All Title Author
Keywords Abstract

Green Synthesis of New Tetra Schiff Bases and Bis-Azo Bis-Schiff Bases Derived from 2,6-Diaminopyridine as Promising Photosensitizers

DOI: 10.4236/ijoc.2018.83023, PP. 309-318

Keywords: Schiff Base, Azo-Schiff Base, 2,6-Diaminopyridine, Azo-Salicyladehyde, Photosensitizer

Full-Text   Cite this paper   Add to My Lib


Nine new tetra Schiff bases (M2 - M9) were prepared in moderate yields via the condensation of different aromatic amines and bis-Schiff base (M1) in microwave synthesizer. Also five new azo-Schiff bases (M16 - M20) were prepared by the condensation of (M1) with the azo-salicylaldehyde (M11 - M15) using the same method. The green synthesis by microwave irradiation was chosen as route due to its novelty, cleanliness, efficiency, time and solvent saving properties compared with the conventional methods which lack these advantages; such as time consume and wasting environment polluting organic solvents to achieve the same efficiency in synthesis. The prepared compounds which are believed by us to be competent as photosensitizers in photochemical systems were identified by IR and NMR spectroscopy besides elemental analysis.


[1]  Bringmann, G., Dreyer, M., Faber, J.H., Dalsgaard, P.W. and Jaroszewski, J.W. (2004) Ancistrotanzanine C and Related 5,1’- and 7,3’-Coupled Naphthylisoquinoline Alkaloids from Ancistrocladus Tanzaniensis. Journal of Natural Product, 67, 743-748.
[2]  Salimon, J., Salih, N., Ibrahim, H. and Yousif, E. (2010) Synthesis of 2-N-Salicylidene-5-(substituted)-1,3,4-thiadiazole as Potential Antimicrobial Agents. Asian Journal of Chemistry, 22, 5289-5296.
[3]  Guo, Z., Xing, R., Liu, S., Zhong, Z., Ji, X. and Wang, L. (2007) Antifungal Properties of Schiff Bases of Chitosan, N-Substituted Chitosan and Quanternized Chitosan. Carbohydrate Research, 342, 1329-1332.
[4]  Hania, M.M. (2009) Synthesis of Some Imines and Investigation of Their Biological Activity. E-Journal of Chemistry, 6, 629-637.
[5]  Tapabashi, N.O. (2016) Schiff Bases as Corrosion Inhibitors for Carbon Steel in HCl Solution. International Journal of Engineering and Advanced Research Technology, 2, 1-3.
[6]  Mohammed, H.A. and Taha, N.I. (2017) Microwave Preparation and Spectroscopic Investigation of Binuclear Schiff Base Metal Complexes Derived from 2,6-Diaminopyridine with Salicylaldehyde. International Journal of Organic Chemistry, 7, 412-419.
[7]  Tümer, M., Ekinci, D. and Tümer, F.A. (2007) Synthesis, Chracterization and Properties of Some Divalent Metal (II) Complexes: Their Electrochemical, Catalytic, Thermal and Antimicrobial Activity Studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 67, 916-921.
[8]  Mahmoud, M.J., Numan, A.T. and Al-Obaidi, O.B.M.S. (2013) Synthetic and Characterization of New Schiff Bases Complexes with CoII, NiII, CuII and PdII Ions. Journal of Al-Nahrain University, 16, 28-36.
[9]  Nayak, S., Gamez, P., Kozlevc’ar, B., Pevec, A., Roubeau, O., Dehnen, S. and Reedijik, J. (2011) Coordination Compounds from the Planar Tridentate Schiff-Base Ligand 2-Methoxy-6-((quinolin-8-ylimino)methyl)phenol (mqmpH) with Several Transition Metal Ions: Use of [Fe III(mqmp)(CH3OH)Cl2] in the Catalytic Oxidation of Alkanes and Alkanes. Polyhedron, 29, 2291-2296.
