N-Heterocyclic Carbene Functionalized Covalent Organic Framework for Transesterification of Glycerol with Dialkyl Carbonates

The development of a heterogeneous catalyst through the combination of novel carrier and powerful catalytic active sites is of particular interest. Herein, the successful integration of an <i>N</i>-Heterocyclic carbene (NHC) moiety into a covalent organic framework (COF) was achieved by...

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Main Authors: Yuying Chai, Yaling Li, Hui Hu, Chaoyuan Zeng, Shenglin Wang, Huanjun Xu, Yanan Gao
Format: Article
Language:English
Published: MDPI AG 2021-03-01
Series:Catalysts
Subjects:
Online Access:https://www.mdpi.com/2073-4344/11/4/423
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author Yuying Chai
Yaling Li
Hui Hu
Chaoyuan Zeng
Shenglin Wang
Huanjun Xu
Yanan Gao
author_facet Yuying Chai
Yaling Li
Hui Hu
Chaoyuan Zeng
Shenglin Wang
Huanjun Xu
Yanan Gao
author_sort Yuying Chai
collection DOAJ
description The development of a heterogeneous catalyst through the combination of novel carrier and powerful catalytic active sites is of particular interest. Herein, the successful integration of an <i>N</i>-Heterocyclic carbene (NHC) moiety into a covalent organic framework (COF) was achieved by coupling 4,4′,4′′,4′′′-(pyrene-1,3,6,8-tetrayl) tetraaniline (PyTTA) and equimolar 4,7-bis(4-formylphenyl)-1-methyl-1H-benzimidazole (IM) and 2′3′5′6′-tetrafluoro-[1,1′:4′,1′′-terphenyl]-4,4′-dicarbaldehyde (4F) followed by ionization with 1-bromobutane (C<sub>4</sub>H<sub>9</sub>Br) and then deprotonation upon addition of a base. The resulting material exhibited promising heterogeneous catalytic activity towards transesterification reaction of glycerol with dialkyl carbonate. Moreover, good recyclability granted no substantial loss of activity upon five cycles. Combination of COFs and NHCs might synergize their characteristics, thus providing more possibilities for creating new patterns of catalytic reactivity.
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spelling doaj.art-fdf2ccc719c6460ab02fc67a43d940342023-11-21T12:07:11ZengMDPI AGCatalysts2073-43442021-03-0111442310.3390/catal11040423N-Heterocyclic Carbene Functionalized Covalent Organic Framework for Transesterification of Glycerol with Dialkyl CarbonatesYuying Chai0Yaling Li1Hui Hu2Chaoyuan Zeng3Shenglin Wang4Huanjun Xu5Yanan Gao6Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan University, No 58, Renmin Avenue, Haikou 570228, ChinaKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan University, No 58, Renmin Avenue, Haikou 570228, ChinaKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan University, No 58, Renmin Avenue, Haikou 570228, ChinaKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan University, No 58, Renmin Avenue, Haikou 570228, ChinaKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan University, No 58, Renmin Avenue, Haikou 570228, ChinaKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan University, No 58, Renmin Avenue, Haikou 570228, ChinaKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan University, No 58, Renmin Avenue, Haikou 570228, ChinaThe development of a heterogeneous catalyst through the combination of novel carrier and powerful catalytic active sites is of particular interest. Herein, the successful integration of an <i>N</i>-Heterocyclic carbene (NHC) moiety into a covalent organic framework (COF) was achieved by coupling 4,4′,4′′,4′′′-(pyrene-1,3,6,8-tetrayl) tetraaniline (PyTTA) and equimolar 4,7-bis(4-formylphenyl)-1-methyl-1H-benzimidazole (IM) and 2′3′5′6′-tetrafluoro-[1,1′:4′,1′′-terphenyl]-4,4′-dicarbaldehyde (4F) followed by ionization with 1-bromobutane (C<sub>4</sub>H<sub>9</sub>Br) and then deprotonation upon addition of a base. The resulting material exhibited promising heterogeneous catalytic activity towards transesterification reaction of glycerol with dialkyl carbonate. Moreover, good recyclability granted no substantial loss of activity upon five cycles. Combination of COFs and NHCs might synergize their characteristics, thus providing more possibilities for creating new patterns of catalytic reactivity.https://www.mdpi.com/2073-4344/11/4/423covalent organic frameworkcarbenecatalystglyceroltransesterification
spellingShingle Yuying Chai
Yaling Li
Hui Hu
Chaoyuan Zeng
Shenglin Wang
Huanjun Xu
Yanan Gao
N-Heterocyclic Carbene Functionalized Covalent Organic Framework for Transesterification of Glycerol with Dialkyl Carbonates
Catalysts
covalent organic framework
carbene
catalyst
glycerol
transesterification
title N-Heterocyclic Carbene Functionalized Covalent Organic Framework for Transesterification of Glycerol with Dialkyl Carbonates
title_full N-Heterocyclic Carbene Functionalized Covalent Organic Framework for Transesterification of Glycerol with Dialkyl Carbonates
title_fullStr N-Heterocyclic Carbene Functionalized Covalent Organic Framework for Transesterification of Glycerol with Dialkyl Carbonates
title_full_unstemmed N-Heterocyclic Carbene Functionalized Covalent Organic Framework for Transesterification of Glycerol with Dialkyl Carbonates
title_short N-Heterocyclic Carbene Functionalized Covalent Organic Framework for Transesterification of Glycerol with Dialkyl Carbonates
title_sort n heterocyclic carbene functionalized covalent organic framework for transesterification of glycerol with dialkyl carbonates
topic covalent organic framework
carbene
catalyst
glycerol
transesterification
url https://www.mdpi.com/2073-4344/11/4/423
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