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Synthesis of N2O2N Azacrown Macrocyclic Ligands and Comparative Study on the Complexation of Ligands with [60]Fullerene and Cu(II)

Shahhosseini, Leila | 2013

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  1. Type of Document: M.Sc. Thesis
  2. Language: Farsi
  3. Document No: 45068 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Ghanbari, Bahram
  7. Abstract:
  8. By considering previous experiments undertaken in our laboratory on O2Nx (x=2,3) azacrown complexes with [60]fullerene, it was found that factors such as the macroring size, type and number of the donors groups in these macrocyclic ligands had significant effects on their selectivity towards [60]fullerene complexation. In this research, three N2O2N–azacrown macrocyclic ligand having uniform distribution of nitrogen atoms in macroring was synthesized using direct synthesis and high dilution method. The products were characterized applying 1H and 13C NMR spectroscopy as well as elemental analysis. Interaction of these ligands with [60]fullerene and Cu(II) were monitored by UV-vis spectroscopy and applying Benesi-Hildebrand equation. These intercations was compared in terms of their calculated association constants (Ka) obtained for O2N2 and O2N3 macrocyclic ligands in previous experiments . Ka values for N2O2N azacrowns was close to the same size O2N2 macrocycle while was less than the relative O2N3 macrocycle . These results confirmed on importance of the number of the secondary amine groups in the aformantation complexation with [60]fullerene. Also modeling studies applying PM3 method using chem office software, showed that the intimate approach of the aromatic ring moieties of N2O2N azacrowns towards the external surface of [60]fullerene would be the best candidate for the observed intercations
  9. Keywords:
  10. Fullerene ; Macrocyclic Ligand ; Azacrown ; Complexation

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