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Spontaneous Resolution of an Electron‐Deficient Tetrahedral Fe 4 L 4 cage
Author(s) -
Bonakdarzadeh Pia,
Pan Fangfang,
Kalenius Elina,
Jurček Ondřej,
Rissanen Kari
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507295
Subject(s) - supramolecular chemistry , crystallization , crystallography , cage , chemistry , tetrahedron , crystal (programming language) , crystal structure , resolution (logic) , ligand (biochemistry) , nuclear magnetic resonance spectroscopy , enantiomer , spectroscopy , stereochemistry , physics , organic chemistry , combinatorics , artificial intelligence , computer science , programming language , quantum mechanics , biochemistry , receptor , mathematics
A highly electron‐deficient C 3 ‐symmetric tris(bipyridyl) ligand was prepared in four steps and used for the coordination of Fe(OTf) 2 , thereby resulting in the homochiral assembly of a new family of robust tetrahedral M 4 L 4 cages. This homochiral T‐symmetric cage containing a relatively large cavity of 330 Å 3 is capable of encapsulating an anionic guest, as was determined by mass spectrometry, 19 F NMR spectroscopy, and finally shown from its crystal structure. Moreover, crystallization of the cage from CH 3 CN led to crystals containing both (ΔΔΔΔ and ΛΛΛΛ) enantiomers, while crystallization from CH 3 OH resulted in crystals containing only the right‐handed (ΔΔΔΔ) cage. The difference in the crystal packing of the two crystal structures is discussed and a feasible explanation for the unique phenomenon among supramolecular cages—spontaneous resolution—is given.