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Self‐Assembly of Di‐N‐Heterocyclic Carbene‐Gold‐Adorned Corannulenes on C 60
Author(s) -
Mejuto Carmen,
Escobar Luis,
GuisadoBarrios Gregorio,
Ballester Pablo,
Gusev Dmitry,
Peris Eduardo
Publication year - 2017
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.201701728
Subject(s) - corannulene , chemistry , fullerene , toluene , deprotonation , carbene , molecule , titration , stoichiometry , crystallography , computational chemistry , inorganic chemistry , organic chemistry , ion , catalysis
The deprotonation of a corannulene‐based bisazolium salt allowed the preparation of a corannulene‐based NHC di‐Au I complex. The prepared di‐Au I ‐complex was tested in the recognition of fullerene‐C 60 , demonstrating good binding affinity in toluene solution, and producing a host–guest complex with 3:1 stoichiometry, as evidenced by a combination of NMR spectroscopy and ITC titrations. The experimental results are fully supported by DFT calculations. The binding of C 60 with the di‐Au I complex in toluene solution is enthalpically and entropically favoured. Remarkably, the entropic term is the dominant parameter in the binding process. The good complementarity that exists between the concave shape of the corannulene‐di‐gold complex and the convex surface of the fullerene, together with the presence of t Bu groups and the AuCl fragment are key factors for the measured high affinity between host and guest. The obtained results indicate that fullerene may be acting as a template for the formation of a self‐assembled aggregate involving up to three molecules of the di‐Au I complex.