Synthesis of ExnBox cyclophanes

Jonathan C. Barnes, Michal Juríček, Nicolaas A. Vermeulen, Edward J. Dale, J Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

51 Scopus citations

Abstract

A rapid and efficient synthesis of the extended bipyridinium-based class of cyclophanes - that is, ExnBox4+ (n = 0-3), where n is the number of p-phenylene rings inserted between the pyridinium rings - is demonstrated, resulting in much higher yields of products along with a reduced output of oligomeric byproducts. Although each cyclophane can be synthesized readily without the use of a precise stoichiometric amount of template, ExBox4+ can be prepared in 66% yield (following crystallization) using six equivalents of pyrene in a template-directed protocol. This new methodology has been employed to synthesize, in modest yield, a nearly 2.5 nm long cyclophane consisting of 12 aromatic rings.

Original languageEnglish (US)
Pages (from-to)11962-11969
Number of pages8
JournalJournal of Organic Chemistry
Volume78
Issue number23
DOIs
StatePublished - Dec 6 2013

ASJC Scopus subject areas

  • Organic Chemistry

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