A self-complementary macrocycle by a dual interaction system

Yuta Sawanaka, Masahiro Yamashina (), Hiroyoshi Ohtsu and Shinji Toyota ()
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Yuta Sawanaka: Tokyo Institute of Technology
Masahiro Yamashina: Tokyo Institute of Technology
Hiroyoshi Ohtsu: Tokyo Institute of Technology
Shinji Toyota: Tokyo Institute of Technology

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract Self-complementary assembly is one of the most promising phenomena for the formation of discrete assemblies, e.g., proteins and capsids. However, self-complementary assembly based on multiple host-guest systems has been scarcely reported due to the difficulty in controlling each assembly. Herein, we report a dual interaction system in which the key assembly direction is well regulated by both π-π stacking and hydrogen bonding to construct a self-complementary macrocycle. Continuous host-guest behavior of anthracene-based molecular tweezers during crystallization leads to successful construction of a cyclic hexamer, which is reminiscent of Kekulé’s monkey model. Furthermore, the cyclic hexamer in a tight and triple-layered fashion shows hierarchical assembly into cuboctahedron and rhombohedral assemblies in the presence of trifluoroacetic acid. Our findings would be potentially one of metal-free strategies for constructing anthracene-based supramolecular assemblies with higher-order structure.

Date: 2022
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DOI: 10.1038/s41467-022-33357-y

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