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Synthesis and Characterization of NxOy-Naphthodiazacrowns and Study of Supramolecular Chemistry with C60 and Cu(II)

Jamjah, Ali | 2017

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  1. Type of Document: M.Sc. Thesis
  2. Language: Farsi
  3. Document No: 50315 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Ghanbari, Bahram
  7. Abstract:
  8. New N4O6 molecular tweezers were synthesized from N2O2 benzo- and naphthodiazacrown macrocycles bearing benzylic dialdehydes as a flexible and semi-flexible spacer in a short time and at room temperature. The products were characterized by IR, 1H and 13C NMR spectroscopy as well as elemental microanalysis. The interactions of some of these tweezers with C60, Cu(II), Co(II), Ni(II), Zn(II), Hg(II) and Mn(II) were investigated by employing UV-Vis and fluorescence spectroscopy. Efficient fluorescence responses for 2NM3BD were observed in the presence of C60, Cu(II), Mn(II), Hg(II) and Zn(II). Meanwhile, the calculation of the association constants (K¬BH) employing Benesi-Hildebrand equation in CHCl3 showed remarkable interactions for three molecular tweezers out of five other tweezers. Unlike exo-cooridnated benzodiazacrown ether macrocycles which showed no interactions with C60 as well as transition metal cations in our previous reports, 2BM3BD molecular tweezer exhibited interactions with 2400 and 3420 M-1 for Cu(II) and Co(II) respectively. Moreover, 2BM4BD molecular tweezer illustrated K¬BH value 4000 M-1 with C60. Taking into account that all of those transition metals cations interactions the highest K¬BH value was observed for Hg(II) and 2NM3BD which was 82500 M-1
  9. Keywords:
  10. Macrocycle ; Fullerene ; Naphtadiazacrown ; Exo-Coordinating Macrocycle ; Tweezer ; Molecular Tweezer ; Supramolecular Chemistry

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