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. 2024 Jan 2;30(1):e202302669.
doi: 10.1002/chem.202302669. Epub 2023 Nov 13.

Polyfluoroalkyl Chain-Based Assemblies for Biomimetic Catalysis

Ning Liu  1 , Ping Gao  2   3 , Hai-Yan Lu  1 , Lei Fang  1 , Julien Nicolas  2 , Tâp Ha-Duong  3 , Jiang-Shan Shen  1
Affiliations

Polyfluoroalkyl Chain-Based Assemblies for Biomimetic Catalysis

Ning Liu et al. Chemistry. .

Abstract

Amphiphobic fluoroalkyl chains are exploited for creating robust and diverse self-assembled biomimetic catalysts. Long terminal perfluoroalkyl chains (Cn F2n+1 with n=6, 8, and 10) linked with a short perhydroalkyl chains (Cm H2m with m=2 and 3) were used to synthesize several 1,4,7-triazacyclononane (TACN) derivatives, Cn F2n+1 -Cm H2m -TACN. In the presence of an equimolar amount of Zn2+ ions that coordinate the TACN moiety and drive the self-assembly into micelle-like aggregates, the critical aggregation concentration of polyfluorinated Cn F2n+1 -Cm H2m -TACN⋅Zn2+ was lowered by ∼1 order of magnitude compared to the traditional perhyroalkyl counterpart with identical carbon number of alkyl chain. When 2'-hydroxypropyl-4-nitrophenyl phosphate was used as the model phosphate substrate, polyfluorinated Cn F2n+1 -Cm H2m -TACN⋅Zn2+ assemblies showed higher affinity and catalytic activity, compared to its perhyroalkyl chain-based counterpart. Coarse-grained molecular dynamic simulations have been introduced to explore the supramolecular assembly of polyfluoroalkyl chains in the presence of Zn2+ ions and to better understand their enhanced catalytic activity.

Keywords: catalysis diversity; catalysis modulation; polyfluoroalkyl chain; robust assemblies; supramolecular catalysis.

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