Solvatochromism, spectral properties and antimicrobial activities of new azo–azomethine dyes with N2S2O2 donor set of atoms

Abstract Six new azo–azomethine dyes, H 2 L n ( n  = 1–6), with N 2 S 2 O 2 donor set of atoms have been prepared via condensation reaction of 1,10-diaza-4,7-dithiadecane, I , with substituted azo-coupled salicylaldehyde. The dyes were characterized by IR, UV–Vis and 1 H NMR spectroscopic methods as well as elemental analysis. The solvatochromic behavior of the dyes was also probed by studying their UV–Vis spectra in four pure organic solvents of different polarities and a meaningful correlation was observed. Furthermore, all prepared dyes were assayed for their antibacterial and antifungal activities by disc diffusion method. The results indicated that all prepared dyes show good inhibition against Staphylococcus epidermidis and Bacillus cereus and did not show any antibacterial activity against Escherichia coli as compared to standard drugs.

[1]  H. Khanmohammadi,et al.  Thermally stable water insoluble azo-azomethine dyes: synthesis, characterization and solvatochromic properties. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[2]  A. M. Khedr,et al.  Synthesis and spectral studies of 5-[3-(1,2,4-triazolyl-azo]-2,4-dihydroxybenzaldehyde (TA) and its Schiff bases with 1,3-diaminopropane (TAAP) and 1,6-diaminohexane (TAAH). Their analytical application for spectrophotometric microdetermination of cobalt(II). Application in some radiochemical studie , 2005 .

[3]  A. El‐Bindary,et al.  Structural and characterization of novel copper(II) azodye complexes. , 2011, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[4]  S. El-Daly,et al.  UV/Vis, IR and 1H NMR spectroscopic studies of bisazo-dianil compounds based on 5-(2-carboxyphenyl azo)-salicylaldehyde and primary diamines. , 2003, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[5]  M. M. Abd El Aziz,et al.  Mono and binuclear Ag(I), Cu(II), Zn(II) and Hg(II) complexes of a new azo-azomethine as ligand: synthesis, potentiometric, spectral and thermal studies. , 2011, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[6]  M. Baik,et al.  Torsionally responsive C3-symmetric azo dyes: azo-hydrazone tautomerism, conformational switching, and application for chemical sensing. , 2010, Journal of the American Chemical Society.

[7]  Z. Rezvani,et al.  The synthesis, characterization, thermal and optical properties of copper, nickel, and vanadyl complexes derived from azo dyes , 2009 .

[8]  E. Ispir The synthesis, characterization, electrochemical character, catalytic and antimicrobial activity of novel, azo-containing Schiff bases and their metal complexes , 2009 .

[9]  Abedin Zabardasti,et al.  Synthesis and characterization of an azo dibenzoic acid Schiff base and its Ni(II), Pb(II), Zn(II) and Cd(II) complexes. , 2013, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[10]  L. Açık,et al.  Antimicrobial properties and DNA interactions studies of 3-hetarylazoquinoline-2,4-diol compounds , 2012, Turkish Journal of Chemistry.

[11]  S. Dadfarnia,et al.  Immobilized salen (N,N′-bis (salicylidene) ethylenediamine) as a complexing agent for on-line sorbent extraction/preconcentration and flow injection–flame atomic absorption spectrometry , 2005 .

[12]  Light-scattering determination of visco-elastic and electro-optic parameters of azo and anthraquinone dye-doped liquid crystal molecules and consistent neural network empirical physical formula construction for scattering intensities , 2011 .

[13]  Samir Alghool,et al.  Synthesis, spectroscopic thermal and biological activity studies on azo-containing Schiff base dye and its Cobalt(II), Chromium(III) and Strontium(II) complexes , 2010 .

[14]  M. Kurt,et al.  Synthesis, structure characterization and antimicrobial evaluation of 4-(substituted phenylazo)-3,5-diacetamido-1H-pyrazoles. , 2013, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[15]  V. McKee,et al.  Synthesis, characterization and antimicrobial studies of 2-{(E)-[(2-hydroxy-5-methylphenyl)imino]methyl}-4-[(E)-phenyldiazenyl]phenol as a novel azo-azomethine dye , 2013 .

