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 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.
- Click chemistry
- Reactive chain stoppers
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 rotaxanes. European Journal of Organic Chemistry, 2017(21), 3107-3113 . . https://doi.org/10.1002/ejoc.201700305