Issue 9, 2016
From the journal:

Chemical Science

Stapled helical o-OPE foldamers as new circularly polarized luminescence emitters based on carbophilic interactions with Ag(i)-sensitivity†‡

Sara P. Morcillo,a   Delia Miguel,*b   Luis Álvarez de Cienfuegos,b   José Justicia,b   Sergio Abbate,c   Ettore Castiglioni,c   Christophe Bour,a   María Ribagorda,d   Diego J. Cárdenas,d   José Manuel Paredes,e   Luis Crovetto,e   Duane Choquesillo-Lazarte,f   Antonio J. Mota,g   M. Carmen Carreño,d   Giovanna Longhi*c  and  Juan M. Cuerva*b  

* Corresponding authors

a Institut de Chimie Moléculaire et des Matériaux d'Orsay, CNRS UMR 8182, Univ. Paris-Sud Université Paris-Saclay bâtiment 420, 91405 Orsay cedex, France

b Department of Organic Chemistry, University of Granada (UGR), C. U. Fuentenueva, 18071 Granada, Spain
E-mail: jmcuerva@ugr.es, dmalvarez@ugr.es

c Dipartimento di Medicina Molecolare e Traslazionale, Università di Brescia, Viale Europa 11, 25123 Brescia, Italy
E-mail: giovanna.longhi@unibs.it

d Departamento de Química Orgánica, Universidad Autónoma de Madrid, c/Francisco Tomás y Valiente n° 7, Cantoblanco, 28049 Madrid, Spain

e Department of Physical Chemistry, Faculty of Pharmacy, UGR, Cartuja Campus, 18071 Granada, Spain

f Laboratorio de Estudios Cristalográficos, Instituto Andaluz de Ciencias de la Tierra (CSIC-UGR), 18100 Armilla, Granada, Spain

g Department of Inorganic Chemistry, UGR, C. U. Fuentenueva, 18071 Granada, Spain

Abstract

ortho-Oligo(phenylene)ethynylenes (o-OPEs) stapled with enantiopure 2,3-dihydroxybutane diethers have highly intense circular dichroism (CD) spectra and excellent circular polarized luminescence (CPL) responses (glum values up to 1.1 × 10−2), which are consistent with homochiral helically folded structures. In the presence of Ag(I), a change in the CPL emission is observed, representing the first example of CPL active small organic molecular emitters, which can be modulated by carbophilic interactions in a reversible manner.

Graphical abstract: Stapled helical o-OPE foldamers as new circularly polarized luminescence emitters based on carbophilic interactions with Ag(i)-sensitivity

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DOI
https://doi.org/10.1039/C6SC01808D
Article type
Edge Article
Submitted
25 Apr 2016
Accepted
16 May 2016
First published
17 May 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 5663-5670

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Stapled helical o-OPE foldamers as new circularly polarized luminescence emitters based on carbophilic interactions with Ag(I)-sensitivity

S. P. Morcillo, D. Miguel, L. Álvarez de Cienfuegos, J. Justicia, S. Abbate, E. Castiglioni, C. Bour, M. Ribagorda, D. J. Cárdenas, J. M. Paredes, L. Crovetto, D. Choquesillo-Lazarte, A. J. Mota, M. C. Carreño, G. Longhi and J. M. Cuerva, Chem. Sci., 2016, 7, 5663 DOI: 10.1039/C6SC01808D

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