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Concentration‐Dependent Self‐Assembly of an Unusually Large Hexameric Hydrogen‐Bonded Molecular Cage
Author(s) -
Merget Severin,
Catti Lorenzo,
Zev Shani,
Major Dan T.,
Trapp Nils,
Tiefenbacher Konrad
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.202005046
Subject(s) - hydrogen bond , monomer , cage , self assembly , covalent bond , supramolecular chemistry , intermolecular force , chemistry , amide , crystallography , fullerene , molecule , crystal structure , organic chemistry , polymer , mathematics , combinatorics
The sizes of available self‐assembled hydrogen‐bond‐based supramolecular capsules and cages are rather limited. The largest systems have volumes of approximately 1400–2300 Å 3 . Herein, we report a large, hexameric cage based on intermolecular amide–amide dimerization. The unusual structure with openings, reminiscent of covalently linked cages, is held together by 24 hydrogen bonds. With a diameter of 2.3 nm and a cavity volume of ∼2800 Å 3 , the assembly is larger than any previously known capsule/cage structure relying exclusively on hydrogen bonds. The self‐assembly process in chlorinated, organic solvents was found to be strongly concentration dependent, with the monomeric form prevailing at low concentrations. Additionally, the formation of host–guest complexes with fullerenes (C 60 and C 70 ) was observed.