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Article Dans Une Revue European Journal of Organic Chemistry Année : 2017

Dibenzo-azacyclooctyne as Reactive Chain Stopper for [2]Rotaxanes

Résumé

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 dialkoxynaphthalene guest and a tetracationic cyclobis(paraquat-p-phenylene) (CBPQT4+) 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.

Dates et versions

hal-04547917 , version 1 (16-04-2024)

Identifiants

Citer

Zhanyao Hou, Bahar Yeniad, Joachim van Guyse, Patrice Woisel, Kathleen Mullen, et al.. Dibenzo-azacyclooctyne as Reactive Chain Stopper for [2]Rotaxanes. European Journal of Organic Chemistry, 2017, European Journal of Organic Chemistry, 2017, pp.3107-3113. ⟨10.1002/ejoc.201700305⟩. ⟨hal-04547917⟩
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