Optically active Ag(I): o-OPE helicates using a single homochiral sulfoxide as chiral inducer

Sandra Resa; Pablo Reiné; Luis Álvarez de Cienfuegos; Santiago Guisán-Ceinos; María Ribagorda; Giovanna Longhi; Giuseppe Mazzeo; Sergio Abbate; Antonio J. Mota; Delia Miguel; Juan M. Cuerva

doi:10.1039/C9OB01573F

Optically active Ag(i): o-OPE helicates using a single homochiral sulfoxide as chiral inducer†

Sandra Resa,^a Pablo Reiné,^a Luis Álvarez de Cienfuegos,

^a Santiago Guisán-Ceinos,^b María Ribagorda,

^b Giovanna Longhi,

^c Giuseppe Mazzeo,

^c Sergio Abbate,

^c Antonio J. Mota,

^d Delia Miguel

*^e and Juan M. Cuerva

*^a

Author affiliations

* Corresponding authors

^a Department of Organic Chemistry, Unidad de Excelencia de Química (UEQ), University of Granada, C.U. Fuentenueva, Granada, Spain
E-mail: jmcuerva@ugr.es

^b Department of Organic Chemistry, C.U. Cantoblanco, Universidad Autónoma de Madrid, Spain

^c Dipartimento di Medicina Molecolare e Traslazionale, Universitá di Brescia, Viale Europa 11, Brescia, Italy

^d Department of Inorganic Chemistry, UEQ, University of Granada, C.U. Fuentenueva, Granada, Spain

^e Department of Physical Chemistry, UEQ, University of Granada, C.U. Cartuja, Granada, Spain
E-mail: dmalvarez@ugr.es

Abstract

In this work we describe the ability of a simple enantiopure sulfoxide group to promote folding of oligo ortho-phenylene ethynylenes (o-OPEs) with one helical sense. A family of foldamers with up to seven triple bonds was synthesized and fully characterized. Moreover, changes in structure and chiroptical properties caused by Ag(I) coordination have been studied by NMR, UV, VCD and ECD measurements. Quantum mechanical DFT calculations support experimental results.

This article is part of the themed collection: Supramolecular chemistry in OBC

Organic & Biomolecular Chemistry

Optically active Ag(i): o-OPE helicates using a single homochiral sulfoxide as chiral inducer†

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Optically active Ag(I): o-OPE helicates using a single homochiral sulfoxide as chiral inducer

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