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

doi:10.1002/ejoc.201700305

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

Bio-Organic Chemistry

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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 language	English
Article number	21
Pages (from-to)	3107-3113
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	21
DOIs	https://doi.org/10.1002/ejoc.201700305
Publication status	Published - 8 Jun 2017

Keywords

Click chemistry
Cycloaddition
Polycycles
Reactive chain stoppers
Rotaxanes

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10.1002/ejoc.201700305

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title = "A dibenzoazacyclooctyne as a reactive chain stopper for [2]rotaxanes",

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.",

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AU - Hou, Z.-Y.

AU - Yeniad, B.

AU - van Guyse, J.

AU - Woisel, P.

AU - Mullen, K.M.

AU - Rutjes, F.P J.T.

AU - van Hest, J.C.M.

AU - Hoogenboom, R.

PY - 2017/6/8

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AB - 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.

KW - Click chemistry

KW - Cycloaddition

KW - Polycycles

KW - Reactive chain stoppers

KW - Rotaxanes

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M3 - Article

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JF - European Journal of Organic Chemistry

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M1 - 21

ER -

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

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Keywords

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