A Dibenzoazacyclooctyne as a Reactive Chain Stopper for [2]Rotaxanes

作者：Hou Zhan Yao; Yeniad Bahar; Van Guyse Joachim; Woisel Patrice; Mullen Kathleen M; Rutjes Floris P J T; van Hest Jan C M; Hoogenboom Richard

来源：European Journal of Organic Chemistry, 2017, 2017(21): 3107-3113.

DOI：10.1002/ejoc.201700305

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

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.

• 出版日期2017-6-8