缩醛胺共价有机框架

doi:10.6023/cjoc202604053

摘要/Abstract

共价有机框架(COF)作为一类晶态有机多孔聚合物, 凭借独特结构与性能在多个领域展现出广阔的应用前景, 而连接键是调控其性能、拓展其应用的关键位点. 缩醛胺具有四面体构型和良好的反应可逆性, 此前长期局限于有机合成领域. 2019年缩醛胺键连COF(缩醛胺COF)首次被报道, 填补了其在晶态多孔材料领域的空白, 该类COF表现出独特的理化性质与应用潜力. 然而, 受成键方式特别、单体种类有限且结构匹配性要求高等因素制约, 目前缩醛胺COF的研究十分匮乏, 其发展与潜在应用价值不匹配. 以缩醛胺COF的拓扑结构为分类依据, 系统总结其结构特点、理化性质与应用领域, 剖析研究现状与核心瓶颈, 展望未来研究方向, 为这一新类型COF的结构设计、性能优化及应用拓展提供参考, 推动缩醛胺COF领域的发展.

关键词: 共价有机框架, 缩醛胺, 连接键, 四面体构型, 拓扑结构

Covalent organic frameworks (COFs) are crystalline organic porous polymers with promising applications in many fields owing to their distinctive structures and properties. Linkages serve as critical targets for modulating their physicochemical performance and expanding application scopes. Aminal linkages possess tetrahedral configuration and favorable reaction reversibility, which have been merely confined to organic synthesis for a long period. Aminal-linked COFs were first reported in 2019, which filled the research gap in crystalline porous materials. Such materials display unique physicochemical properties and tremendous functional potentials. Nevertheless, current studies on aminal-linked COFs are extremely scarce. Their development progress fails to match their potential application value, owing to unique bond formation, high requirement for structural matching, and limited monomers. Accordingly, on the basis of topological classifications, this review systematically summarizes the structural characteristics, physicochemical properties and application fields of aminal-linked COFs. We further analyze the current research status and major bottlenecks, and prospect future research directions. This work is expected to provide references for structural design, performance optimization and application extension, and promote the further development of aminal-linked COFs.

Key words: covalent organic frameworks (COFs), aminal, linkage, tetrahedral configuration, topological structure

引用此文

高泽昕, 王桢学, 王文壮, 齐巧艳, 梁荣冉, 赵新. 缩醛胺共价有机框架[J]. 有机化学, 2026, 46(9): 3356-3371.

Zexin Gao, Zhenxue Wang, Wenzhuang Wang, Qiaoyan Qi, Rongran Liang, Xin Zhao. Aminal-Linked Covalent Organic Frameworks[J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3356-3371.

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图/表 15

图1. COF的连接键示例

Figure 1. Examples of linkages in COFs

图2. 已报道的具有不同拓扑结构的缩醛胺COF总结

Figure 2. Summary of reported aminal-linked COFs with different topologies

图3. (a) Aminal-COF-1与Aminal-COF-2的合成; (b) Aminal-COF-1、(c) Aminal-COF-2的PXRD图谱及不同堆积模型的晶体结构模拟; (d) Aminal-COF-1、(e) Aminal-COF-2的氮气吸附-脱附等温线与孔径分布曲线

Figure 3. (a) Synthesis of Aminal-COF-1 and Aminal-COF-2; PXRD patterns and simulated crystal structures with different stacking modes of (b) Aminal-COF-1 and (c) Aminal-COF-2; N2 adsorption-desorption isotherms and pore size distribution profiles of (d) Aminal- COF-1 and (e) Aminal-COF-2 Copyright 2019, American Chemical Society.

图4. 用于GSH检测的AIECL传感器作用机制示意图

图5. 用于识别苯丙氨酸对映体的ECL传感器作用机制示意图

图6. (a)已报道荧光COF和二维共轭聚合物的绝对固态光致发光量子产率总结; (b)高发光性能COF的设计策略

Figure 6. (a) Absolute solid-state photoluminescence quantum yields of reported luminescent COFs and 2D conjugated polymers; (b) Design strategies for highly luminescent COFs Copyright 2024, American Chemical Society.

