Site-selective synthesis of an amine-functionalized β-ketoenamine-linked covalent organic framework for improved detection and removal of Cu2+ ion from water

Dong, Zhaoyi; Yang, Yaqiong; Cai, Xinting; Tang, Xihao; Yan, Yilun; Zheng, Sheng‐Run; Zhang, Weiguang; Cai, Song‐Liang; Fan, Jun

doi:10.1016/j.jssc.2022.123644

Cited by 17 publications

(13 citation statements)

References 47 publications

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“…Due to the larger π-conjugated and more coplanar structure of the Tz linker, stronger π–π stacking interactions could be achieved during the 2D COF synthesis. This led to a higher degree of crystallinity in the obtained NH 2 -Th-Tz COF compared to previously amine-functionalized COFs obtained by the site-selective synthetic strategy. , Additionally, it could be inferred that the resulting hydrazone-linked NH 2 -Th-Tz COF was chemically stable owing to the robust hydrazone linkage in the 2D framework. , As expected, upon postmodification of NH 2 -Th-Tz COF with carboxylic acid, acyl chloride, and anhydride under mild reaction conditions, the obtained three D -Tart-Th-Tz, L -Cam-Th-Tz, and L -Dta-Th-Tz chiral COFs still retained high crystallinity. As shown in Figure a, the PXRD patterns of three chiral COFs exhibited similar patterns to that of the parent COF, indicating the isostructural nature of these chiral COFs, which all adopted the AA packing modes (Figure b–d).…”

Section: Resultssupporting

confidence: 56%

“…This led to a higher degree of crystallinity in the obtained NH 2 -Th-Tz COF compared to previously amine-functionalized COFs obtained by the site-selective synthetic strategy. 43,44 Additionally, it could be inferred that the resulting hydrazone-linked NH 2 -Th-Tz COF was chemically stable owing to the robust hydrazone linkage in the 2D framework. 17,25 As expected, upon postmodification of NH 2 -Th-Tz COF with carboxylic acid, acyl chloride, and anhydride under mild reaction conditions, the obtained three D-Tart-Th-Tz, L-Cam-Th-Tz, and L-Dta-Th-Tz chiral COFs still retained high crystallinity.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Specifically, a linker of aminoterephthalohydrazide (NH 2 -Th) containing both hydrazide and amine functional groups was designed to react with trialdehyde, leading to the formation of the hydrazone-linked COFs with free amine function groups, which provide abundant modification sites to covalently attach desired moieties. 43,44 However, the previously reported aminefunctionalized COFs exhibited relatively low crystallinity and poor porosity, which, to some extent, restrict their further applications. The crystalline nature of the amine-functionalized NH 2 -Th-Tz COF was evaluated by the powder X-ray diffraction (PXRD) analysis.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…To synthesize the amine-functionalized COFs, we developed a site-selective synthetic strategy in our previous work. Specifically, a linker of aminoterephthalohydrazide (NH 2 -Th) containing both hydrazide and amine functional groups was designed to react with trialdehyde, leading to the formation of the hydrazone-linked COFs with free amine function groups, which provide abundant modification sites to covalently attach desired moieties. , However, the previously reported amine-functionalized COFs exhibited relatively low crystallinity and poor porosity, which, to some extent, restrict their further applications. To this end, a new amine-functionalized hydrazone-linked COF, NH 2 -Th-Tz COF, was synthesized by condensing NH 2 -Th with 4,4′,4″-(1,3,5-triazine-2,4,6-triyl)tribenzaldehyde (Tz).…”

Section: Resultsmentioning

confidence: 99%

“…In our previous work, we reported a unique site-selective synthetic strategy for the de novo synthesis of amine-functionalized COFs, , in which the free amine groups provide ample opportunities for postmodification. Nevertheless, further application, to some extent, was hindered by the inferior crystallinity and porosity of the obtained COFs.…”

Section: Introductionmentioning

confidence: 99%

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Postmodification of an Amine-Functionalized Covalent Organic Framework for Enantioselective Adsorption of Tyrosine

