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Asararenes—A Family of Large Aromatic Macrocycles

Authors

  • Dr. Severin T. Schneebeli,

    1. Center for the Chemistry of Integrated Systems and Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-311 (USA), Fax: (+1) 847-491-1009
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    • These authors contributed equally to this work.

  • Chuyang Cheng,

    1. Center for the Chemistry of Integrated Systems and Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-311 (USA), Fax: (+1) 847-491-1009
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    • These authors contributed equally to this work.

  • Dr. Karel J. Hartlieb,

    1. Center for the Chemistry of Integrated Systems and Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-311 (USA), Fax: (+1) 847-491-1009
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  • Nathan L. Strutt,

    1. Center for the Chemistry of Integrated Systems and Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-311 (USA), Fax: (+1) 847-491-1009
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  • Dr. Amy A. Sarjeant,

    1. Center for the Chemistry of Integrated Systems and Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-311 (USA), Fax: (+1) 847-491-1009
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  • Dr. Charlotte L. Stern,

    1. Center for the Chemistry of Integrated Systems and Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-311 (USA), Fax: (+1) 847-491-1009
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  • Prof. J. Fraser Stoddart

    Corresponding author
    1. Center for the Chemistry of Integrated Systems and Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-311 (USA), Fax: (+1) 847-491-1009
    • Center for the Chemistry of Integrated Systems and Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-311 (USA), Fax: (+1) 847-491-1009
    Search for more papers by this author

Abstract

We announce the establishment of a new family of macrocycles—the asararenes, which are based on para-methylene linked “asarol methyl ether” (1,2,4,5-tetramethoxybenzene) units. Macrocycles with 6–12 aromatic units have been synthesized and isolated in a single step from asarol methyl ether and paraformaldehyde. Even larger rings, with up to 15 asarol methyl ether units, have been observed by high-resolution mass spectrometry. Single-crystal X-ray structures of asar[6]-, asar[7]-, asar[8]-, asar[9]-, asar[10]- and asar[11]arene highlight the diverse structural features of this family of macrocycles. While the cavities of the asar[6–8]arene macrocycles are mostly filled with methoxyl groups, the asar[9]- and asar[10]arene rings contain accessible cavities and self-assemble into infinite channels filled with solvent molecules in the solid state. These solid-state structures highlight the potential of this family of macrocycles for a wide range of potential applications.

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