Issue 21, 2023

Conjugated figure-of-eight macrocycles derived from the anthracene photodimer: synthetic execution through intramolecular cyclization and topological manipulation through ring expansion

Abstract

Dual-cavity macrocycles with extended π-conjugation are synthetically challenging yet attractive targets, exhibiting intriguing topologies and functional properties. In this work, a series of conjugated figure-of-eight macrocycles consisting of fused aromatic subunits are facilely prepared employing intramolecular cyclizations from precursors containing an anthracene photodimer core and phenanthrene-derived side arms. In addition to functioning as an X-shaped template for cyclizations, the anthracene photodimer core also enables late-stage topological manipulations by cycloreversion, affording conjugated lemniscular macrocycles with D2 symmetry.

Graphical abstract: Conjugated figure-of-eight macrocycles derived from the anthracene photodimer: synthetic execution through intramolecular cyclization and topological manipulation through ring expansion

Supplementary files

Article information

Article type
Research Article
Submitted
22 Aug 2023
Accepted
20 Sep 2023
First published
22 Sep 2023

Org. Chem. Front., 2023,10, 5395-5401

Conjugated figure-of-eight macrocycles derived from the anthracene photodimer: synthetic execution through intramolecular cyclization and topological manipulation through ring expansion

L. Zhan, H. Xiao, J. Gao and H. Cong, Org. Chem. Front., 2023, 10, 5395 DOI: 10.1039/D3QO01351K

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