Tang

Yang

et al. 2023

ACS Appl. Mater. Interfaces

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The development of chiral covalent organic frameworks (COFs) by postsynthetic modification is challenging due to the common occurrences of racemization and crystallinity decrement under harsh modification conditions. Herein, we employ an effective site-selective synthetic strategy for the fabrication of an amine-functionalized hydrazone-linked COF, NH2-Th-Tz COF, by the Schiff-base condensation between aminoterephthalohydrazide (NH2-Th) and 4,4′,4″-(1,3,5-triazine-2,4,6-triyl)tribenzaldehyde (Tz). The resulting NH2-Th-Tz COF with free amine groups on the pore walls provides an appealing platform to install desired chiral moieties through postsynthetic modification. Three chiral moieties including tartaric acid, camphor-10-sulfonyl chloride, and diacetyl-tartaric anhydride were postsynthetically integrated into NH2-Th-Tz COF by reacting amine groups with acid, acyl chloride, and anhydride, giving rise to a series of chiral COFs with distinctive chiral pore surfaces. Moreover, the crystallinity, porosity, and chirality of chiral COFs were retained after modification. Remarkably, the chiral COFs exhibited an exceptional enantioselective adsorption capability toward tyrosine with a maximum enantiomeric excess (ee) value of up to 25.20%. Molecular docking simulations along with experimental results underscored the pivotal role of hydrogen bonds between chiral COFs and tyrosine in enantioselective adsorption. This work highlights the potential of site-selective synthesis as an effective tool for the preparation of highly crystalline and robust amine-decorated COFs, which offer an auspicious platform for the facile synthesis of tailor-made chiral COFs for enantioselective adsorption and beyond.

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Section: Resultssupporting

confidence: 56%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Postmodification of an Amine-Functionalized Covalent Organic Framework for Enantioselective Adsorption of Tyrosine

Tang

Yang

et al. 2023

ACS Appl. Mater. Interfaces

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Tuning the Topology of Two‐Dimensional Covalent Organic Frameworks through Site‐Selective Synthetic Strategy

Wu,

Tang,

Zhang

et al. 2024

Chemistry A European J

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Tuning the topology of two‐dimensional (2D) covalent organic frameworks (COFs) is of paramount scientific interest but remains largely unexplored. Herein, we present a site‐selective synthetic strategy that enables the tuning of 2D COF topology by simply adjusting the molar ratio of an amine‐functionalized dihydrazide monomer (NH2‐Ah) and 4,4',4''‐(1,3,5‐triazine‐2,4,6‐triyl)tribenzaldehyde (Tz). This approach resulted in the formation of two distinct COFs: a clover‐like 2D COF with free amine groups (NH2‐Ah‐Tz) and a honeycomb‐like COF without amine groups (Ah‐Tz). Both COFs exhibited good crystallinity and moderate porosity. Remarkably, the clover‐shaped NH2‐Ah‐Tz COF, with abundant free amine groups, displayed significantly enhanced adsorption capacities toward crystal violet (CV, 261 mg/g) and congo red (CR, 1560 mg/g) compared to the nonfunctionalized honeycomb‐like Ah‐Tz COF (123 mg/g for CV and 1340 mg/g for CR), underscoring the pivotal role of free amine functional groups in enhancing adsorption capacities for organic dyes. This work highlights that the site‐selective synthetic strategy paves a new avenue for manipulating 2D COF topology by adjusting the monomer feeding ratio, thereby modulating their adsorption performances toward organic dyes.

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Synthesis of covalent organic framework materials and their application in the field of sensing

Zhang,

Liu,

Sun

et al. 2023

Nano Res.

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Site-selective synthesis of an amine-functionalized β-ketoenamine-linked covalent organic framework for improved detection and removal of Cu2+ ion from water

Cited by 17 publications

References 47 publications

Postmodification of an Amine-Functionalized Covalent Organic Framework for Enantioselective Adsorption of Tyrosine

Postmodification of an Amine-Functionalized Covalent Organic Framework for Enantioselective Adsorption of Tyrosine

Tuning the Topology of Two‐Dimensional Covalent Organic Frameworks through Site‐Selective Synthetic Strategy

Synthesis of covalent organic framework materials and their application in the field of sensing

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