Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres
Siyuan Liu, Xinrui Wang, Man‐Ping Li, Wen‐Rong Xu, Dietmar Kuck
Abstract
A sugar-functionalized water-soluble tribenzotriquinacene derivative bearing six glucose residues, TBTQ-(OG) 6 , was synthesized and its interaction with C 60 and C 70 -fullerene in co-organic solvents and aqueous solution was investigated by fluorescence spectroscopy and ultraviolet-visible spectroscopy. The association stoichiometry of the complexes TBTQ-(OG) 6 with C 60 and TBTQ-(OG) 6 with C 70 was found to be 1:1 with binding constants of K a = (1.50 ± 0.10) × 10 5 M −1 and K a = (2.20 ± 0.16) × 10 5 M −1 , respectively. The binding affinity between TBTQ-(OG) 6 and C 60 was further verified by Raman spectroscopy. The geometry of the complex of TBTQ-(OG) 6 with C 60 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 and C 60 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.