Self-assembly behavior of phenyl modified β-cyclodextrins

• Main Authors: Zhao, Yanli, Liu, Yu
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Published: 2011
• Subjects: DRNTU::Science::Biological sciences::Biochemistry
• Online Access: https://hdl.handle.net/10356/94377; http://hdl.handle.net/10220/7133
• Institution: Nanyang Technological University

The self-assembly behavior of mono(6-phenolic-6-deoxy)-β-cyclodextrin (1) both in solution and the solid state is comparatively studied by X-ray crystallography and 1H NMR spectroscopy. The results obtained show that the phenolic groups in the crystal 1 can successively penetrate into the adjacent β-cyclodextrin cavities from the secondary side to form head-to-tail linear polymeric supramolecule with a 2-fold screw axis. The self-assembly behavior also can be determined in D2O solution, giving a self-association constant of 240 mol−1⋅L. Using the present and previous structures reported for the relevant β-cyclodextrin derivatives, i.e., mono(6-anilino-6-deoxy)-β-cyclodextrin (2), mono(6-phenylselenyl-6-deoxy)-β-cyclodextrin (3), and mono(6-phenylthio-6-deoxy)-β-cyclodextrin (4), we further reveal the factors governing the formations of supramolecular assemblies.