In recent years, design and synthesis of well-defined, two- or three-dimensional molecular architectures through highly efficient dynamic covalent chemistry have attracted great attention. However, utilizing alkyne metatheis to achieve 3-D molecular cage synthesis has not been explored. In this presentation, we will show the successful synthesis of 3-D carbazole-based cage molecules (in one step starting from monomers in good yields) by using our newly developed multidentate alkyne metathesis catalyst. MALDI-MS, 1H NMR, gCOSY and ROESY experiments were conducted to investigate the structure of the obtained tetrameric molecular cage. NMR titration experiments showed the capability of the obtained cage compound to bind fullerenes, with higher association constant observed for C70 than for C60, which is also consistent with theoretical calculations.

Highly efficient construction of a shape-persistent molecular cage through alkyne metathesis and study on its fullerene binding behavior

242nd National Meeting (2011)

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