4 years ago

A Molecular Propeller with Three Nanohoop Blades: Synthesis, Characterization, and Solid-State Packing

A Molecular Propeller with Three Nanohoop Blades: Synthesis, Characterization, and Solid-State Packing
Penghao Li, Lev N. Zakharov, Ramesh Jasti
Nanoscale carbon-rich molecular architectures are not only aesthetically appealing but also of practical importance for energy and biomedical technologies. Herein, we report the synthesis of cyclic-oligophenylene-based nanopropeller 1 by using an efficient synthon strategy involving sequential intramolecular bisboronate homocoupling and reductive aromatization by H2SnCl4. The nanopropeller molecules pack into a layered hexagonal lattice featuring long-ranged nano-sized channels and a total guest-accessible volume of 48 %, as revealed by X-ray diffraction studies. We suggest that such a solid-state arrangement is determined by the interplay between the propeller architecture and the intermolecular van der Waals interactions. Nanohoops propel ahead: A triptycene-based molecular propeller with three nanohoop blades was synthesized by a three-fold intramolecular bisboronate homocoupling and subsequent reductive aromatization. Such nanopropeller molecules pack into a lamellar hexagonal structure with 11 Å-diameter channels that run perpendicularly to the layers.

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

DOI: 10.1002/anie.201700935

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