Porous molecular crystals are distinct from other classes of porous materials in that they are built from discrete molecules, rather than extended polymeric structures. This structural feature translates into the superior processability in solution and vapor phase and easy synthetic access. However, porous molecular crystals are rare and fundamentally unusual, as most molecules tend to closely pack in the solid state. During the past four years, we have discovered two classes of small organic molecules that assemble into porous crystalline structures. The first is based on rigid and extensively fluorinated aromatic pyrazoles and tetrazoles, which form extrinsically porous structures through a combiantion of hydrogen bonding betwene their termini and [π…π] stacking between the electron-poor tetrafluorobenzenes and electron-rich five membered heteroaromatic rings. These porous materials have proven to be useful adsorbents for fluorinated pollutants and inhalation anesthetics, and also show aggregation-induced emission in the dissolved state. The second class is based on shape-persistent macrocycles called cyclobenzoins, which can be prepared from rigid aromatic dialdehydes in a single step. These intrinsically porous molecular crystals have relatively low surface areas, but are promising as progenitors of a whole area of new potentially more porous macrocycles. This presentation, given in honor of Mircea's ACS Award in Pure Chemistry, will summarize our work on both of these classes of materials.

Porous molecular crystals based on fluorinated aromatics and cyclobenzoins

255th National Meeting (2018)

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