[10]  Kailas, H.K., Sheetal, P.J., Anita, P. and Apoorva, H. (2016) Four Synthesis Methods of Schiff Base Ligands and Preparation of their Metal Complex with IR and Antimicrobial Investigation. World Journal of Pharmacy and Pharmaceutical Sciences, 5, 1055-1063.
[11]  Mirza-Aghayan, M., Ghassemzadeh, M., Hoseini, M. and Boloutchian, M. (2006) Microwave-Assisted Synthesis of the Tetradentate Schiff-Bases under Solvent-Free and Catalyst-Free Condition. Synthetic Communications, 33, 521-523.
[12]  Kulshrestha, A. and Baluja, S. (2010) Microwave Promoted Synthesis of Some Schiff Bases. Archives of Applied Science Research, 2, 221-224.
[13]  Shntaif, A.H. and Rashid, Z.M. (2016) The Synthesis of Schiff Bases under Microwave Irradiation: Review. Journal of Chemical and Pharmaceutical Science, 9, 1066-1068.
[14]  Rao, V.K., Reddy, S.S., Krishna, B.S., Naidu, K.R.M., Raju C.N. and Ghosh, S.K. (2010) Synthesis of Schiff’s Base in Aqueous Medium: A Green Alternative Approach with Effective Mass Yield and High Reaction Rates. Green Chemistry Letters and Reviews, 3, 217-223.
[15]  Oforka, N.C. and Mkpenie, V.N. (2003) A New Method of Synthesis of Azo Schiff Base Ligands with Azo and Azomethine Donors: Synthesis of N-4-Methoxy-benzy-lidene-2-(3-hydroxyphenylazo)-5-hydroxyaniline and Its Nickel (II) Complex. Chinese Journal of Chemistry, 25, 869-871.
[16]  Dincalp, H., Toker, F., Durucasu, I., Avcibasi, N. and Icli, S. (2007) New Thiophene-Based Azo Ligands Containing Azo Methine Group in the Main Chain for the Determination of Copper (II) Ions. Dyes and Pigments, 75, 11-24.
[17]  Aslantas, M., Kurtoglu, N., Sahin, E. and Kurtoglu, M. (2007) 4-[(E)-Phenyldiaze-ny]-2-[(E)-phenyl-iminomethyl]phenol. Acta Crystallographica Section E, 63, o3637.
[18]  Ispir, E. (2009) The Synthesis, Characterization, Electrochemical Character, Catalytic and Antimicrobial Activity of Novel, Azo-Containing Schiff Bases and Their Metal Complexes. Dyes and Pigments, 82, 13-19.
[19]  Yahyazadeh, A. and Azimi, V. (2012) Synthesis of Some Unsymmetrical New Schiff Bases from Azo Dyes. European Chemical Bulletin, 2, 453-455.
[20]  Nikpassand, M., Fekri, L.Z. and Sharafi, S. (2013) An Efficient and Green Synthesis of Novel Azo Schiff Base and Its Complex under Ultrasonic Irradiation. Oriental Journal of Chemistry, 29, 1041-1046.
[21]  Helal, T.A., Abbas, G.J. and Mohammed, F.H. (2014) Synthesis and Identification of New 4-Amino Phenazone Derivatives Containing Azo Group. International Journal of Multidisciplinary Research and Development, 1, 41-45.
[22]  Shreekanta, S.A., Venkatesh, T.V., Parameshwara, P.N. and Shoba, K.S. (2014) Electrosynthesis, Electrochemical Behaviour, Antibacterial and Antifungal Activity of Novel Azo-Schiff’s Bases. Indian Journal of Applied Research, 4, 91-95.
[23]  Khanmohammadi, H. and Darvishpour, M. (2009) New Azo Ligands Containing Azomethine Groups in the Pyridazine-Based Chain: Synthesis and Characterization. Dyes and Pigments, 81, 167-173.
[24]  Eissa, H.H. (2013) Synthesis and Characterization of New Azo-Schiff Bases and Study Biological Activity. Journal of Current research in Science, 1, 444-450.
