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

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. Finally, our findings demonstrate the feasibility of MOF-catalyzed direct synthesis of bioactive molecules from readily available compounds under mild conditions.

Authors:
ORCiD logo [1];  [2]; ORCiD logo [3];  [2]; ORCiD logo [2];  [2];  [2]; ORCiD logo [4]; ORCiD logo [4];  [4]; ORCiD logo [4]; ORCiD logo [5]
  1. Zhejiang Univ., Hangzhou (China); Iowa State Univ., Ames, IA (United States)
  2. Iowa State Univ., Ames, IA (United States)
  3. Ames Lab., Ames, IA (United States)
  4. Zhejiang Univ., Hangzhou (China)
  5. Iowa State Univ., Ames, IA (United States); Ames Lab., Ames, IA (United States)
Publication Date:
Research Org.:
Ames Lab., Ames, IA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division; National Key R&D Program of China; National Natural Science Foundation of China (NNSFC); National Science Foundation (NSF)
OSTI Identifier:
1630734
Report Number(s):
IS-J-10,220
Journal ID: ISSN 1944-8244
Grant/Contract Number:  
AC02-07CH11358; 21722609; 21878266; 2016YFA0202900; CHE-1566445
Resource Type:
Accepted Manuscript
Journal Name:
ACS Applied Materials and Interfaces
Additional Journal Information:
Journal Volume: 12; Journal Issue: 20; Journal ID: ISSN 1944-8244
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; tandem reaction; metal-organic frameworks; hierarchical pore; heterogeneous catalysis; bioactivity; quinoline N-oxides

Citation Formats

Chen, Jingwen, Zhang, Biying, Qi, Long, Pei, Yuchen, Nie, Renfeng, Heintz, Patrick, Luan, Xuechen, Bao, Zongbi, Yang, Qiwei, Ren, Qilong, Zhang, Zhiguo, and Huang, Wenyu. Facile Fabrication of Hierarchical MOF–Metal Nanoparticle Tandem Catalysts for the Synthesis of Bioactive Molecules. United States: N. p., 2020. Web. doi:10.1021/acsami.0c05344.
Chen, Jingwen, Zhang, Biying, Qi, Long, Pei, Yuchen, Nie, Renfeng, Heintz, Patrick, Luan, Xuechen, Bao, Zongbi, Yang, Qiwei, Ren, Qilong, Zhang, Zhiguo, & Huang, Wenyu. Facile Fabrication of Hierarchical MOF–Metal Nanoparticle Tandem Catalysts for the Synthesis of Bioactive Molecules. United States. doi:10.1021/acsami.0c05344.
Chen, Jingwen, Zhang, Biying, Qi, Long, Pei, Yuchen, Nie, Renfeng, Heintz, Patrick, Luan, Xuechen, Bao, Zongbi, Yang, Qiwei, Ren, Qilong, Zhang, Zhiguo, and Huang, Wenyu. Mon . "Facile Fabrication of Hierarchical MOF–Metal Nanoparticle Tandem Catalysts for the Synthesis of Bioactive Molecules". United States. doi:10.1021/acsami.0c05344.
@article{osti_1630734,
title = {Facile Fabrication of Hierarchical MOF–Metal Nanoparticle Tandem Catalysts for the Synthesis of Bioactive Molecules},
author = {Chen, Jingwen and Zhang, Biying and Qi, Long and Pei, Yuchen and Nie, Renfeng and Heintz, Patrick and Luan, Xuechen and Bao, Zongbi and Yang, Qiwei and Ren, Qilong and Zhang, Zhiguo and Huang, Wenyu},
abstractNote = {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. Finally, our findings demonstrate the feasibility of MOF-catalyzed direct synthesis of bioactive molecules from readily available compounds under mild conditions.},
doi = {10.1021/acsami.0c05344},
journal = {ACS Applied Materials and Interfaces},
number = 20,
volume = 12,
place = {United States},
year = {2020},
month = {4}
}

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This content will become publicly available on April 27, 2021
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