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  • Amine COFs Linkers

    Introduction

    Covalent organic frameworks (COFs) are interesting crystalline porous polymeric materials consisting of organic building blocks linked by covalent bonds. Among many organic building blocks, the linkers containing amine functional groups are one of representative linkers. Amine COFs linkers can contain one amine group, two amine groups, three amine groups, four amine groups or even multiple amine groups, so amine COFs linkers can be further divided into monomeric amine linkers, ditopic amine linkers, tritopic amine linkers, tetratopic amine linkers, multi-amine linkers, etc. These linkers have been used to build many types of COFs materials, and the imine-linked COFs formed by Schiff base reaction between amine linkers and aldehyde linkers are the most famous, which constitute the most widely studied subclass of COFs owing to their broad synthetic scope and facile building block synthesis.

    Fig. 1. Typical examples of COFs linkers with amine functional groups.Fig. 1. Typical examples of COFs linkers with amine functional groups.

    Applications

    Amine-containing linkers can be used to form different linkages for the construction of different types of COFs materials. Typical COFs synthesis applications are shown in below.

    • Synthesis of imine-linked COFs: As mentioned above, one of typical COFs synthesis applications of amine-containing monomers is to synthesize imine-linked COFs. Aromatic amine linkers react with aldehyde in the presence of organic acid or Lewis acid catalyst that can form imine-linked COFs. And this type of COFs has higher chemical stability compared to classic boroxines and boronic esters linked COFs. According to the topology diagrams, the imine-linked 2D COFs with hexagonal, tetragonal, rhombic, kagome, and trigonal architectures can be made by this strategy [1].

    Fig. 2. Schematic for the synthesis of a imine-linked COF (TPB-DMTP-COF) by amine linkers.Fig. 2. Schematic for the synthesis of a imine-linked COF (TPB-DMTP-COF) by amine linkers.

    • Synthesis of imide-linked COFs: Amines-containing linkers and their derivatives can be condensed with acetic anhydride to obtain imide-linked COFs under a high reaction temperature as high as 250 °C. For examples, mesoporous 2D PI-COF-1, PI-COF-2, and PI-COF-3 have been synthesized by this strategy under solvothermal conditions in a mixture of N-methyl-2-pyrrolidone (NMP)/mesitylene/isoquinoline (10/10/1 v/v/v). The PI-COF-1 and PI-COF-2 have been prepared upon reaction at 200 °C for 5 days, whereas PI-COF-3 is obtained under 250 °C for 7 days[1]. The obtained imide-linked COFs are expected to be applied to battery materials and CO2 capture materials.

    Fig. 3. Schematics for the synthesis of 2D PI-COF-1, PI-COF-2, and PI-COF-3 by amine linkers.Fig. 3. Schematics for the synthesis of 2D PI-COF-1, PI-COF-2, and PI-COF-3 by amine linkers.

    • Synthesis of C=N bond linked COFs: Linkers containing amine group can also be connected to squaraines for forming C=N bond linked COFs. Nowaday, COFs containing squaraine with a zigzag conformation have been constructed by this method and show high stability in solvents due to that the zigzag conformation protected the layered structure from slipping [2].
    • Synthesis of C–N bond linked COFs: Monomer containing o-phenylenediamine group reacts with the monomer with α-dicarbonyl group that can form COFs with C–N linkage. In addition, monomer containing phenylamino group combines with the monomer of 1,3,5-triformylphloroglucinol that can also form C–N bond linked COFs.

    Alfa Chemistry offers a series of amine COFs linkers such as monomeric amine linkers, ditopic amine linkers, tritopic amine linkers, tetratopic amine linkers, multi-amine linkers, etc. These linkers have been widely used to construct imine-linked COFs, imide-linked COFs COFs, C=N bond linked COFs, C–N bond linked COFs, etc. You can click on our product list for a detailed view. At the same time, we also offer product customization according to customer's detailed requirements. If you are interested in our products or have any questions or needs, please feel free to contact us. We will be happy to provide you with support and services.

    References:

    1. Geng K., et al. Covalent organic frameworks: design, synthesis, and functions[J]. Chemical Reviews, 2020, 120(16): 8814-8933.
    2. Li S., et al. Covalent organic frameworks: from linkages to biomedical applications[J]. Chemical Engineering Journal, 2022, 446: 137148.

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