A sugar-functionalized water-soluble tribenzotriquinacene derivative bearing six glucose residues, TBTQ-(OG)6, was synthesized and its interaction with C60- and C70-fullerene in co-organic solvents and aqueous solution was investigated by fluorescence spectroscopy and ultraviolet-visible spectroscopy. The association stoichiometry of TBTQ-(OG)6 ⊂ C60 and TBTQ-(OG)6 ⊂ C70 was found to be 1 : 1 with binding constants of Ka = 3.7 × 104 M–1 and Ka = 8.5 × 104 M–1, respectively. The binding affinity between TBTQ-(OG)6 and C60 was further verified by Raman spectroscopy. The geometry of TBTQ-(OG)6 ⊂ C60 deduced from DFT calculations indicates that the driving force of the complexation is mainly due to the hydrophobic effect and to host-guest π-π interactions. Hydrophobic surface simulations showed that TBTQ-(OG)6 ⊂ C60 forms an amphiphilic supramolecular host-guest complex, which further assembles to microspheres with diameters of 0.3–3.5 μm, as determined by scanning electron microscopy.
Keywords: Tribenzotriquinacene; Host-guest systems; Supramolecular chemistry; Fullerenes; Microspheres
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Liu, S.-Y.; Wang, X.-R.; Li, M.-P.; Xu, W.-R.; Kuck, D. Beilstein Arch. 2020, 202074. doi:10.3762/bxiv.2020.74.v1
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