Postmodification of the electronic properties by addition of π-stacking additives in N-heterocyclic carbene complexes with extended polyaromatic systems

Inorganic Chemistry
Hugo ValdésEduardo Peris

Abstract

A series of iridium complexes containing phenanthro[4,5-abc]phenazino[11,12-d]imidazol-2-ylidene and acetonaphtho[1,2-b]quinoxaline[11,12-d]imidazol-2-ylidene ligands have been obtained and fully characterized. These complexes display highly extended polyaromatic systems attached to the backbone of the N-heterocyclic carbene. The presence of this extended polyaromatic system makes the electron-donating character of these ligands sensitive to the presence of π-stacking additives, such as pyrene and hexafluorobenzene. The computational studies predict that the addition of pyrene affords an increase of the electron-donating character of the polyaromatic ligand (Tolman electronic parameter (TEP) decreases), while the addition of hexafluorobenzene has the opposite effect (TEP increases). This prediction is experimentally corroborated by IR spectroscopy, by measuring the shift of the CO stretching bands of a series of IrCl(NHC)(CO)2 complexes, where NHC is the N-heterocyclic carbene ligand with the polyaromatic system. Finally, the energy of the π-stacking interaction of one of the key Ir(I) complexes with pyrene and hexafluorobenzene has been estimated by using the Benesi-Hildebrand treatment, based on the δ-shifts observed by (1)H ...Continue Reading

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Citations

Feb 24, 2016·Inorganic Chemistry·Dani SetiawanDieter Cremer
Apr 13, 2017·Chemistry : a European Journal·Daniel NuevoEduardo Peris
Mar 30, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Dieter Cremer, Elfi Kraka
Apr 12, 2016·Chemical Communications : Chem Comm·Eduardo Peris
Aug 18, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·S IbañezE Peris
May 22, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Haoyu NiuSimon Aldridge
Apr 6, 2019·Chemistry : a European Journal·Pilar BallestinPedro J Pérez

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