novel highly sensitive and selective optical sensor based on a symmetric tetradentate Schiff-base embedded in PVC polymeric film for determination of Zn2+ ion in real samples , 2013 .

[3]  Keh-Feng Huang,et al.  A new selective colorimetric and fluorescent chemodosimeter for HSO4(-) based on hydrolysis of Schiff base. , 2013, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[4]  R. Santillán,et al.  A reversible fluorescent–colorimetric Schiff base sensor for Hg2+ ion , 2013 .

[5]  S. Velmathi,et al.  Synthesis and anion binding studies of azo-Schiff bases: Selective colorimetric fluoride and acetate ion sensors , 2013 .

[6]  A. Sreekanth,et al.  An efficient triazole-based fluorescent "turn-on" receptor for naked-eye recognition of F- and AcO-: UV-visible, fluorescence and 1H NMR studies. , 2013, Materials science & engineering. C, Materials for biological applications.

[7]  C. Wan,et al.  A Schiff-Based Colorimetric Fluorescent Sensor with the Potential for Detection of Fluoride Ions , 2013, Journal of Fluorescence.

[8]  M. Rezaeivala,et al.  A new asymmetric Schiff base system as fluorescent chemosensor for Al3 + ion , 2013 .

[9]  A. Abu‐Dief,et al.  Design, characterization, teratogenicity testing, antibacterial, antifungal and DNA interaction of few high spin Fe(II) Schiff base amino acid complexes. , 2013, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[10]  C. Dai,et al.  Structure of a new schiff base cobalt(III) complex with antibacterial activity , 2013, Journal of Structural Chemistry.

[11]  Parviz Norouzi,et al.  Comparative study of colorimetric sensors based on newly synthesized Schiff bases , 2013 .

[12]  Ruilong Sheng,et al.  Colorimetric and Highly Selective Fluorescence "Turn‐on" Detection of Cr3+ by Using a Simple Schiff Base Sensor , 2013 .

[13]  Serkan Erdemir,et al.  ‘Naked-eye’ detection of F− ions by two novel colorimetric receptors , 2013 .

[14]  P. Chattopadhyay,et al.  Cell permeable fluorescent receptor for detection of H2PO4(-) in aqueous solvent. , 2013, Organic & biomolecular chemistry.

[15]  Gholamhossein Grivani,et al.  Polymer-supported bis (2-hydroxyanyl) acetylacetonato molybdenyl Schiff base catalyst as effective, selective and highly reusable catalyst in epoxidation of alkenes , 2013 .

[16]  Ge Liu,et al.  Ratiometric fluorescence and colorimetric sensing of anion utilizing simple Schiff base derivatives , 2013, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[17]  J. Niu,et al.  Fe(3+)-selective fluorescent probe based on aminoantipyrine in aqueous solution. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[18]  Masoumeh Tabatabaee,et al.  Simultaneous trace-levels determination of Hg(II) and Pb(II) ions in various samples using a modified carbon paste electrode based on multi-walled carbon nanotubes and a new synthesized Schiff base. , 2012, Analytica chimica acta.

[19]  S. Velmathi,et al.  Colorimetric and fluorescent sensing of transition metal ions in aqueous medium by salicylaldimine based chemosensor. , 2012, Materials science & engineering. C, Materials for biological applications.

[20]  Chao-Yi Chiang,et al.  A new dual functional sensor: highly selective colorimetric chemosensor for Fe3+ and fluorescent sensor for Mg2+. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[21]  Junseong Lee,et al.  Synthesis, characterization of palladium hydroxysalen complex and its application in the coupling reaction of arylboronic acids: Mizoroki–Heck type reaction and decarboxylative couplings , 2012 .

[22]  Rehab M. Amin,et al.  Microplate assay for screening the antibacterial activity of Schiff bases derived from substituted benzopyran-4-one. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[23]  C. Amatore,et al.  Electrocatalytic oxidation of organic substrates with molecular oxygen using tetradentate ruthenium(III)-Schiff base complexes as catalysts , 2012 .

[24]  Zhengfeng Xie,et al.  Mn(OAc)2/Schiff base as a new efficient catalyst system for the Henry reaction of nitroalkanes with aldehydes , 2012 .

[25]  R. Yao,et al.  New Pb(II)-selective membrane electrode based on a new Schiff base complex , 2012 .

[26]  Jincai Wu,et al.  Ring opening polymerization of l-lactide by an electron-rich Schiff base zinc complex: An activity and kinetic study , 2012 .

[27]  Zhong-Ying Ma,et al.  Study on potential antitumor mechanism of a novel Schiff base copper(II) complex: synthesis, crystal structure, DNA binding, cytotoxicity and apoptosis induction activity. , 2011, Journal of inorganic biochemistry.

[28]  E. Doganci,et al.  Synthesis and characterization of two-armed poly(ɛ-caprolactone) polymers initiated by the Schiff's base complexes of copper(II) and nickel(II) , 2010 .

[29]  E. De Clercq,et al.  Synthesis, antiviral activity and cytotoxicity evaluation of Schiff bases of some 2-phenyl quinazoline-4(3)H-ones , 2010, European Journal of Medicinal Chemistry.

[30]  M. Yıldız,et al.  Synthesis, spectroscopic studies and crystal structure of (E)-2-(2,4-dihydroxybenzylidene)thiosemicarbazone and (E)-2-[(1H-indol-3-yl)methylene]thiosemicarbazone , 2009 .

[31]  Chang Ji,et al.  Catalytic reduction of 1- and 2-bromooctanes by a dinickel(I) Schiff base complex containing two salen units electrogenerated at carbon cathodes in dimethylformamide , 2008 .

[32]  Weilin Sun,et al.  Polymerization of isoprene catalyzed by neodymium heterocyclic Schiff base complex , 2008 .

[33]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[34]  E. Jacobsen,et al.  Highly Enantio- and Regioselective Quinone Diels—Alder Reactions Catalyzed by a Tridentate [(Schiff Base)CrIII] Complex. , 2006 .

[35]  Duncan M. Tooke,et al.  A Convenient Synthetic Route for the Preparation of Nonsymmetric Metallo- salphen Complexes , 2005 .

[36]  S. Jeon,et al.  A lead(II)-selective PVC membrane based on a Schiff base complex of N,N'-bis(salicylidene)-2,6-pyridinediamine. , 2005, Talanta.

[37]  B. Kamieński,et al.  Solid state 15N and 13C NMR study of dioxomolybdenum (VI) complexes of Schiff bases derived from trans-1,2-cyclohexanediamine , 2004 .

[38]  H. Wah,et al.  Synthesis, characterization and antibacterial properties of Schiff bases and Schiff base metal complexes derived from 2,3-diamino- pyridine , 1999 .

[39]  N. Galić,et al.  The Schiff bases of salicylaldehyde and aminopyridines as highly sensitive analytical reagents , 1997 .

[40]  Z. Cimerman,et al.  Structure and spectroscopic characteristics of Schiff bases of salicylaldehyde with 2,3-diaminopyridine , 1992 .

[41]  D. Waldeck.  Photoisomerization Dynamics of Stilbenes , 1991 .

[42]  P. Dubey,et al.  Formation of heterocyclic rings containing nitrogen: Part XXVI—Condensation of pyridine 2, 3-diamine with aromatic aldehydes , 1977 .

[43]  Hugo Schiff,et al.  Eine neue Reihe organischer Diamine , 1866 .