Synthesis and Characterization of 2,2’-Bipyridyl-5,5’-Dialdehyde Schiff Bases from O,S,N and F-Containing Amines
Affiliation(s)
1 Department of Chemistry, Tennessee State University, Nashville, TN, USA. 2 Department of Chemistry, Iowa State University, Ames, IA, USA. 3 Chemistry, Faculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link, Brunei Darussalam.
1 Department of Chemistry, Tennessee State University, Nashville, TN, USA. 2 Department of Chemistry, Iowa State University, Ames, IA, USA. 3 Chemistry, Faculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link, Brunei Darussalam.
ABSTRACT
Design and synthesis of organic chelating agents containing nitrogen and sulfur as donor atoms and their metal complexes is an interesting field of research for their different types of activities. The bi-dentate N,N chelating agent such as 2,2-Bipyridal has been playing a vital role in synthetic and medicinal chemistry. 2,2-Bipyridal has been used to prepare many mixed-ligand complexes. Different ligand complexes prepared from 2,2-Bipyridyl are used in different areas such as molecular catalysis, solar energy conversion, calorimetric analysis, herbicides, molecular recognition, self-assembly, antineoplastic agents, and nucleic acid probes. Another important property of these types of compounds is the triplet state photosensitizing character of bipyridyl nucleus, which is shown in metal complexes. It is also found that compounds containing O,S,N atoms have received considerable attention because of their pharmacological studies like anticancer, antibacterial, and antitumour activities. Therefore, it has been decided to synthesize Schiff bases derived from 2,2’- bipyridyl-5,5’-dicarbaldehyde compounds with O,S,N and F-containing amines and study their antibacterial properties. Several new Schiff bases have been synthesized and fully characterized by spectral data. This paper presents the synthesis and characterization of newly designed Schiff bases.
Design and synthesis of organic chelating agents containing nitrogen and sulfur as donor atoms and their metal complexes is an interesting field of research for their different types of activities. The bi-dentate N,N chelating agent such as 2,2-Bipyridal has been playing a vital role in synthetic and medicinal chemistry. 2,2-Bipyridal has been used to prepare many mixed-ligand complexes. Different ligand complexes prepared from 2,2-Bipyridyl are used in different areas such as molecular catalysis, solar energy conversion, calorimetric analysis, herbicides, molecular recognition, self-assembly, antineoplastic agents, and nucleic acid probes. Another important property of these types of compounds is the triplet state photosensitizing character of bipyridyl nucleus, which is shown in metal complexes. It is also found that compounds containing O,S,N atoms have received considerable attention because of their pharmacological studies like anticancer, antibacterial, and antitumour activities. Therefore, it has been decided to synthesize Schiff bases derived from 2,2’- bipyridyl-5,5’-dicarbaldehyde compounds with O,S,N and F-containing amines and study their antibacterial properties. Several new Schiff bases have been synthesized and fully characterized by spectral data. This paper presents the synthesis and characterization of newly designed Schiff bases.
Cite this paper
Hoq, M. , Karim, M. , Arifuzzaman, M. and Mirza, A. (2015) Synthesis and Characterization of 2,2’-Bipyridyl-5,5’-Dialdehyde Schiff Bases from O,S,N and F-Containing Amines. International Journal of Organic Chemistry, 5, 29-36. doi: 10.4236/ijoc.2015.51004.
Hoq, M. , Karim, M. , Arifuzzaman, M. and Mirza, A. (2015) Synthesis and Characterization of 2,2’-Bipyridyl-5,5’-Dialdehyde Schiff Bases from O,S,N and F-Containing Amines. International Journal of Organic Chemistry, 5, 29-36. doi: 10.4236/ijoc.2015.51004.
References
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http://dx.doi.org/10.1021/jp020927g [13] Gomathi, V., Selvameena, R., Subbalakshmi, R. and Valarmathy, G. (2013) Synthesis, Spectral Characterization and Antimicrobial Screening of Mn(ll) and Zn(ll) Complexes Derived from (E)-1-((p-tolylimino)methyl)naphthalene-2-ol. Oriental Journal of Chemistry, 29, 533-538. [14] Wang, J., Onions, S., Pilkington, M., Stoeckli-Evans, H., Halfpenny, J.C. and Wallis, J.D. (2007) Metal Catalyzed Rearrangement of a 2,2-Bipyridine Schiff-Base Ligand to a Quaterpyridine-Type Complex. Chemical Communications, 2007, 3628-3630.
