Multi-Functionalization of Solid Support via Zn(II)-Mediated Chirality-Directed Self-Assembly

Max S. Overshiner; Shuyuan Tian; Kegan B. Morrow; Jailyn R. Wendt; John Zhou; Hannah M. Briggs; Gerardo B. Márquez; Kathleen V. Kilway; Shin A. Moteki

doi:10.1055/a-2106-9071

Organic Materials, Table of Contents

CC BY 4.0 · Organic Materials 2023; 05(02): 158-165
DOI: 10.1055/a-2106-9071

Original Article

Multi-Functionalization of Solid Support via Zn(II)-Mediated Chirality-Directed Self-Assembly

Max S. Overshiner

¹Division of Energy, Matter, and System, School of Science and Engineering, University of Missouri – Kansas City, Kansas City, Missouri 64110, USA

,

Shuyuan Tian

¹Division of Energy, Matter, and System, School of Science and Engineering, University of Missouri – Kansas City, Kansas City, Missouri 64110, USA

,

Kegan B. Morrow

¹Division of Energy, Matter, and System, School of Science and Engineering, University of Missouri – Kansas City, Kansas City, Missouri 64110, USA

,

Jailyn R. Wendt

¹Division of Energy, Matter, and System, School of Science and Engineering, University of Missouri – Kansas City, Kansas City, Missouri 64110, USA

,

John Zhou

¹Division of Energy, Matter, and System, School of Science and Engineering, University of Missouri – Kansas City, Kansas City, Missouri 64110, USA

,

Hannah M. Briggs

¹Division of Energy, Matter, and System, School of Science and Engineering, University of Missouri – Kansas City, Kansas City, Missouri 64110, USA

,

Gerardo B. Márquez

¹Division of Energy, Matter, and System, School of Science and Engineering, University of Missouri – Kansas City, Kansas City, Missouri 64110, USA

,

Kathleen V. Kilway

¹Division of Energy, Matter, and System, School of Science and Engineering, University of Missouri – Kansas City, Kansas City, Missouri 64110, USA

,

Shin A. Moteki

¹Division of Energy, Matter, and System, School of Science and Engineering, University of Missouri – Kansas City, Kansas City, Missouri 64110, USA

› Author Affiliations

Abstract

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Abstract

Establishing a strategy for realizing programmed self-assembly is critical in manufacturing materials with functional hybrid structures. In this work, we introduce a robust methodology for enabling multi-component self-assembly using the concept of chirality-directed self-assembly. A specific combination of heterochiral Zn(II) methylene bis(oxazoline) (BOX) complexes can be selectively generated when combinations of enantiomers of chiral BOX ligands are mixed in the presence of Zn(Oac)₂. The resulting Zn(II) BOX complexes, unlike non-covalent bonds, are highly stable and stay intact at elevated temperatures, yet can be reversibly disintegrated under mild conditions using EDTA. This approach can be easily applied to multi-functionalize various solid supports enabling the one-pot generation of multi-functional hybrid structures.

Key words

chirality-driven self-assembly - multi-functionalization - heterochiral metal–ligand complexes

Full Text

References

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18 See the Supporting Information for full ¹H NMR comparisons.
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Supplementary Material

Supporting Information for this article is available online.