[25]  Fekri, M.H., Darvishpour, M., Khanmohammadi, H. and Rashidipour, M. (2013) Synthesis and Biological Activity of a New Schiff Base Ligand Pyridazine Based. Journal of Chemical Health Risks, 3, 63-68.
[26]  Kumar, H. and Chaudhary, R.P. (2010) Pesticidal Studies of An Azo Based Hetercyclic Schiff Base and Its Transition Metal Complexes. Archives of Applied Science Research, 2, 407-413.
[27]  Mahdi, R.T., Ali, A.M. and Noaman, H.A. (2014) Preparation and Characterization of Some Metal Complexes with New Heterocyclic Schiff-Azo Ligand. Journal of Al-Nahrain University, 17, 51-58.
[28]  Al Hamdani, A.A.S., Balkhi, A., Falah, A. and Shaker, S.A. (2015) New Azo-Schiff Base Derived with Ni(II), Cu(II), Pd(II) and Pt(II) Complexes: Preparation, Spectroscopic Investigation, Structural Studies and Biological Activity. Journal of Chilean Chemical Society, 60, 2774-2785.
[29]  Mehta, K.K. and Patel, A.D. (2016) Synthesis, Characterization, Biological and Chelating Properties of New Antipyrine Derived Azo Dyes and Its Transition Metal Complexes. Acta Chimica and Pharmaceutica Indica, 6, 26-31.
[30]  Tapabashi, N.O., Al-Janabi, K.M. and Mohammed, S.A. (2017) Thermal Performance, Photostability and UV-Visible Spectroscopic Studies of Some Synthesized Azo-Schiff and Bisazo-Schiff Bases. International Journal of Engineering and Advanced Research Technology, 3, 19-31.
[31]  Li, G., Mark, M.F., Lv, H., McCamant, D.W. and Eisenberg, R. (2018) Rhodamine-Platinum Diimine Dithiolate Complex Dyads as Efficient and Robust Photosensitizers for Light-Driven Aqueous Proton Reduction to Hydrogen. Journal of American Chemical Society, 140, 2575-2586.
[32]  Lewis, N.S. (2005) Chemical Control of Charge Transfer and Recombination at Semiconductor Photoelectrode Surfaces. Inorganic Chemistry, 44, 6900-6911.
[33]  Crabtree, G.W. and Lewis, N.S. (2007) Solar Energy Conversion. Physics Today, 60, 37-42.
[34]  Ayoob, M.M. (2016) Design, Synthesis and Spectroscopic Study of Some New Flavones Containing Two Azo Linkages. M.Sc. Thesis, Salahaddin University, Erbil.
[35]  El-Bayoumi, M.A., El-Asser, M. and Abdel-Halim, F. (1971) Electronic Spectra and Structure of Schiff’s Base. I. Benzanils. Journal of American Chemical Society, 93, 586-590.
[36]  Saeed, A.A.H. (1979) Spectroscopic Evidence for the Presence of Mono- and Di-Protonated Species of p-N, N-Dimethylaminobenzylideneaniline and Its p’-Substituted Derivatives. Indian Journal of Chemistry, 17, 105-107.
[37]  Saeed, A.A.H. (1980) The Effect of Conjugation on the First Two Electronic Transition in Some P- and P’-Substituted Benzylideneaniline. Iraqi Journal of Chemistry, 21, 104-114.
[38]  Patai, S. (1970) The Chemistry of the Carbon-Nitrogen Double Bond. John Wiley & Sons Ltd., New York.
[39]  Nief, O.A. (2013) Photostabilization of Poly (Vinyl Chloride) by Some Schiff Base Derived from 2-Amino Pyridine. Journal of Al-Nahrain University, 16, 18-28.
[40]  Yousif, E., Al-Amiery, A.A., Kadihum, A., Kadhum, A.A. and Mohemad, A.B. (2015) Photostabilizing Efficiency of PVC in the Presence of Schiff Bases as Photostabilizers. Molecules, 20, 19886-19899.


comments powered by Disqus