Synthesis of Propenone-linked Covalent Organic Frameworks Via Claisen-Schmidt Reaction for Photocatalytic Removal of Uranium

Overview

Journal Nat Commun

Specialty Biology

Date 2023 Jul 21

PMID 37479725

Authors

Cheng-Peng Niu

Cheng-Rong Zhang

Xin Liu

Ru-Ping Liang

Jian-Ding Qiu

Affiliations

Soon will be listed here.

Abstract

The type of reactions and the availability of monomers for the synthesis of sp-c linked covalent organic frameworks (COFs) are considerably limited by the irreversibility of the C=C bond. Herein, inspired by the Claisen-Schmidt condensation reaction, two propenone-linked (C=C-C=O) COFs (named Py-DAB and PyN-DAB) are developed based on the base-catalyzed nucleophilic addition reaction of ketone-activated α-H with aromatic aldehydes. The introduction of propenone structure endows COFs with high crystallinity, excellent physicochemical stability, and intriguing optoelectronic properties. Benefitting from the rational design on the COFs skeleton, Py-DAB and PyN-DAB are applied to the extraction of radionuclide uranium. In particular, PyN-DAB shows excellent removal rates (>98%) in four uranium mine wastewater samples. We highlight that such a general strategy can provide a valuable avenue toward various functional porous crystalline materials.

Citing Articles

Electron-deficient two-dimensional poly(arylene vinylene) covalent organic frameworks: efficient synthesis and host-guest interaction.

Waentig A, Li X, Zhao M, Haldar S, Koko P, Paasch S Chem Sci. 2025; 16(9):4152-4158.

PMID: 39906377 PMC: 11788921. DOI: 10.1039/d4sc06903j.

Ocean wave-driven covalent organic framework/ZnO heterostructure composites for piezocatalytic uranium extraction from seawater.

Qi J, Gong J, Zhang C, Peng Z, Cai Y, Liu X Nat Commun. 2025; 16(1):1078.

PMID: 39870660 PMC: 11772866. DOI: 10.1038/s41467-025-56471-z.

Coordination-Induced Magnetism Strategy for Highly Selective and Efficient Uranium Separation.

Zhao S, Feng T, Zhang J, Cao M, Feng L, Ma Y Adv Sci (Weinh). 2024; 11(48):e2408642.

PMID: 39494591 PMC: 11672296. DOI: 10.1002/advs.202408642.

Cairo pentagon tessellated covalent organic frameworks with mcm topology for near-infrared phototherapy.

Liu Y, Yuan L, Chi W, Han W, Zhang J, Pang H Nat Commun. 2024; 15(1):7150.

PMID: 39168967 PMC: 11339432. DOI: 10.1038/s41467-024-50761-8.

An imidazole-based covalent-organic framework enabling a super-efficiency in sunlight-driven uranium extraction from seawater.

Zhong L, Feng X, Zhang Q, Xie X, Luo F Chem Sci. 2024; 15(28):10882-10891.

PMID: 39027273 PMC: 11253174. DOI: 10.1039/d4sc02554g.

References

Rabbani M, Sekizkardes A, Kahveci Z, Reich T, Ding R, El-Kaderi H . A 2D mesoporous imine-linked covalent organic framework for high pressure gas storage applications. Chemistry. 2013; 19(10):3324-8. DOI: 10.1002/chem.201203753. View

Niu C, Zhang C, Cui W, Yi S, Liang R, Qiu J . A conveniently synthesized redox-active fluorescent covalent organic framework for selective detection and adsorption of uranium. J Hazard Mater. 2021; 425:127951. DOI: 10.1016/j.jhazmat.2021.127951. View

Li Y, Cui W, Jiang Q, Wu Q, Liang R, Luo Q . A general design approach toward covalent organic frameworks for highly efficient electrochemiluminescence. Nat Commun. 2021; 12(1):4735. PMC: 8342611. DOI: 10.1038/s41467-021-25013-8. View

Wei S, Zhang W, Qiang P, Yu K, Fu X, Wu D . Semiconducting 2D Triazine-Cored Covalent Organic Frameworks with Unsubstituted Olefin Linkages. J Am Chem Soc. 2019; 141(36):14272-14279. DOI: 10.1021/jacs.9b06219. View

Chen Z, Wang J, Hao M, Xie Y, Liu X, Yang H . Tuning excited state electronic structure and charge transport in covalent organic frameworks for enhanced photocatalytic performance. Nat Commun. 2023; 14(1):1106. PMC: 9970987. DOI: 10.1038/s41467-023-36710-x. View

