Issue 37, 2023

Polymeric architecture as a tool for controlling the reactivity of palladium(ii) loaded nanoreactors

Abstract

Self-assembled systems, like polymeric micelles, have become great facilitators for conducting organic reactions in aqueous media due to their broad potential applications in green chemistry and biomedical applications. Massive strides have been taken to improve the reaction scope of such systems, enabling them to perform bioorthogonal reactions for prodrug therapy. Considering these significant advancements, we sought to study the relationships between the architecture of the amphiphiles and the reactivity of their PdII loaded micellar nanoreactors in conducting depropargylation reactions. Towards this goal, we designed and synthesized a series of isomeric polyethylene glycol (PEG)-dendron amphiphiles with different dendritic architectures but with an identical degree of hydrophobicity and hydrophilic to lipophilic balance (HLB). We observed that the dendritic architecture, which serves as the main binding site for the PdII ions, has greater influence on the reactivity than the hydrophobicity of the dendron. These trends remained constant for two different propargyl caged substrates, validating the obtained results. Density functional theory (DFT) calculations of simplified models of the dendritic blocks revealed the different binding modes of the various dendritic architectures to PdII ions, which could explain the observed differences in the reactivity of the nanoreactors with different dendritic architectures. Our results demonstrate how tuning the internal architecture of the amphiphiles by changing the orientation of the chelating moieties can be used as a tool for controlling the reactivity of PdII loaded nanoreactors.

Graphical abstract: Polymeric architecture as a tool for controlling the reactivity of palladium(ii) loaded nanoreactors

  • This article is part of the themed collection: Nanozymes

Supplementary files

Article information

Article type
Paper
Submitted
01 Maijs 2023
Accepted
20 Aug. 2023
First published
24 Aug. 2023
This article is Open Access
Creative Commons BY license

Nanoscale, 2023,15, 15396-15404

Polymeric architecture as a tool for controlling the reactivity of palladium(II) loaded nanoreactors

S. S. Wagle, P. Rathee, K. Vippala, S. Tevet, A. Gordin, R. Dobrovetsky and R. J. Amir, Nanoscale, 2023, 15, 15396 DOI: 10.1039/D3NR02012F

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