A dibenzoazacyclooctyne as a reactive chain stopper for [2]rotaxanes

Z.-Y. Hou, B. Yeniad, J. van Guyse, P. Woisel, K.M. Mullen, F.P J.T. Rutjes, J.C.M. van Hest, R. Hoogenboom

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

A strained dibenzoazacyclooctyne (DIBAC) derivative was introduced for the preparation of a rotaxane by strain-promoted azide-alkyne cycloaddition (SPAAC), also referred to as a copper-free click reaction. The DIBAC can efficiently act as a bulky reactive chain stopper to transform a pseudorotaxane architecture consisting of a diazo-functionalized dialkoxy-naphthalene guest and a tetracationic cyclobis(paraquat-p-phenylene) (CBPQT(4+)) host into the corresponding [2]rotaxane. Furthermore, the use of the DIBAC is demonstrated to be limited to short rigid macrocycles, as it is unable to act as stopper for a rotaxane featuring a larger crown ether macrocyclic host.
Original languageEnglish
Article number21
Pages (from-to)3107-3113
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number21
DOIs
Publication statusPublished - 8 Jun 2017

Keywords

  • Click chemistry
  • Cycloaddition
  • Polycycles
  • Reactive chain stoppers
  • Rotaxanes

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    Hou, Z-Y., Yeniad, B., van Guyse, J., Woisel, P., Mullen, K. M., Rutjes, F. P. J. T., van Hest, J. C. M., & Hoogenboom, R. (2017). A dibenzoazacyclooctyne as a reactive chain stopper for [2]rotaxanes. European Journal of Organic Chemistry, 2017(21), 3107-3113 . [21]. https://doi.org/10.1002/ejoc.201700305