[16]  K. El-Baradie,et al.  Cu(II) complexes of monobasic bi- or tridentate (NO, NNO) azo dye ligands: Synthesis, characterization, and interaction with Cu-nanoparticles , 2013 .

[17]  K. M. Rathod,et al.  Synthesis and Antimicrobial Activity of Azo Compounds Containing m-Cresol Moiety , 2012 .

[18]  H. Khanmohammadi,et al.  Azo-azomethine dyes with N, O, S donor set of atoms and their Ni(II) complexes: Synthesis, characterization and spectral properties , 2013 .

[19]  A. Fonseca,et al.  Enhancement of the photochromic switching speed of bithiophene azo dyes , 2012 .

[20]  M. Refat,et al.  Synthesis and spectroscopic studies of some transition metal complexes of a novel Schiff base ligands derived from 5-phenylazo-salicyladehyde and o-amino benzoic acid. , 2006, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[21]  A. M. Sousa,et al.  Thienylpyrrole azo dyes : Synthesis, solvatochromic and electrochemical properties , 2005 .

[22]  H. Khanmohammadi,et al.  Solvatochromic and electrochemical properties of new thermally stable azo–azomethine dyes with N2S2O2 donor set of atoms , 2013 .

[23]  C. J. Tredwell,et al.  Picosecond time resolved fluorescence lifetimes of the polymethine and related dyes , 1979 .

[24]  G. Socrates,et al.  Infrared and Raman characteristic group frequencies : tables and charts , 2001 .

[25]  H. A. Weber,et al.  Development of a Scaleable Synthesis for 1,2-Bis(2-aminophenylthio)ethane (APO-Link) Used in the Production of Bismaleimide Resin , 2007 .

[26]  M. A. Rauf,et al.  Studies on solvatochromic behavior of dyes using spectral techniques , 2013 .

[27]  Z. Rezvani,et al.  Syntheses and mesomorphic properties of new oxygen-bridged dicopper complex homologous derived from azo-containing salicylaldimine Schiff base ligands , 2009 .

[28]  A. Gilani,et al.  Solvatochromism and dichroism of fluorinated azoquinolin-8-ol dyes in liquid and liquid crystalline solutions , 2008 .

[29]  R. Mohareb,et al.  Design and Synthesis of Novel Antimicrobial Acyclic and Heterocyclic Dyes and Their Precursors for Dyeing and/or Textile Finishing Based on 2-N-Acylamino-4,5,6,7-tetrahydro-benzo[b]thiophene Systems , 2011, Molecules.

[30]  S. Amani,et al.  Synthesis, Spectroscopy, Thermal Analysis, Magnetic Properties and Biological Activity Studies of Cu(II) and Co(II) Complexes with Schiff Base Dye Ligands , 2012, Molecules.

[31]  Sh. Golghasemi Sorkhabi,et al.  Substituent and solvent effects on the spectroscopic properties and dipole moments of hydroxyl benzaldehyde azo dye and related Schiff bases , 2013 .

[32]  S. Icli,et al.  New thiophene-based azo ligands containing azo methine group in the main chain for the determination of copper(II) ions , 2007 .

[33]  C. Reichardt Solvents and Solvent Effects in Organic Chemistry , 1988 .

[34]  M. Olmstead,et al.  Synthesis, Crystal Structure, Spectroscopic, Electrochemical and Antimicrobial Properties of Cu(II) Complex with the Mixed Ligands of 2,9-Dimethyl-1,10-phenanthroline and 4-Hydroxypyridine-2,6-dicarboxylic Acid , 2010 .

[35]  D. Ray,et al.  Sulfur-ligated nickel oxidation states. Chemistry of a family of NizS2N4 (z = +2, +3, +4) complexes incorporating hexadentate thioether-imine-oxime binding , 1991 .