Liu Y, Fu S, Pastoetter D, Khan A, Zhang Y, Dianat A . Vinylene-Linked 2D Conjugated Covalent Organic Frameworks by Wittig Reactions. Angew Chem Int Ed Engl. 2022; 61(49):e202209762. PMC: 10098612. DOI: 10.1002/anie.202209762. View

Yang P, Li S, Liu C, Liu X . Interface-Constrained Layered Double Hydroxides for Stable Uranium Capture in Highly Acidic Industrial Wastewater. ACS Appl Mater Interfaces. 2021; 13(15):17988-17997. DOI: 10.1021/acsami.1c01960. View

Wang H, Shao Y, Mei S, Lu Y, Zhang M, Sun J . Polymer-Derived Heteroatom-Doped Porous Carbon Materials. Chem Rev. 2020; 120(17):9363-9419. DOI: 10.1021/acs.chemrev.0c00080. View

Li X, Zou Y, Jia Z, Zhang J, Li Y, Guo X . A fully conjugated organic polymer via Knoevenagel condensation for fast separation of uranium. J Hazard Mater. 2020; 401:123802. DOI: 10.1016/j.jhazmat.2020.123802. View

10.

Abney C, Mayes R, Saito T, Dai S . Materials for the Recovery of Uranium from Seawater. Chem Rev. 2017; 117(23):13935-14013. DOI: 10.1021/acs.chemrev.7b00355. View

11.

Cui W, Li F, Xu R, Zhang C, Chen X, Yan R . Regenerable Covalent Organic Frameworks for Photo-enhanced Uranium Adsorption from Seawater. Angew Chem Int Ed Engl. 2020; 59(40):17684-17690. DOI: 10.1002/anie.202007895. View

12.

Yu S, Pang H, Huang S, Tang H, Wang S, Qiu M . Recent advances in metal-organic framework membranes for water treatment: A review. Sci Total Environ. 2021; 800:149662. DOI: 10.1016/j.scitotenv.2021.149662. View

13.

Man Z, Safaei J, Zhang Z, Wang Y, Zhou D, Li P . Serosa-Mimetic Nanoarchitecture Membranes for Highly Efficient Osmotic Energy Generation. J Am Chem Soc. 2021; 143(39):16206-16216. DOI: 10.1021/jacs.1c07392. View

14.

Pastoetter D, Xu S, Borrelli M, Addicoat M, Biswal B, Paasch S . Synthesis of Vinylene-Linked Two-Dimensional Conjugated Polymers via the Horner-Wadsworth-Emmons Reaction. Angew Chem Int Ed Engl. 2020; 59(52):23620-23625. PMC: 7814668. DOI: 10.1002/anie.202010398. View

15.

Xu J, Yang C, Bi S, Wang W, He Y, Wu D . Vinylene-Linked Covalent Organic Frameworks (COFs) with Symmetry-Tuned Polarity and Photocatalytic Activity. Angew Chem Int Ed Engl. 2020; 59(52):23845-23853. DOI: 10.1002/anie.202011852. View

16.

Acharjya A, Pachfule P, Roeser J, Schmitt F, Thomas A . Vinylene-Linked Covalent Organic Frameworks by Base-Catalyzed Aldol Condensation. Angew Chem Int Ed Engl. 2019; 58(42):14865-14870. PMC: 6851556. DOI: 10.1002/anie.201905886. View

17.

Zhang M, Li Y, Ma L, Guo X, Li X, Li K . Crystalline quantum dots of covalent organic frameworks for fast and sensitive detection of uranium. Chem Commun (Camb). 2019; 56(6):880-883. DOI: 10.1039/c9cc08278f. View

18.

Li X, Xu H, Leng K, Chee S, Zhao X, Jain N . Partitioning the interlayer space of covalent organic frameworks by embedding pseudorotaxanes in their backbones. Nat Chem. 2020; 12(12):1115-1122. DOI: 10.1038/s41557-020-00562-5. View

19.

Li Y, Guo X, Li X, Zhang M, Jia Z, Deng Y . Redox-Active Two-Dimensional Covalent Organic Frameworks (COFs) for Selective Reductive Separation of Valence-Variable, Redox-Sensitive and Long-Lived Radionuclides. Angew Chem Int Ed Engl. 2019; 59(10):4168-4175. DOI: 10.1002/anie.201916360. View

20.

Bi S, Zhang Z, Meng F, Wu D, Chen J, Zhang F . Heteroatom-Embedded Approach to Vinylene-Linked Covalent Organic Frameworks with Isoelectronic Structures for Photoredox Catalysis. Angew Chem Int Ed Engl. 2021; 61(6):e202111627. DOI: 10.1002/anie.202111627. View