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Vol. 30 No. 12 (2018): Vol 30 Issue 12

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New Metallacyclic Derivatives of Aluminium(III) Stabilized with Bi- and Tridentate Chelating Ligands as Ring Opening Polymerization Catalysts of ε-Caprolactone

https://doi.org/10.14233/ajchem.2018.21727
Vuppalapati Giri Prasanth
School of Science and Humanities, Vel Tech Rangarajan Dr. Sagunthala R&D Institute of Science and Technology, Avadi, Chennai-600 062, India
Madhvesh Pathak
School of Advanced Sciences, Vellore Institute of Technology, Vellore-632 014, India

Corresponding Author(s) : Madhvesh Pathak

madhveshpathak@vit.ac.in

Asian Journal of Chemistry, Vol. 30 No. 12 (2018): Vol 30 Issue 12

Abstract

A family of four metallo-organic derivatives of aluminium(III) [(L)Al(CH3COCHCOOCH3)] (1-4) were synthesized by treating Al(OPri)3 with methyl acetoacetate and tridentate Schiff's base chelating ligand H2Lx (H2L1 = C13H11NO2; H2L2 = C13H10NO2Br; H2L3 = C14H13NO3; H2L4 = C17H13NO2) in 1:1:1 stoichiometry using mixture of anhydrous ethanol and benzene as solvent. The yellow coloured solid compounds obtained were characterized by FTIR, elemental analysis and NMR (1H and 13C) spectra. Complexes 1, 2 and 3 appeared as adducts with one mole of ethanol. As both the ligands used were asymmetric, the two possible structural isomers were well evidenced from NMR (1H and 13C) analysis. Furthermore, all the four heteroleptic derivatives of aluminium(III) were systematically screened as catalysts in ring opening polymerization of ε-caprolactone. Derivative 4 bearing bulky Schiff′s base ligand was not active in polymerizing ε-caprolactone. The molecular weights and the polydispersity index values of polymers prepared were acquired by GPC analysis. The superior catalytic activity of complex 2 was rationalized by the presence of strong electronegative bromine atom.

