Construction of Covalent Organic Frameworks via Photocatalytic Cascade Reaction

doi:10.6023/cjoc202407036

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (5): 1707-1715.DOI: 10.6023/cjoc202407036 Previous Articles Next Articles

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光催化串联反应构建共价有机框架

牛丽菁, 吴成娟^*(), 梁文静, 耿琰^*(), 董育斌^*()

山东师范大学化学化工与材料科学学院济南 250014

收稿日期:2024-07-24 修回日期:2024-10-28 发布日期:2024-11-20
基金资助:
国家自然科学基金(22371172); 国家自然科学基金(22101158); 国家自然科学基金(22171169); 山东省自然科学基金(ZR2021MB088)

Construction of Covalent Organic Frameworks via Photocatalytic Cascade Reaction

Lijing Niu, Chengjuan Wu^*(), Wenjing Liang, Yan Geng^*(), Yubin Dong^*()

College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014

Received:2024-07-24 Revised:2024-10-28 Published:2024-11-20
Contact: * E-mail: yubindong@sdnu.edu.cn; gengyan@sdnu.edu.cn; wucj@sdnu.edu.cn
Supported by:
National Natural Science Foundation of China(22371172); National Natural Science Foundation of China(22101158); National Natural Science Foundation of China(22171169); Natural Science Foundation of Shandong Province(ZR2021MB088)

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Abstract

Developing novel strategies for the construction of covalent organic frameworks (COFs) is always the focus of current research. Recently, the visible-light mediated photocatalysis has been introduced to produce COFs, due to its mild and green characteristics. However, there are still rare reports about the photocatalytic synthesis of COFs. Herein, a series of imine-linked COFs including TAPB-PDA-COF, TAPT-PDA-COF, TZ-BTCA-COF, and COF-LZU1 (TAPB, 1,3,5-tris-(4- aminophenyl)benzene; PDA, terephthalaldehyde; TAPT, 2,4,6-tris(4-aminophenyl)-1,3,5-triazine; TZ, 2,4,6-tris(4-amino- phenyl)-1,3,5-triazine; BTCA, 1,3,5-benzenetricarbaldehyde) were successfully synthesized via the photocatalytic cascade reaction using the benzyl alcohols and amines as the starting materials. The reaction proceeded via the sequential photo- catalytic oxidation of benzyl alcohols and imine condensation steps to generate the imine-linked COFs. Furthermore, the obtained TZ-BTCA-COF was employed as the photocatalyst to promote the photocatalytic oxidation of sulfides, affording sulfoxides in good yields. It is believed that this work not only enriches the photocatalytic synthetic methodology of COFs, but also expands the scope of monomers for COFs synthesis to benzyl alcohols, providing a new way for COFs synthesis.

Key words: covalent organic frameworks, photocatalysis, cascade reaction

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Lijing Niu, Chengjuan Wu, Wenjing Liang, Yan Geng, Yubin Dong. Construction of Covalent Organic Frameworks via Photocatalytic Cascade Reaction[J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1707-1715.

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Fig. & Tab. 10

Scheme 1. Photocatalytic benzyl alcohol oxidation and imine condensation cascade reaction

Scheme 2. Synthesis of COFs via photocatalytic benzyl alcohol oxidation and imine condensation cascade reaction

Figure 1. FT-IR spectra of (a) TAPB-PDA-COF, (b) TAPT-PDA-COF, (c) TZ-BTCA-COF and (d) COF-LZU1

Figure 2. PXRD patterns of (a) TAPB-PDA-COF, (b) TAPT-PDA-COF, (c) TZ-BTCA-COF and (d) COF-LZU1

Figure 3. SEM images of (a) TAPB-PDA-COF, (b) TAPT-PDA-COF, (c) TZ-BTCA-COF and (d) COF-LZU1

Figure 4. UV-Vis spectra of (a) TAPB-PDA-COF, (b) TAPT-PDA-COF, (c) TZ-BTCA-COF and (d) COF-LZU1

Entry	TZ-BTCA-COF/mg	Oxidant	Solvent	Yield^b/%
1	6	O₂	EtOH	83
2	6	O₂	MeOH	99
3	6	O₂	CH₃CN	68
4	6	O₂	THF	66
5	6	O₂	CH₂Cl₂	42
6	6	O₂	CHCl₃	60
7	6	O₂	Acetone	43
8	4	O₂	MeOH	96
9	8	O₂	MeOH	98
10^c	6	O₂	MeOH	20
11^d	6	O₂	MeOH	32
12^e	6	O₂	MeOH	N.R.
13	6	Air	MeOH	59
14	6	N₂	MeOH	N.R.
15	—	O₂	MeOH	N.R.

Table 1. Optimization of the reaction conditions

Figure 5. (a) Leaching test and (b) the catalytic cycles

Table 2. Scope of the photooxidation reaction

Scheme 3. Proposed mechanism of the photooxidation reaction

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光催化串联反应构建共价有机框架

Construction of Covalent Organic Frameworks via Photocatalytic Cascade Reaction

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