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

Wagle, Shreyas S.; Rathee, Parul; Vippala, Krishna; Tevet, Shahar; Gordin, Alexander; Dobrovetsky, Roman; Amir, Roey J.

doi:10.1039/d3nr02012f

Nanoscale

2023

DOI: 10.1039/d3nr02012f

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

Shreyas S. Wagle,

Parul Rathee,

Krishna Vippala

et al.

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...

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2024

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Cited by 3 publications

References 47 publications

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Glass Vials Coated with Polymer‐Supported‐Catalysts as Reaction Vessels: Stir, Pour, Rinse and Reuse

Gayen,

Sardana,

Ramakrishnan

2024

Macro Chemistry & Physics

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Lightly crosslinked polymeric gel‐supported catalysts have the potential to retain the recyclability and ease of product isolation of traditional polymer‐supported catalysts, while at the same time, they can provide greater homogeneity of catalytic sites and improved reaction rates, especially in the solvent‐swollen state. In the present study, a strategy is devised to covalently anchor a film of swellable crosslinked polymer onto a suitably surface‐derivatized glass vial, and have utilized this coating to bind to Cu, Pd, and Au catalysts; these coated vials are then utilized for azide‐alkyne click, Suzuki coupling and catalytic reduction reactions, respectively. In all cases, simply stirring the reactant mixture in the vial delivers high yields, and the vials can be rinsed and reused several times with little loss of activity. Several control experiments confirm that the catalysis largely occurred within the coated gel film and is not due to leached‐out metal in the reaction medium. Importantly, this strategy can be very useful, when adapted for critical labeling reactions of biomolecules, wherein reactions are often carried out on very small scales, and ease of product isolation with zero contamination is critical.

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Glass Vials Coated with Polymer‐Supported‐Catalysts as Reaction Vessels: Stir, Pour, Rinse and Reuse

Gayen,

Sardana,

Ramakrishnan

2024

Macro Chemistry & Physics

View full text Add to dashboard Cite

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Micellar curcumol for maintenance therapy of ovarian cancer by activating the FOXO3a

Wang,

Chen,

Yang

et al. 2024

Nanomedicine: Nanotechnology, Biology and Medicine

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Micellar “Click” Nanoreactors: Spiking Pluronic-Based Micelles with Polymeric Ligands

Vippala,

Wagle,

Rathee

et al. 2024

Macromolecules

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In recent years, the development of nanoreactors, such as micellar nanoreactors (MNRs) for catalytic transformations, has gained significant attention due to their potential in enhancing reaction rates, selectivity, efficiency, and, as importantly, the ability to conduct organic chemistry in aqueous solutions. Among these, the copper(I)catalyzed azide−alkyne cycloaddition (CuAAC) reaction represents a pivotal transformation and is widely used in the synthesis of bioconjugates, pharmaceuticals, and advanced materials. This study aims toward advancing our understanding of the design and utilization of polymeric amphiphiles containing tris-triazole ligands as an integral element for CuAAC reactions within MNRs. Specifically, our investigation delves into three critical factors that influence the reaction rate within MNRs: hydrophobicity, architectural configuration of the polymeric ligands, and their concentration. Utilizing the high molecular precision of dendritic amphiphiles, we synthesized polymeric ligands with two distinct architectures, namely, PEG-ditristriazole amphiphile (DTA) and PEG-monotris-triazole amphiphile (MTA), and explored their CuAAC reactivity through coassembly with commercially available Pluronic P123 amphiphiles. The results indicate that the architecture and the concentration of the polymeric ligands play more dominant roles in influencing the reaction rate than the hydrophobicity of the dendritic blocks. Notably, while MNRs assembled from solely DTA showed a dampened reaction rate, spiking P123 micelles with DTA yielded an MNR with significantly faster rates. Moreover, P123 MNRs spiked with the synthesized MTA demonstrated increased CuAAC reaction rates compared to those spiked with the DTA, and they even outperformed the widely used Tris(benzyltriazolylmethyl)amine ligand. These findings provide valuable insights into the design principles of polymer-based ligands for constructing reactive MNRs and other types of nanoreactors for efficient catalytic transformations.

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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...

Cited by 3 publications

References 47 publications

Glass Vials Coated with Polymer‐Supported‐Catalysts as Reaction Vessels: Stir, Pour, Rinse and Reuse

Glass Vials Coated with Polymer‐Supported‐Catalysts as Reaction Vessels: Stir, Pour, Rinse and Reuse

Micellar curcumol for maintenance therapy of ovarian cancer by activating the FOXO3a

Micellar “Click” Nanoreactors: Spiking Pluronic-Based Micelles with Polymeric Ligands

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