莱啉酰亚胺类化合物的邻位C—H键功能化研究进展

doi:10.6023/cjoc202211042

摘要/Abstract

莱啉酰亚胺是一类重要的功能有机染料. 独特的缺电性共轭骨架与优异的光电性质使其成为多环芳烃家族中的重要成员, 在有机场效应晶体管、有机光伏器件和生物医学传感等领域具有广阔的应用前景. 对莱啉酰亚胺骨架的精准修饰不仅可以有效调控分子能级, 还有利于实现分子间的可控组装, 是高效创制新型π-分子材料的有效手段. 早期, 受合成方法的限制, 莱啉酰亚胺骨架母核修饰的位点主要局限于电子云密度稍高的湾位, 但在该位点引入取代基会扭曲π-平面, 不利于π-分子之间的有效堆积. 莱啉酰亚胺骨架邻位选择性修饰不影响母核的平面性, 近年来受到广泛关注, 催生出系列莱啉酰亚胺邻位C—H键功能化的新策略. 根据成键类型不同, 以苝二酰亚胺和萘二酰亚胺为例, 系统总结了莱啉酰亚胺骨架邻位C—H键功能化的方法, 以及邻位修饰对莱啉骨架光电性质和组装的影响.

关键词: 莱啉酰亚胺, π-分子材料, C—H键活化, 过渡金属催化

Rylene diimides (RDIs) derivatives are an important class of functional organic dyes. With unique electron-defi- cient conjugated backbones and excellent photoelectronic properties, these polycyclic aromatic hydrocarbons have wide applications in organic field effect transistors, organic photovoltaic devices, and biomedical sensing. Precise modification of the RDIs skeletons can not only regulate molecular energy levels, but also facilitate controllable assembly between π-molecules, which is an effective means to create new π-molecular materials. In the early stage, due to the limitation of synthetic methods, only modifications on the bay positions of RDIs can be achieved. However, the introduction of substituents on these sites would distort the π-plane of RDIs and was not conducive to effective π-stacking between molecules. The selective modifications of RDIs skeletons on the ortho positions do not affect the planarity of the skeletons, which have received much attention in recent years, leading to a series of efficient strategies toward ortho-functionalized RDIs. The methods of ortho-C—H bond functionalization of RDIs such as perylene diimides and naphthalene diimides, and the influence of ortho- modification on the photoelectronic properties and assembly of RDIs derivatives are summarized.

Key words: rylene diimides, π-conjugated materials, C—H bond activation, transition metal catalysis

引用此文

吴孔川, 卢铠洪, 林建斌, 张慧君. 莱啉酰亚胺类化合物的邻位C—H键功能化研究进展[J]. 有机化学, 2023, 43(3): 1000-1011.

Kongchuan Wu, Kaihong Lu, Jianbin Lin, Huijun Zhang. Research Progress in Ortho-C—H Bond Functionalization of Rylene Diimides[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1000-1011.

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图/表 9

图1. 莱啉酰亚胺的化学结构及常见修饰位点(以PDI为例)

Figure 1. Chemical structures of rylene diimides and common modification sites (taking PDI as an example)

图2. 金属钌催化PDI邻位烷基化和芳基化反应[8-9]

Figure 2. Ruthenium-catalyzed ortho-alkylation and arylation of PDI[8-9]

图3. 金属钌或铑催化PDI邻位C—H键活化构建C—C键[10,12]

Figure 3. Ruthenium- or rhodium-catalyzed ortho C—H bond activation of PDI for direct C—C bond formation[10,12]

图4. 过渡金属催化的PDI邻位C—H硼酸酯化反应[15-16]

Figure 4. Transition metal-catalyzed ortho C—H bond boronization of PDI[15-16]

图5. 邻位卤代PDI的合成[18,21-22]

Figure 5. Synthesis of ortho-halogenated PDIs[18,21-22]

图6. (a, b) PDI邻位衍生化-基于PDI骨架的π-分子可控组装[24-25], 以及(c, d) PDI邻位增环-手性有机功能材料开发[11b,22,29b]

Figure 6. (a, b) Selective ortho-functionalization of PDI-controllable assembly of π-molecules based on PDI skeletons[24-25], and (c, d) selective ortho-π-extension of PDI-development of chiral functional materials[11b,22,29b]

图7. 二苯基膦锂试剂、氮杂环卡宾、格氏试剂与PDI的反应[30?-32]

Figure 7. Reactions of diphenylphosphine lithium, N-heterocyclic carbenes and Grignard reagent with PDI[30?-32]

图8. PDI的邻位胺化反应[33,35-36]

Figure 8. Selective ortho-amination reactions of PDI[33,35-36]

图9. NDI邻位C—H键功能化反应[34-35,39?-41]

Figure 9. Ortho C—H bond functionalization of NDI[34-35,39?-41]

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