Homochiral Metal-Organic Framework with Interconnected Double Helical Channels Constructed by Figure-Eight Lig-ands

The development of a new molecular building block for the construction of elaborated molecular assemblies extends the chemical space for materials exploration. While representative organic components for the design of chiral porous materials adopt C1- and C2-symmetries, the use of more symmetric components has been underexplored due to syn-thetic limitations. Herein, we synthesized a homochiral metal-organic framework (MOF), CBBCMOF, using a readily available figure-eight D2-symmetric macrocycle, namely cyclobisbiphenylenecarbonyl (CBBC), as a ligand. The crystal structure of CBBCMOF shows a quasi-honeycomb framework with interconnected double helical channels, whose pore size exceeds 10 Å. Owing to the large inner cavity, CBBCMOF encapsulated various guest molecules, including aromatic hydrocarbons, alcohols, and dyes. Treatment of racemic 1,1'-bi-2-naphthol (BINOL) with CBBCMOF resulted in the en-antioselective encapsulation with the highest enantiomeric excess to date. Furthermore, CBBCMOF is persistent in vari-ous solvents and thus functions as stationary phases of chromatography to separate the enantiomers of medium-sized chiral molecules.