Synthesis of Azacrown Macrocyclic Ligand with Pendant Arms and Study of Their Complexation with [60] Fullerene and Cu(II) Cation

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Kazemi, Ameneh | 2016

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Type of Document: M.Sc. Thesis
Language: Farsi
Document No: 48894 (03)
University: Sharif University of Technology
Department: Chemistry
Advisor(s): Ghanbari, Bahram
Abstract:
In this research, four N2O2–azacrown macrocyclic ligands with naphthalene pendant arms (L1-L4) were synthesized using direct synthesis. The products were characterized applying 1H and 13C {1H} NMR spectroscopy, IR and Mass spectrometry. Interaction of these ligands with [60]fullerene and Cu(II) were monitored respectively by fluorescent as well as UV-vis spectroscopy and applying Benesi-Hildebrand equation. These intercations were compared with N2O2 macrocyclic ligands in previous experiments in terms of their calculated association constants (Ka). According to our results, the presence of naphthalene pendant arm groups led to increase the interaction with [60]fullerene compared to the initial macrocycl. Furthermore interaction of these ligands with various metal cations were studied employing fluorescence spectroscopy. The results for L1 and L2 showed significant selectivity for Cr(III) and Fe(II), respectively. Moreover, modeling studies applying SPARTAN software and DFT calculations using B3LYP/6-31G* basis set that in these complexes with [60]fullerene showed HOMO and LUMO are on the ligand and [60]fullerene, respectively
Keywords:
Azacrown ; Macrocycle ; Fullerene C60 ; Macrocyclic Ligand ; Pendant Arm Groups

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