图7. (a) Por-Aminal-COF的合成; (b) Por-Aminal-COF催化CEES光氧化反应的1H NMR分析

图8. (a)缩醛胺COF构筑的单体结构要求示意图; (b) TPTA-Pz-COF的化学结构

图9. PA-TA-COF的(a)合成路线、(b) PXRD图谱、(c)氮气吸附-脱附等温线及孔径分布曲线、(d)模拟晶体结构; (e) PA-TA-COF在1.0 A•g－1下400次的循环性能; (f) PA-TA-COF在不同电流密度下的倍率性能

Figure 9. (a) Synthesis, (b) PXRD pattern, (c) N2 adsorption-desorption isotherm and pore size distribution profile, (d) simulated structure of PA-TA-COF; (e) Cycling performance of PA-TA-COF at 1.0 A•g－1 for 400 cycles; (f) Rate capabilities of PA-TA COF at various current densities Copyright 2021, Springer Nature.

图10. PA-TA COF与TMC分子间化学反应示意图

图11. hcTPA-PZ COF的(a)合成路线与(b)氮气吸附-脱附等温线及孔径分布曲线; hcTPA-PZ COF膜的(c)制备过程与(d)分离性能

Figure 11. (a) Synthesis and (b) N2 adsorption-desorption isotherm and pore size distribution profile of hcTPA-PZ COF; (c) Fabrication process and (d) separation performance of the hcTPA-PZ COF membrane Copyright 2026, American Chemical Society.

图12. KUF-3的(a)合成、(b) PXRD图谱与(c)氮气吸附-脱附等温线及孔径分布曲线

图13. (a) sTTA上转换过程的简化Jablonski图, 其中溶解的卟啉和聚合物悬浮液之间发生三重态-三重态能量转移(TTET), 聚合物骨架内的激子能量转移(EET), 以及纳入聚合物骨架的发射体单元之间发生三重态-三重态湮灭(TTA); (b)由受激发射体分子扩散驱动的溶液中上转换; (c)由聚合物骨架中发射体单元间EET驱动的固态上转换

Figure 13. (a) Simplified Jablonski diagram for the sTTA upconversion process with triplet-triplet energy transfer (TTET) occurring between dissolved porphyrin and polymer suspension, exciton energy transfer (EET) within the polymer framework, and triplet-triplet annihilation (TTA) occurring between emitter units incorporated into the polymer framework; (b) Upconversion in solution driven by the diffusion of excited emitter molecules; (c) Upconversion in solid state driven by the EET between emitter units in the polymeric network Copyright 2026, Wiley-VCH.

图14. KUF-2的(a)合成路线与(b) PXRD图谱

COF		Topology	Interlayer distance/Å			BET surface area/(m²•g^－1)		Pore size/Å		Application	Reference
Aminal-COF-1		cpi	6.06			1169		5.2/8.2		Sensing	[31,56,57]
Aminal-COF-2		cpi	6.60			1168		5.4/8.2		—	[31]
DD-COF		cpi	6.06			805.98		5.4/7.5		Fluorescence	[58]
Por-Aminal-COF		cpi	3.96			813.04		6.3/13.9		Photocatalysis	[63]
TPTA-Pz-COF		cpi	7.45			1470		10		Electrocatalysis	[32]
PA-TA COF	p-hcb			6.20	—		7.3		Battery membrane separation			[54,71]
hcTPA-PZ COF	p-hcb			6.20	842		6.2		Gas separation			[72]
KUF-3	p-hcb			6.23	1268		7.3		Gas separation			[73]
Ant-COF-H	p-hcb			4.74	363		—		Energy conversion			[75]
Ant-COF-OH	p-hcb			4.96	256		—		Energy conversion			[75]
KUF-2	hxl-a			6.12	1169		3.9/5.9		Gas separation			[73]

表1. 已报道的缩醛胺COF总结

Table 1. Summary of reported aminal-linked COFs

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