Sulfoxide-Induced Homochiral Folding of o-OPEs by AgI Templating: Structure and Chiroptical Properties
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Resa, Sandra; Miguel Álvarez, Delia; Guisán-Ceinos, Santiago; Mazzeo, Giuseppe; Choquesillo Lazarte, Duane; Abbate, Sergio; Crovetto González, Luis; Cárdenas, Diego J.; Carreño, M. Carmen; Ribagorda, María; Longhi, Giovanna; Mota Ávila, Antonio José; Álvarez Cienfuegos Rodríguez, Luis; Cuerva Carvajal, Juan ManuelEditorial
Wiley
Materia
Supramolecular Chemistry Chiroptical properties Helical structures Host-guest systems Nanostructures
Date
2018-01-24Referencia bibliográfica
Resa, S.; et al. Sulfoxide-Induced Homochiral Folding of o-OPEs by AgI Templating: Structure and Chiroptical Properties. Chemistry a European Journal [postprint], 2018. [http://hdl.handle.net/10481/49265]
Sponsorship
We thank MINECO (FEDER funded grant CTQ2014-53598-R). Computing Center CINECA, Bologna, Italy, Regione Lombardia for the LISA Grant No. “ChiPhyto: HPL13POZE1” and the “Centro de Supercomputación de la UGR” (UGRGRID) are acknowledged for access to computational facilities. Sandra Resa thanks the MECD for a FPU fellowship.Abstract
A new family of homochiral silver complexes based on carbophilic interactions with ortho-phenyleneethynylene (o-OPE)
scaffolds containing up to two silver atoms is described. These
compounds represent a unique class of complexes with chirality at the metal. Chiral induction is based on the inclusion of chiral sulfoxides which allow an efficient transfer of chirality to the helically
folded o-OPE, leading to CPL and VCD active compounds. In the presence of AgI cation carbophilic interactions dominate, promoting helical structures with a defined helicity. This is one of the very
scarce examples of the use of such interactions in the attractive field
of abiotic foldamers. The switching event has been extensively studied using different chiroptical techniques including CD, CPL and VCD, also representing one of the few CPL switches described in
literature.