Polyfluoroalkyl Chain-Based Assemblies for Biomimetic Catalysis.

Autor: Liu N; College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021, China., Gao P; Institut Galien Paris-Saclay, Université Paris-Saclay, CNRS, Orsay, 91400, France.; BioCIS, Université Paris-Saclay, CNRS, Orsay, 91400, France., Lu HY; College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021, China., Fang L; College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021, China., Nicolas J; Institut Galien Paris-Saclay, Université Paris-Saclay, CNRS, Orsay, 91400, France., Ha-Duong T; BioCIS, Université Paris-Saclay, CNRS, Orsay, 91400, France., Shen JS; College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021, China.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Jan 02; Vol. 30 (1), pp. e202302669. Date of Electronic Publication: 2023 Nov 13.
DOI: 10.1002/chem.202302669
Abstrakt: Amphiphobic fluoroalkyl chains are exploited for creating robust and diverse self-assembled biomimetic catalysts. Long terminal perfluoroalkyl chains (C n F 2n+1 with n=6, 8, and 10) linked with a short perhydroalkyl chains (C m H 2m with m=2 and 3) were used to synthesize several 1,4,7-triazacyclononane (TACN) derivatives, C n F 2n+1 -C m H 2m -TACN. In the presence of an equimolar amount of Zn 2+ ions that coordinate the TACN moiety and drive the self-assembly into micelle-like aggregates, the critical aggregation concentration of polyfluorinated C n F 2n+1 -C m H 2m -TACN⋅Zn 2+ 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 C n F 2n+1 -C m H 2m -TACN⋅Zn 2+ 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 Zn 2+ ions and to better understand their enhanced catalytic activity.
(© 2023 Wiley-VCH GmbH.)
Databáze: MEDLINE
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