Chiral Overpass Induction in Dynamic Helical Polymers Bearing Pendant Groups with Two Chiral Centers
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Title: | Chiral Overpass Induction in Dynamic Helical Polymers Bearing Pendant Groups with Two Chiral Centers |
Author: | Suárez Picado, Esteban Quiñoá Cabana, Emilio Riguera Vega, Ricardo Freire Iribarne, Félix Manuel |
Affiliation: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
Subject: | Cation–π interactions | Chirality | Circular dichroism | Helical polymers | Poly(phenylacetylene) | |
Date of Issue: | 2020 |
Publisher: | Wiley |
Citation: | E. Suárez-Picado, E. Quiñoá, R. Riguera, F. Freire, Angew. Chem. Int. Ed. 2020, 59, 4537 |
Abstract: | The dynamic behavior of helical polymers bearing pendant groups with two chiral centers was studied. Controlled conformational changes at the chiral units placed either closer to or further away from the main chain promote different helical structures. Although the first residue is usually responsible for determining a specific helicity (P or M), we now found that the second chiral center is also able to induce a preferred helical sense when it is located closer in space to the main chain, thereby cancelling the order from the first chiral moiety. This result was achieved through proper coordination with a metal cation. As proof of concept, poly(phenylacetylene)s (PPAs) that bear one and two chiral amino acid units of different sizes and configuration combinations (l/d‐alanine and l/d‐phenylalanine) as pendants were evaluated. In total, ten polymers were studied. This constitutes the first report of axial control from a remote stereocenter in polymers bearing complex chiral pendants |
Description: | This is the peer reviewed version of the following article: E. Suárez-Picado, E. Quiñoá, R. Riguera, F. Freire, Angew. Chem. Int. Ed. 2020, 59, 4537, which has been published in final form at https://doi.org/10.1002/anie.201915213. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions |
Publisher version: | https://doi.org/10.1002/anie.201915213 |
URI: | http://hdl.handle.net/10347/23377 |
DOI: | 10.1002/anie.201915213 |
ISSN: | 1433-7851 |
E-ISSN: | 1521-3773 |
Rights: | © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for self-archiving |
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