A Strategy Utilizing a Recyclable Macrocycle Transporter for the Efficient Synthesis of a Triazolium‐Based [2]Rotaxane | Zendy

Chao Sovy | Zendy; Romuald Camille | Zendy; FournelMarotte Karine | Zendy; Clavel Caroline | Zendy; Coutrot Frédéric | Zendy

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A Strategy Utilizing a Recyclable Macrocycle Transporter for the Efficient Synthesis of a Triazolium‐Based [2]Rotaxane

Author(s) -

Chao Sovy,

Romuald Camille,

FournelMarotte Karine,

Clavel Caroline,

Coutrot Frédéric

Publication year - 2014

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201403765

Subject(s) - rotaxane , moiety , chemistry , slippage , sequence (biology) , transporter , yield (engineering) , stereochemistry , combinatorial chemistry , materials science , molecule , organic chemistry , biochemistry , supramolecular chemistry , gene , composite material , metallurgy

A general synthesis of triazolium‐containing [2]rotaxanes, which could not be accessed by other methods, is reported. It is based on a sequential strategy starting from a well‐designed macrocycle transporter which contains a template for dibenzo‐24‐crown‐8 and a N ‐hydroxysuccinimide (NHS) moiety. The sequence is: 1) synthesis by slippage of a [2]rotaxane building‐block; 2) its elongation at its NHS end; 3) the delivery of the macrocycle to the elongated part of the axle by an induced translational motion; 4) the contraction process to yield the targeted [2]rotaxane and recycle the initial transporter.

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