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[1] Siebert, R., Winter, A., Dietzek, B., Schubert, U.S. and Popp, J. (2010) Dual Emission from Highly Conjugated 2,2’:6’:2”-Terpyridine Complexes—A Potential Route to White Emitters. Macromolecular Rapid Communications, 31, 883-888.
http://dx.doi.org/10.1002/marc.200900894 [2] Siebert, R., Winter, A., Schubert, U.S., Dietzek, B. and Popp, J. (2010) Excited-State Planarization as Free Barrierless Motion in a π-Conjugated Terpyridine. The Journal of Physical Chemistry C, 114, 6841-6848.
http://dx.doi.org/10.1021/jp100313x [3] Siebert, R., Winter, A., Schubert, U.S., Dietzek, B. and Popp, J. (2011) The Molecular Mechanism of Dual Emission in Terpyridine Transition Metal Complexes—Ultrafast Investigations of Photoinduced Dynamics. Physical Chemistry Chemical Physics, 13, 1606-1617.
http://dx.doi.org/10.1039/C0CP01134G [4] Binnemans, K., Lenaerts, P., Driesen, K. and Gorller-Walrand, C. (2004) A Luminescent Tris(2-thenoyltrifluoroacetonato)europium(III) Complex Covalently Linked to a 1,10-Phenanthroline-functionalised Sol-Gel Glass. Journal of Materials Chemistry, 14, 191-195.
http://dx.doi.org/10.1039/b311128h [5] Larsson, K. and Ohrstrom, L. (2004) X-ray and NMR Study of the Fate of the Co(1,10-phenanthroline-5,6-diketone)33+ Ion in Aqueous Solution: Supramolecular Motifs in the Packing of 1,10-Phenanthroline-5,6-diketone and 1,10-Phenanthroline-5,6-diol Complexes. Inorganica Chimica Acta, 357, 657-664.
http://dx.doi.org/10.1016/j.ica.2003.07.001 [6] Steed, J.W. and Atwood, J.L. (2000) Supramolecular Chemistry. Wiley, Chichester. [7] Chow, C.S. and Bogdan F.M. (1997) A Structural Basis for RNA—Ligand Interactions. Chemical Reviews, 97, 1489- 1514.
http://dx.doi.org/10.1021/cr960415w [8] Sammes, P.G. and Yahioglu, G. (1994) 1,10-Phenanthroline: A Versatile Ligand. Chemical Society Reviews, 23, 327- 334.
http://dx.doi.org/10.1039/cs9942300327 [9] Balzani, V., Juris, A., Venturi, M., Campagna, S. and Serroni, S. (1996) Luminescent and Redox-Active Polynuclear Transition Metal Complexes. Chemical Reviews, 96, 759-834.
http://dx.doi.org/10.1021/cr941154y [10] Daniel, S. and Gnana Raj, G.A. (2013) Photoinduced Electron-Transfer Reactions of Tris(4,4’-dinonyl-2,2’-bipyridyl) Ruthenium(II) Cation with Phenolate Ions in Aqueous Acetonitrile. Journal of Chemical and Pharmaceutical Research, 5, 220-227. [11] Smith, N.A. and Sadler, P.J. (2013) Photoactivatable Metal Complexes: From Theory to Applications in Biotechnology and Medicine. Philosophical Transactions of the Royal Society A, 373, 20120519.
http://dx.doi.org/10.1098/rsta.2012.0519 [12] Monat, J.E., Rodriguez, J.H. and McCusker, J.K. (2002) Ground- and Excited-State Electronic Structures of the Solar Cell Sensitizer Bis(4,4’-dicarboxylato-2,2’bipyridine)bis(isothiocyanato)ruthenium(II). Journal of Physical Chemistry A, 106, 7399-7406.
http://dx.doi.org/10.1021/jp020927g [13] Gomathi, V., Selvameena, R., Subbalakshmi, R. and Valarmathy, G. (2013) Synthesis, Spectral Characterization and Antimicrobial Screening of Mn(ll) and Zn(ll) Complexes Derived from (E)-1-((p-tolylimino)methyl)naphthalene-2-ol. Oriental Journal of Chemistry, 29, 533-538. [14] Wang, J., Onions, S., Pilkington, M., Stoeckli-Evans, H., Halfpenny, J.C. and Wallis, J.D. (2007) Metal Catalyzed Rearrangement of a 2,2-Bipyridine Schiff-Base Ligand to a Quaterpyridine-Type Complex. Chemical Communications, 2007, 3628-3630.
http://dx.doi.org/10.1039/b705555b [15] Hodacová, J. and Buděsínsky, M. (2007) New Synthetic Path to 2,2’-Bipyridine-5,5’-dicarbaldehyde and Its Use in the [3+3] Cyclocondensation with Trans-1,2-Diaminocyclohexane. Organic Letters, 9, 5641-5643.
http://dx.doi.org/10.1021/ol702612t [16] Sahu, R., Thakur, D.S. and Kashyap, P. (2012) Schiff Base: An Overview of Its Medicinal Chemistry Potential of New Drug Molecules. International Journal of Pharmaceutical Sciences and Nanotechnology, 5, 1757-1764. [17] Reedijk, J. (1987) In: Wilkinson, G., Gillard, R.D. and McCleverty, J.A., Eds., Comprehensive Coordination Chemistry, Vol. 2, Pergamon, Oxford, 73. [18] Arifuzzaman, M., Karim, M.R., Siddiquee1, T.A., Mirza, A.H. and Ali, M.A. (2013) Synthesis and Characterization of New Schiff Bases Formed by Condensation of 2,9-Phenathroline-1,10-dialdehyde with Sulfur-Containing Amines. International Journal of Organic Chemistry, 3, 81-86.