Liu Si-Yuan, Wang Xin-Rui, Li Man-Ping, Xu Wen-Rong, Kuck Dietmar
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.
Department of Chemistry, Center for Molecular Materials (CM2), Bielefeld University, 33615 Bielefeld, Germany.
Beilstein J Org Chem. 2020 Oct 14;16:2551-2561. doi: 10.3762/bjoc.16.207. eCollection 2020.
A sugar-functionalized water-soluble tribenzotriquinacene derivative bearing six glucose residues, , was synthesized and its interaction with C and C-fullerene in co-organic solvents and aqueous solution was investigated by fluorescence spectroscopy and ultraviolet-visible spectroscopy. The association stoichiometry of the complexes with C and with C was found to be 1:1 with binding constants of = (1.50 ± 0.10) × 10 M and = (2.20 ± 0.16) × 10 M, respectively. The binding affinity between and C was further verified by Raman spectroscopy. The geometry of the complex of with C 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 and C 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.
合成了一种带有六个葡萄糖残基的糖功能化水溶性三苯并三喹啉衍生物，并通过荧光光谱和紫外可见光谱研究了其在共有机溶剂和水溶液中与C和C富勒烯的相互作用。发现配合物与C以及与C的缔合化学计量比均为1:1，结合常数分别为 = (1.50 ± 0.10) × 10 M和 = (2.20 ± 0.16) × 10 M。拉曼光谱进一步证实了与C之间的结合亲和力。由密度泛函理论计算推导得出的与C的配合物几何结构表明，络合作用的驱动力主要归因于疏水效应和主客体π-π相互作用。疏水表面模拟表明，与C形成两亲性超分子主客体配合物，通过扫描电子显微镜测定，该配合物进一步组装成直径为0.3 - 3.5μm的微球。
