Template Synthesis of Three‐Dimensional Hexakisimidazolium Cages

A procedure for the synthesis of three‐dimensional hexakisimidazolium cage compounds has been developed. The reaction of the trigonal trisimidazolium salts H3L(PF6)3, decorated with three N‐olefinic pendants, and silver oxide yielded trinuclear trisilver(I) hexacarbene molecular cylinders of the typ...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-04, Vol.57 (18), p.5161-5165
Main Authors: Sun, Li‐Ying, Sinha, Narayan, Yan, Tao, Wang, Yi‐Shou, Tan, Tristan T. Y., Yu, Le, Han, Ying‐Feng, Hahn, F. Ekkehardt
Format: Article
Language:English
Subjects:
Cage compounds
Cages
carbenes
Chemical synthesis
Cycloaddition
Cyclobutane
Cylinders
Irradiation
Ligands
Metal ions
Molecular chains
photochemical cycloaddition
Salts
Silver
supramolecular chemistry
template synthesis
Ultraviolet radiation
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Summary:A procedure for the synthesis of three‐dimensional hexakisimidazolium cage compounds has been developed. The reaction of the trigonal trisimidazolium salts H3L(PF6)3, decorated with three N‐olefinic pendants, and silver oxide yielded trinuclear trisilver(I) hexacarbene molecular cylinders of the type [Ag3L2]3+ with the olefinic pendants from the two different tricarbene ligands arranged in three pairs. Subsequent UV irradiation gave three cyclobutane links between the two tris‐NHC ligands in three [2+2] cycloaddition reactions, thereby generating a three‐dimensional hexakis‐NHC ligand. Removal of the metal ions resulted in the formation of three‐dimensional hexakisimidazolium cages with a large internal cavity. All good things come in threes: An efficient template synthesis has been developed for the preparation of three‐dimensional hexakisimidazolium cage compounds starting from trigonal trisimidazolium salts decorated with three N‐olefinic pendants and silver ions as metal templates.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201713240