Facile Fabrication of Hierarchical MOF–Metal Nanoparticle Tandem Catalysts for the Synthesis of Bioactive Molecules

Date
2020-05-20
Authors
Chen, Jingwen
Zhang, Biying
Qi, Long
Huang, Wenyu
Pei, Yuchen
Nie, Renfeng
Heintz, Patrick
Luan, Xuechen
Bao, Zongbi
Yang, Qiwei
Ren, Qilong
Zhang, Zhiguo
Huang, Wenyu
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Ames Laboratory
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Chemistry
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Ames LaboratoryChemistry
Abstract

Multifunctional metal–organic frameworks (MOFs) that possess permanent porosity are promising catalysts in organic transformation. Herein, we report the construction of a hierarchical MOF functionalized with basic aliphatic amine groups and polyvinylpyrrolidone-capped platinum nanoparticles (Pt NPs). The postsynthetic covalent modification of organic ligands increases basic site density in the MOF and simultaneously introduces mesopores to create a hierarchically porous structure. The multifunctional MOF is capable of catalyzing a sequential Knoevenagel condensation–hydrogenation–intramolecular cyclization reaction. The unique selective reduction of the nitro group to intermediate hydroxylamine by Pt NPs supported on MOF followed by intramolecular cyclization with a cyano group affords an excellent yield (up to 92%) to the uncommon quinoline N-oxides over quinolines. The hierarchical MOF and polyvinylpyrrolidone capping agent on Pt NPs synergistically facilitate the enrichment of substrates and thus lead to high activity in the reduction–intramolecular cyclization reaction. The bioactivity assay indicates that the synthesized quinoline N-oxides evidently inhibit the proliferation of lung cancer cells. Our findings demonstrate the feasibility of MOF-catalyzed direct synthesis of bioactive molecules from readily available compounds under mild conditions.

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This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in ACS Applied Materials & Interfaces, copyright © American Chemical Society after peer review. To access the final edited and published work see DOI: 10.1021/acsami.0c05344. Posted with permission.

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