Linker-Directed Assembly of Twisted ortho-Phenylene-Based Macrocycles

o-Phenylene tetramers have been coassembled with linkers into macrocycles through imine condensation. Variation of linker connectivity and length allows both [1 + 1] and [2 + 2] macrocycles to be obtained, complementing (previously reported) [3 + 3] macrocycles. For the [1 + 1] macrocycles, linker l...

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Bibliographic Details
Published in:Organic letters 2018-06, Vol.20 (11), p.3327-3331
Main Authors: Kinney, Zacharias J, Hartley, C. Scott
Format: Article
Language:English
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Summary:o-Phenylene tetramers have been coassembled with linkers into macrocycles through imine condensation. Variation of linker connectivity and length allows both [1 + 1] and [2 + 2] macrocycles to be obtained, complementing (previously reported) [3 + 3] macrocycles. For the [1 + 1] macrocycles, linker length has a clear effect on o-phenylene geometry and macrocycle stability. For the [2 + 2] macrocycles, both homo- and heterochiral configurations are observed, suggesting limited communication of helix handedness in these systems.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01237