Issue 81, 2019
From the journal:

Chemical Communications

Spontaneous mirror-symmetry breaking coupled to top-bottom chirality transfer: from porphyrin self-assembly to scalemic Diels–Alder adducts†

Aitor Arlegui, ORCID logo a   Bernat Soler,a   Alex Galindo,a   Oriol Arteaga,bc   Adolf Canillas, ORCID logo bc   Josep M. Ribó, ORCID logo ad   Zoubir El-Hachemi,ad   Joaquim Crusats ORCID logo *ad  and  Albert Moyano ORCID logo *a  

* Corresponding authors

a Department of Inorganic and Organic Chemistry, Universitat de Barcelona, Martí i Franquès 1, E-08028 Barcelona, Catalonia, Spain
E-mail: j.crusats@ub.edu, amoyano@ub.edu

b Department of Applied Physics, Universitat de Barcelona, Martí i Franquès 1, E-08028 Barcelona, Catalonia, Spain

c FEMAN Group, Institute of Nanoscience and Nanotechnology (IN2UB), University of Barcelona, Martí i Franquès 1, 08028 Barcelona, Catalonia, Spain

d Institute of Cosmos Science (IEEC-ICC), University of Barcelona, Martí i Franquès 1, 08028 Barcelona, Catalonia, Spain

Abstract

This report shows how the net supramolecular chirality that emerged by spontaneous mirror-symmetry breaking (SMSB) at the mesoscale level can be transferred towards asymmetric solution chemistry. The J-aggregates obtained by self-assembly of an achiral porphyrin act as chiral counteranions in an iminium-promoted Diels–Alder reaction, leading to enantiomeric imbalances in the final adducts.

Graphical abstract: Spontaneous mirror-symmetry breaking coupled to top-bottom chirality transfer: from porphyrin self-assembly to scalemic Diels–Alder adducts

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C9CC05946F
Article type
Communication
Submitted
31 Jul 2019
Accepted
16 Sep 2019
First published
25 Sep 2019

Chem. Commun., 2019,55, 12219-12222

Permissions

Request permissions

Spontaneous mirror-symmetry breaking coupled to top-bottom chirality transfer: from porphyrin self-assembly to scalemic Diels–Alder adducts

A. Arlegui, B. Soler, A. Galindo, O. Arteaga, A. Canillas, J. M. Ribó, Z. El-Hachemi, J. Crusats and A. Moyano, Chem. Commun., 2019, 55, 12219 DOI: 10.1039/C9CC05946F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements