Trefoil-Shaped Porous Nanographenes Bearing a Tribenzotriquinacene Core by Three-fold Scholl Macrocyclization.

Porous curved polycyclic aromatic compounds 6 and 14 bearing a tribenzotriquinacene (TBTQ) core encircled by an m,p,p,m,m,p,p,m,m,p,p,m-cyclododecaphenylene belt were synthesized and characterized by NMR spectroscopy and mass spectrometry. These trefoil hydrocarbon macrocycles were constructed in high yield using an intramolecular three-fold Scholl macrocyclization. X-ray crystal analysis of 14 demonstrated a large wizard-hat-shaped structure with three pores (radii 2.9-3.0 Å). The π-stacking aggregation of the hexa-n-dodecyloxy derivative 6 a and the chloride anion binding properties of 14 were studied by NMR spectroscopy. Such stacking and anion binding properties were much weaker in the singly 11 and doubly macrocyclized products 12.