A tetrahedral molecular cage with a responsive vertex

Dynamic covalent chemistry (DCC) is a widely used method for the self-assembly of three-dimensional molecular architectures. The orthogonality of dynamic reactions is emerging as a versatile strategy for controlling product distributions in DCC, yet the application of this approach to the synthesis...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2019-08, Vol.1 (29), p.743-748
Main Authors: Pattillo, Christopher C, Moore, Jeffrey S
Format: Article
Language:English
Subjects:
Alkynes
Cages
Chemical synthesis
Metathesis
Organic chemistry
Orthogonality
Self-assembly
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Summary:Dynamic covalent chemistry (DCC) is a widely used method for the self-assembly of three-dimensional molecular architectures. The orthogonality of dynamic reactions is emerging as a versatile strategy for controlling product distributions in DCC, yet the application of this approach to the synthesis of 3D organic molecular cages is limited. We report the first system which employs the orthogonality of alkyne metathesis and dynamic imine exchange to prepare a molecular cage with a reversibly removable vertex. This study demonstrates the rational and controlled application of chemical orthogonality in DCC to prepare organic cages of expanded functionality which respond to chemical stimuli. The first system to combine the orthogonality of alkyne metathesis and dynamic imine exchange is reported for the preparation of a molecular cage with a reversibly removable vertex.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc02047k