Abstract

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 K_a = 3.7 × 10⁴ M^–1 and K_a = 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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