Article Versions
Export Article
Research Article
Open Access Peer-reviewed

An Undergraduate Experiment Using Microwave-Assisted Synthesis of First Raw Metalloporphyrins: Characterizations and Spectroscopic Study

Muna Bufaroosha1,, Shaikha S. Al Neyadi1, Mohamed A.R. Alnaqbi1, Sayed A.M. Marzouk1, Abdullah Al-Hemyari1, Bashar Yousef Abuhattab1, Dana Akram Adi1

1Department of Chemistry, College of Science, UAE University, Al-Ain, UAE

World Journal of Chemical Education. 2019, 7(3), 225-231. DOI: 10.12691/wjce-7-3-6
Received July 19, 2019; Revised August 21, 2019; Accepted September 20, 2019

Abstract

There is a notable absence in the practical inorganic curricula for experiments in which students can synthesize and characterize series of inorganic complexes. This is possibility attributed to the long required time which is not normally available in regular lab sessions. To address this absence, this paper describes a two-part experiment for chemistry major students in which they prepare series of metalloporphyrins using microwave-assisted technique. In addition to its attractive simplicity, microwave-assisted preparation substantially reduces the needed reaction time to suit the lab session duration. The first lab session is dedicated to the characterization of the 5,10,15,20-tetraphenylporphyrin (TPP) as well as the synthesis of the corresponding Fe(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes. The second session involves the spectroscopic characterization (UV-vis, 1H-NMR, and IR) of the prepared metalloprophyrins. The students relate the experimental results with the provided theoretical data based on quantum chemical calculations.

Keywords:

Metalloporphyrins Frontiers Orbitals, metalloporphyrins electronic structure, metalloporphyrins microwave-assisted synthesis
[1]  Auwarter W., E.D., Klappenberger F., Barth G. V., Nature Chemistry, 2017. 7: p. 105-120.View Article  PubMed 
 
[2]  Kadish K.M., S.K.M., Guilard R., Bioinorganic and Bioorganic Chemistry. In The Porphyrin Handbook. Vol. 11. 2003, San Diego, CA, USA. 1-277.
 
[3]  Kadish K.M., S.K.M., Guilard R., Biochemistry and Binding: Activation of Small Molecules. In The Porphyrin Handbook. Vol. 4. San Diego, CA, USA.
 
[4]  Imran M., R.M., Qureshi A. K., Khan M. A., Tariq M., Biosensors, 2018. 8: p. 95.View Article  PubMed  PubMed 
 
[5]  Chou J., K.M.E., Nalwa H. S, Rakow N. A., Journal of Porphyrins and Phthalocyanines, 2000. 4(4): p. 407-413.
 
[6]  Nagarajan S., B.F.F., Samuelson L., Kumar J., Nagarajan R., Metalloporphyrin based Biomimetic Catalysts for Materials Synthesis and Biosensing. Biomaterials, 2010. 1054: p. 221-242.View Article 
 
[7]  Alexandre F-R, D.L., Frère S, Testard A and Thiéry V., Mol. Diversity 2003. 7: p. 237-280View Article  PubMed 
 
[8]  Neyadi, S.S.A., Alzamly, A., Al-Hemyari, A., Tahir, I. M., Al-Meqbali, S., Ahmad, M. A. A., & Bufaroosha, M., An Undergraduate Experiment Using Microwave-Assisted Synthesis of Metalloporphyrins: Characterization and Spectroscopic Investigations. World Journal of Chemical Education, 2019.
 
[9]  Rocha Gonsalves, A.M.d.A., Varejão, J. M. T. B., Pereira, M., Some New Aspects Related to the Synthesis of meso-Substituted Porphyrins. Journal of Heterocyclic Chemistry, 1991. 28: p. 635-640.View Article 
 
[10]  Rocha Gonsalves, A.M.d.A.V., J. M. T. B.; Pereira, M. M. , J. Heterocyclic Chem., 1991. 28: p. 286.View Article 
 
[11]  Mamardashvili, G.M., Simonova, O. R., Chizhova, N. V., & Mamardashvili, N. Zh., Influence of the Coordination Surrounding of Co(II)- and Co(III)-Tetraphenylporphyrins on Their Destruction Processes in the Presence of Organic Peroxides. Russian Journal of General Chemistry, 2018. 88(6): p. 1154-1163.View Article 
 
[12]  Liao, M.S., Scheiner, S., J. Chem. Phys, 2002. 117(1): p. 205-219.View Article 
 
[13]  Gouterman M., Dolphin D., Ed., The Porphyrins. Academic, N. Y., 1978. 3: p. 1.View Article 
 
[14]  Hu C., N.B.C., Schulz C. E., and Scheidt W. R., Four-Coordinate Iron(II) Porphyrinates: Electronic Configuration Change by Intermolecular Interaction. Inorg Chem. 2007. 46(3): p. 619-621.View Article  PubMed  PubMed 
 
[15]  R. B. King, R.H.C., C. M. Lukehart, D. A. Atwood, & R. A. Scott (Eds.), Iron Porphyrin Chemistry, in Encyclopedia of Inorganic Chemistry. 2006, Walker, F. A., & Simonis. p. 2390-2521.
 
[16]  F. Ann Walker, U.S., Iron Porphyrin Chemistry in in Encyclopedia of Inorganic Chemistry, R.B. King, Editor. 2005, John Wiley & Sons: Ltd, Chichester, p. 2390-2521.
 
[17]  Sun Z.C., S.Y.B., Zhou Y., Song X.F., Li, K., Synthesis, Characterization and Spectral Properties of Substituted Tetraphenylporphyrin Iron Chloride Complexes. Molecules, 2011. 16(4): p. 2960-2970.View Article  PubMed  PubMed 
 
[18]  Walker, F.A.W., NMR and EPR spectroscopy of Paramagnetic Metalloporphyrins and Heme Proteins. Handbook of Porphyrin Science. Vol. 6. 2010.View Article  PubMed 
 
[19]  Walker, F.A., Inorg. Chem., 2003. 42: p. 4526-4544.View Article  PubMed