3 years ago

Synthesis and Bowl-in-Bowl Assembly of a Geodesic Phenylene Bowl

Synthesis and Bowl-in-Bowl Assembly of a Geodesic Phenylene Bowl
Hiroyuki Isobe, Koki Ikemoto, Sota Sato, Ryo Kobayashi
A phenylene multiring with a corannulenoidal skeleton was synthesized. Geodesic constraints over 20 phenylene panels resulted in its nanometer-sized, bowl-shaped molecular structure, which was unequivocally revealed by crystallographic analysis. The crystal structure also showed the presence of a bowl-in-bowl dimeric assembly, which was driven by entropic factors in solution. Shape sorting: Geodesic constraints arising from the coupling of trigonal planar phenylenes into a pentagon surrounded by five hexagons resulted in a nanometer-sized bowl-shaped molecule. Concave–convex molecular recognition resulted in the molecules assembling in a bowl-in-bowl fashion. The shape recognition was driven by an entropy gain for the assembly of the large 120 π-systems.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702063

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