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The Ionic Organic Cage: An Effective and Recyclable Testbed for Catalytic CO2 Transformation

Porous organic cages (POC) are a class of relatively new molecular porous materials, whose concept was raised in 2009 by Cooper’s group and has rarely been directly used in the area of organic catalysis. In this contribution, a novel ionic quasi-porous organic cage (denoted as Iq-POC), a quaternary phosphonium salt, was easily synthesized through dynamic covalent chemistry and a subsequent nucleophilic addition reaction. Iq-POC was applied as an effective nucleophilic catalyst for the cycloaddition reaction of CO2 and epoxides. Owing to the combined effect of the relatively large molecular weight (compared with PPh3+I−) and the strong polarity of Iq-POC, the molecular catalyst Iq-POC displayed favorable heterogeneous nature (i.e., insolubility) in this catalytic system. Therefore, the Iq-POC catalyst could be easily separated and recycled by simple centrifugation method, and the catalyst could be reused five times without obvious loss of activity. The molecular weight augmentation route in this study (from PPh3+I− to Iq-POC) provided us a “cage strategy” of designing separable and recyclable molecular catalysts.