Premium
[2]Catenane Synthesis via Covalent Templating
Author(s) -
Pilon Simone,
Ingemann Jørgensen Steen,
Maarseveen Jan H.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004925
Subject(s) - catenane , rotaxane , covalent bond , supramolecular chemistry , chemistry , dynamic covalent chemistry , molecule , cleavage (geology) , linkage (software) , stereochemistry , combinatorial chemistry , nanotechnology , materials science , organic chemistry , biochemistry , fracture (geology) , composite material , gene
After earlier unsuccessful attempts, this work reports the application of covalent templating for the synthesis of mechanically interlocked molecules (MiMs) bearing no supramolecular recognition sites. Two linear strands were covalently connected in a perpendicular fashion by a central ketal linkage. After subsequent attachment of the first strand to a template via temporary benzylic linkages, the second was linked to the template in a backfolding macrocyclization. The resulting pseudo[1]rotaxane structure was successfully converted to a [2]catenane via a second macrocyclization and cleavage of the ketal and temporary linkages.