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Synthesis and Characterization of a Metal-Organic Molecular Cage with Anthracene Derivative Linkers and the Study of its Host-Guest Chemistry

Daemi, Zohreh | 2025

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  1. Type of Document: M.Sc. Thesis
  2. Language: Farsi
  3. Document No: 57906 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Jamali, Sirous
  7. Abstract:
  8. Through the bromination reaction of anthracene, the compound 9,10-dibromoanthracene (1) was synthesized. Subsequently, using a Suzuki coupling mechanism and the pinacol ester of 4-pyridineboronic acid, the ligand 9,10-bis(4-pyridyl)anthracene (2) was obtained. A cubic molecular cage [(PtMe3)8(9,10-bis(4-pyridyl)anthracene)12][OTf]8 (5) with trimethylplatinum(IV) (PtMe3) vertices and anthracene-based linkers was synthesized from the reaction of [PtMe3I]4 (3) with 9,10-bis (4-pyridyl)anthracene(2) linker in the presence of AgOTF (OTf = trifluoromethanesulfonate) in a 1:6 molar ratio. The structure of 5 was characterized by NMR spectroscopy in solution state. The ratio of aromatic to aliphatic peaks in the 1H NMR spectrum confirms the cubic structure of 5. Additionally, the 2D-NOESY NMR spectrum reveals the interaction between the methyl groups attached to platinum and the pyridyl hydrogens in the aromatic region. Cage 5, due to the electron-donating nature of anthracene, can serve as a suitable host for electron-accepting molecules such as fullerene. Therefore, its host-guest chemistry with fullerene (C60) was investigated. Upon interaction with fullerene, the NMR spectra of the cage changed, and the peaks became sharper, indicating that the cage structure became more rigid and the rotation around the C–C and Pt–N bonds was restricted. Additionally, the absorption and emission spectra of cage 5 and its host-guest complex with fullerene (C60) were studied in solution. The absorption spectrum of cage 5 exhibits the absorption pattern of the ligand with enhanced intensity. In the host-guest absorption spectrum, a hump corresponding to fullerene absorption is also observed. Cage 5 shows blue emission in solution, which shifts to yellow upon interaction with fullerene. In the solid state, compound 5 exhibits strong blue emission, which is quenched in the presence of fullerene and does not show any emission
  9. Keywords:
  10. Anthracene ; Host-Guest Complex ; Fullerene ; Suzuki Coupling ; Molecular Cage ; Metal-Organic Cages

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