Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (3): 1000-1011.DOI: 10.6023/cjoc202211042 Previous Articles     Next Articles

Special Issue: 中国女科学家专辑



吴孔川, 卢铠洪, 林建斌*(), 张慧君*()   

  1. 厦门大学化学化工学院 厦门 361005
  • 收稿日期:2022-11-30 修回日期:2023-01-20 发布日期:2023-02-06
  • 通讯作者: 林建斌, 张慧君
  • 基金资助:
    国家自然科学基金(22171237); 国家自然科学基金(22271239); 国家自然科学基金(22071208); 厦门市青年创新基金(3502Z20206058)

Research Progress in Ortho-C—H Bond Functionalization of Rylene Diimides

Kongchuan Wu, Kaihong Lu, Jianbin Lin(), Huijun Zhang()   

  1. College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005
  • Received:2022-11-30 Revised:2023-01-20 Published:2023-02-06
  • Contact: Jianbin Lin, Huijun Zhang
  • Supported by:
    National Natural Science Foundation of China(22171237); National Natural Science Foundation of China(22271239); National Natural Science Foundation of China(22071208); Youth Innovation Foundation of Xiamen(3502Z20206058)

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