Water-soluble host-guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

Si-Yuan Liu; Xin-Rui Wang; Man-Ping Li; Wen-Rong Xu; Dietmar Kuck

doi:10.3762/bjoc.16.207

Water-soluble host-guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

Beilstein J Org Chem. 2020 Oct 14:16:2551-2561. doi: 10.3762/bjoc.16.207. eCollection 2020.

Authors

Si-Yuan Liu¹, Xin-Rui Wang¹, Man-Ping Li¹, Wen-Rong Xu¹, Dietmar Kuck²

Affiliations

¹ Key Laboratory of Advanced Materials of Tropical Island Resources of Ministry of Education, Hainan Provincial Key Laboratory of Fine Chemistry, Department of Chemistry, School of Science, Hainan University, Haikou, 570228, China.
² Department of Chemistry, Center for Molecular Materials (CM2), Bielefeld University, 33615 Bielefeld, Germany.

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 the complexes TBTQ-(OG) ₆ with C₆₀ and TBTQ-(OG) ₆ with C₇₀ was found to be 1:1 with binding constants of K _a = (1.50 ± 0.10) × 10⁵ M^-1 and K _a = (2.20 ± 0.16) × 10⁵ M^-1, respectively. The binding affinity between TBTQ-(OG) ₆ and C₆₀ was further verified by Raman spectroscopy. The geometry of the complex of TBTQ-(OG) ₆ with 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 and 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: fullerenes; host–guest systems; microspheres; supramolecular chemistry; tribenzotriquinacene.

Grants and funding

The following sources of funding are acknowledged: High-level Talent Program of Hainan Province (No. 2019RC156), Scientific Research Start-up Foundation of Hainan University (No. kyqd1635) and NSFC (No. 22061015, No. 21978059, No. 21801053).