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Sterics and Hydrogen Bonding Control Stereochemistry and Self-Sorting in BINOL-Based Assemblies
[Image: see text] Here we demonstrate how the hydrogen-bonding ability of a BINOL-based dialdehyde subcomponent dictated the stereochemical outcome of its subsequent self-assembly into one diastereomeric helicate form when bearing free hydroxy groups, and another in the case of its methylated congen...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8227477/ https://www.ncbi.nlm.nih.gov/pubmed/34124891 http://dx.doi.org/10.1021/jacs.1c05172 |
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author | Zou, You-Quan Zhang, Dawei Ronson, Tanya K. Tarzia, Andrew Lu, Zifei Jelfs, Kim E. Nitschke, Jonathan R. |
author_facet | Zou, You-Quan Zhang, Dawei Ronson, Tanya K. Tarzia, Andrew Lu, Zifei Jelfs, Kim E. Nitschke, Jonathan R. |
author_sort | Zou, You-Quan |
collection | PubMed |
description | [Image: see text] Here we demonstrate how the hydrogen-bonding ability of a BINOL-based dialdehyde subcomponent dictated the stereochemical outcome of its subsequent self-assembly into one diastereomeric helicate form when bearing free hydroxy groups, and another in the case of its methylated congener. The presence of methyl groups also altered the self-sorting behavior when mixed with another, short linear dialdehyde subcomponent, switching the outcome of the system from narcissistic to integrative self-sorting. In all cases, the axial chirality of the BINOL building block also dictated helicate metal center handedness during stereospecific self-assembly. A new family of stereochemically pure heteroleptic helicates were thus prepared using the new knowledge gained. We also found that switching from Fe(II) to Zn(II), or the incorporation of a longer linear ligand, favored heteroleptic structure formation. |
format | Online Article Text |
id | pubmed-8227477 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-82274772021-06-25 Sterics and Hydrogen Bonding Control Stereochemistry and Self-Sorting in BINOL-Based Assemblies Zou, You-Quan Zhang, Dawei Ronson, Tanya K. Tarzia, Andrew Lu, Zifei Jelfs, Kim E. Nitschke, Jonathan R. J Am Chem Soc [Image: see text] Here we demonstrate how the hydrogen-bonding ability of a BINOL-based dialdehyde subcomponent dictated the stereochemical outcome of its subsequent self-assembly into one diastereomeric helicate form when bearing free hydroxy groups, and another in the case of its methylated congener. The presence of methyl groups also altered the self-sorting behavior when mixed with another, short linear dialdehyde subcomponent, switching the outcome of the system from narcissistic to integrative self-sorting. In all cases, the axial chirality of the BINOL building block also dictated helicate metal center handedness during stereospecific self-assembly. A new family of stereochemically pure heteroleptic helicates were thus prepared using the new knowledge gained. We also found that switching from Fe(II) to Zn(II), or the incorporation of a longer linear ligand, favored heteroleptic structure formation. American Chemical Society 2021-06-14 2021-06-23 /pmc/articles/PMC8227477/ /pubmed/34124891 http://dx.doi.org/10.1021/jacs.1c05172 Text en © 2021 The Authors. Published by American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Zou, You-Quan Zhang, Dawei Ronson, Tanya K. Tarzia, Andrew Lu, Zifei Jelfs, Kim E. Nitschke, Jonathan R. Sterics and Hydrogen Bonding Control Stereochemistry and Self-Sorting in BINOL-Based Assemblies |
title | Sterics
and Hydrogen Bonding Control Stereochemistry
and Self-Sorting in BINOL-Based
Assemblies |
title_full | Sterics
and Hydrogen Bonding Control Stereochemistry
and Self-Sorting in BINOL-Based
Assemblies |
title_fullStr | Sterics
and Hydrogen Bonding Control Stereochemistry
and Self-Sorting in BINOL-Based
Assemblies |
title_full_unstemmed | Sterics
and Hydrogen Bonding Control Stereochemistry
and Self-Sorting in BINOL-Based
Assemblies |
title_short | Sterics
and Hydrogen Bonding Control Stereochemistry
and Self-Sorting in BINOL-Based
Assemblies |
title_sort | sterics
and hydrogen bonding control stereochemistry
and self-sorting in binol-based
assemblies |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8227477/ https://www.ncbi.nlm.nih.gov/pubmed/34124891 http://dx.doi.org/10.1021/jacs.1c05172 |
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