Keywords

Heavy metals Toxic effects Cosmetics Foundation creams
Prasanth, V. G., & Pathak, M. (2018). New Metallacyclic Derivatives of Aluminium(III) Stabilized with Bi- and Tridentate Chelating Ligands as Ring Opening Polymerization Catalysts of ε-Caprolactone. Asian Journal of Chemistry, 30(12), 2797–2802. https://doi.org/10.14233/ajchem.2018.21727
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References
  1. C. Pérez-Bolívar, L. Llovera, S.E. Lopez and P.J. Anzenbacher Jr., J. Lumin., 130, 145 (2010); https://doi.org/10.1016/j.jlumin.2009.08.004.
  2. P.K. Nayak, N. Agarwal, F. Ali, M.P. Patankar, K.L. Narasimhan and N. Periasamy, J. Chem. Sci., 122, 847 (2010); https://doi.org/10.1007/s12039-010-0073-0.
  3. C. Pérez-Bolívar, S. Takizawa, G. Nishimura, V.A. Montes and P.J. Anzenbacher Jr., Chem. Eur. J., 17, 9076 (2011); https://doi.org/10.1002/chem.201100707.
  4. W.A. Omar, J. Adv. Res., 4, 525 (2013); https://doi.org/10.1016/j.jare.2012.09.003.
  5. A.R. Sanwaria, N. Sharma, A. Chaudhary and M. Nagar, J. Sol-Gel Sci. Technol., 68, 245 (2013); https://doi.org/10.1007/s10971-013-3160-0.
  6. A.R. Sanwaria, M. Nagar, R. Bohra, A. Chaudhary, S.M. Mobin, P. Mathur and B.L. Choudhary, RSC Adv., 4, 30081 (2014); https://doi.org/10.1039/C4RA03245D.
  7. Y.C. Liu, B.T. Ko and C.C. Lin, Macromolecules, 34, 6196 (2001); https://doi.org/10.1021/ma0104579.
  8. D.J. Darensbourg, O. Karroonnirun and S.J. Wilson, Inorg. Chem., 50, 6775 (2011); https://doi.org/10.1021/ic2008057.
  9. L.M. Alcazar-Roman, B.J. O’Keefe, M.A. Hillmyer and W.B. Tolman, Dalton Trans., 15, 3082 (2003); https://doi.org/10.1039/B303760F.
  10. M. Bouyahyi, E. Grunova, N. Marquet, E. Kirillov, C.M. Thomas, T. Roisnel and J.F. Carpentier, Organometallics, 27, 5815 (2008); https://doi.org/10.1021/om800651z.
  11. N. Nomura, A. Akita, R. Ishii and M. Mizuno, J. Am. Chem. Soc., 132, 1750 (2010); https://doi.org/10.1021/ja9089395.
  12. M.M. Kireenko, E.A. Kuchuk, K.V. Zaitsev, V.A. Tafeenko, Y.F. Oprunenko, A.V. Churakov, E.K. Lermontova, G.S. Zaitseva and S.S. Karlov, Dalton Trans., 44, 11963 (2015); https://doi.org/10.1039/C5DT01001B.
  13. H. Pei, H. Yang, N. Lu, W. Liu and Y. Li, Z. Anorg. Allg. Chem., 643, 511 (2017); https://doi.org/10.1002/zaac.201600464.
  14. J. Melendez, M. North and P. Villuendas, Chem. Commun. (Camb.), 18, 2577 (2009); https://doi.org/10.1039/b900180h.
  15. M. North and C. Young, Catal. Sci. Technol., 1, 93 (2011); https://doi.org/10.1039/c0cy00023j.
  16. C.J. Whiteoak, N. Kielland, V. Laserna, E.C. Escudero-Adán, E. Martin and A.W. Kleij, J. Am. Chem. Soc., 135, 1228 (2013); https://doi.org/10.1021/ja311053h.
  17. J. Wu, T.L. Yu, C.T. Chen and C.C. Lin, Coord. Chem. Rev., 250, 602 (2006); https://doi.org/10.1016/j.ccr.2005.07.010.
  18. R.K. Mehrotra and R.C. Mehrotra, Can. J. Chem., 39, 795 (1961); https://doi.org/10.1139/v61-097.
  19. R.K. Gupta, A. Jain and S. Saxena, Main Group Met. Chem., 32, 65 (2009); https://doi.org/10.1515/MGMC.2009.32.2.65.
  20. J. Bhomia, J. Sharma and Y. Singh, Main Group Met. Chem., 39, 151 (2016); https://doi.org/10.1515/mgmc-2015-0035.
  21. R. Lichtenberger, M. Puchberger, S.O. Baumann and U. Schubert, J. Sol-Gel Sci. Technol., 50, 130 (2009); https://doi.org/10.1007/s10971-008-1890-1.
  22. D. Bradley, R.C. Mehrotra, I. Rothwell and A. Singh, Alkoxo and Aryloxo Derivatives of Metals, Elsevier: Amsterdam (2001).
  23. A. Saini, V. Dhayal and D.C. Agarwal, Surf. Coat. Technol., 335, 241 (2018); https://doi.org/10.1016/j.surfcoat.2017.12.020.
  24. Y.A. Piskun, I.V. Vasilenko, K.V. Zaitsev, Y.F. Oprunenko and S.V. Kostjuk, Macromol. Chem. Phys., 218, 1600580 (2017); https://doi.org/10.1002/macp.201600580.
  25. J. Wei, M.N. Riffel and P.L. Diaconescu, Macromolecules, 50, 1847 (2017); https://doi.org/10.1021/acs.macromol.6b02402.
  26. C.T. Chen, C.A. Huang and B.H. Huang, Dalton Trans., 19, 3799 (2003); https://doi.org/10.1039/B307365C.
  27. M.L. Hsueh, B.H. Huang and C.C. Lin, Macromolecules, 35, 5763 (2002); https://doi.org/10.1021/ma020574j.
  28. Y.N. Chang, P.Y. Lee, X.R. Zou, H.F. Huang, Y.W. Chen and L.C. Liang, Dalton Trans., 45, 15951 (2016); https://doi.org/10.1039/C6DT02143C.
  29. R.K. Dubey, Meenakshi and A.P. Singh, Main Group Met. Chem., 38, 17 (2015); https://doi.org/10.1515/mgmc-2014-0038.
  30. C. Robert, T.E. Schmid, V. Richard, P. Haquette, S.K. Raman, M.-N. Rager, R.M. Gauvin, Y. Morin, X. Trivelli, V. Guérineau, I. del Rosal, L. Maron and C.M. Thomas, J. Am. Chem. Soc., 139, 6217 (2017); https://doi.org/10.1021/jacs.7b01749.
  31. M.S. Liberato, S. Kogikoski, E.R. da Silva, D.R. de Araujo, S. Guha and W.A. Alves, J. Mater. Chem. B Mater. Biol. Med., 4, 1405 (2016); https://doi.org/10.1039/C5TB02240A.
  32. E. Malikmammadov, T.E. Tanir, A. Kiziltay, V. Hasirci and N. Hasirci, J. Biomater. Sci. Polym. Ed., 29, 863 (2018); https://doi.org/10.1080/09205063.2017.1394711.
  33. G.G. Briand, T. Chivers and M. Krahn, Coord. Chem. Rev., 233-234, 237 (2002); https://doi.org/10.1016/S0010-8545(02)00033-4.
  34. H.V. Huynh, T.C. Neo and G.K. Tan, Organometallics, 25, 1298 (2006); https://doi.org/10.1021/om0510369.
  35. C.Y. Liao, K.T. Chan, Y.C. Chang, C.Y. Chen, C.Y. Tu, C.H. Hu and H.M. Lee, Organometallics, 26, 5826 (2007); https://doi.org/10.1021/om700607m.
  36. D.D. Perrin, Purification of Laboratory Chemicals, Pergamon Press: New York, edn 2 (1980).
  37. T. Sedaghat and F. Shafahi, Main Group Chem., 8, 1 (2009); https://doi.org/10.1080/10241220902962895.
  38. Z.D. Petrovic, J. Dorovic, D. Simijonovic, V.P. Petrovic and Z. Markovic, RSC Adv., 5, 24094 (2015); https://doi.org/10.1039/C5RA02134K.
  39. S.M. Islam, R.C. Dey, A.S. Roy, S. Paul and S. Mondal, Transition Met. Chem., 39, 961 (2014); https://doi.org/10.1007/s11243-014-9881-2.
  40. W. Wang, T. Vanderbeeken, D. Agustin and R. Poli, Catal. Commun., 63, 26 (2015); https://doi.org/10.1016/j.catcom.2014.08.018.
  41. M.M. Abo-Aly, A.M. Salem, M.A. Sayed and A.A. Abdel Aziz, Spectrochim. Acta A Mol. Biomol. Spectrosc., 136, 993 (2015); https://doi.org/10.1016/j.saa.2014.09.122.
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