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      Diastereomeric multi‐chiral pendant groups: Their key role in stimuli‐responsive polymeric responses

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          Abstract

          Chiral information transmission in helical polymers bearing multi‐chiral pendant groups is usually determined by the absolute configuration of the first chiral center. The second chiral residue usually has low‐to‐null influence in the macromolecular handedness of the polymer, due to its remote position respect to the polyene main chain. Here, we demonstrate how the stimuli responsive properties of diastereomeric polymers, obtained by changing the absolute configuration of the second chiral center, are different due to the unlike properties of diastereoisomers.

          Abstract

          Diastereomeric poly(phenylacetylene) containing ( S)‐valine and ( R)/( S) α‐methoxy‐α‐phenylacetic acid as pendants exhibit a different response to external stimuli, such as solvent polarity.

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          Most cited references54

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          Helical polymers: synthesis, structures, and functions.

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            Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions.

            In this review, we describe the recent advances in supramolecular helical assemblies formed from chiral and achiral small molecules, oligomers (foldamers), and helical and nonhelical polymers from the viewpoints of their formations with unique chiral phenomena, such as amplification of chirality during the dynamic helically assembled processes, properties, and specific functionalities, some of which have not been observed in or achieved by biological systems. In addition, a brief historical overview of the helical assemblies of small molecules and remarkable progress in the synthesis of single-stranded and multistranded helical foldamers and polymers, their properties, structures, and functions, mainly since 2009, will also be described.
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              Chiral architectures from macromolecular building blocks.

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                Author and article information

                Contributors
                rafael.rodriguez.riego@usc.es
                felix.freire@usc.es
                Journal
                Chirality
                Chirality
                10.1002/(ISSN)1520-636X
                CHIR
                Chirality
                John Wiley and Sons Inc. (Hoboken )
                0899-0042
                1520-636X
                10 January 2023
                March 2023
                : 35
                : 3 ( doiID: 10.1002/chir.v35.3 )
                : 172-177
                Affiliations
                [ 1 ] Centro Singular de investigación en Química Biolóxica e Materiais Moleculares (CiQUS) e Departamento de Química Orgánica Universidade de Santiago de Compostela Santiago de Compostela Spain
                Author notes
                [*] [* ] Correspondence

                Rafael Rodríguez and Félix Freire, Centro Singular de investigación en Química Biolóxica e Materiais Moleculares (CiQUS) e Departamento de Química Orgánica, Universidade de Santiago de Compostela, Santiago de Compostela 15782, Spain.

                Email: felix.freire@ 123456usc.es and rafael.rodriguez.riego@ 123456usc.es

                Author information
                https://orcid.org/0000-0002-8588-7776
                Article
                CHIR23530
                10.1002/chir.23530
                10107841
                36625726
                5627ab69-f7ef-40f7-a841-d2ed19086082
                © 2023 The Authors. Chirality published by Wiley Periodicals LLC.

                This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.

                History
                : 22 December 2022
                : 30 November 2022
                : 24 December 2022
                Page count
                Figures: 4, Tables: 0, Pages: 6, Words: 4618
                Funding
                Funded by: Xunta de Galicia , doi 10.13039/501100010801;
                Award ID: ED431C 2022/21
                Funded by: Agencia Estatal de Investigacion
                Award ID: PID2019‐109733GB‐I00
                Funded by: Juan de la Cierva Incorporación
                Award ID: IJC2020‐042689‐I
                Funded by: Centro Singular de Investigación de Galicia acreditación 2019‐2022
                Award ID: ED431G 2019/03
                Funded by: European Regional Development Fund (ERDF) , doi 10.13039/501100008530;
                Categories
                Short Communication
                Special Issue: Chiral Materials
                Short Communication
                Custom metadata
                2.0
                March 2023
                Converter:WILEY_ML3GV2_TO_JATSPMC version:6.2.7 mode:remove_FC converted:17.04.2023

                General chemistry
                chiroptical switches,diastereomers,helical polymers,helical stretching,solvent polarity

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