Chemical Research in Chinese Universities ›› 2023, Vol. 39 ›› Issue (2): 161-169.doi: 10.1007/s40242-023-2363-3

• Review • Previous Articles     Next Articles

Progress of Indeno-type Organic Diradicaloids

GUO Jiaxiang, TIAN Xinyu, WANG Yue, DOU Chuandong   

  1. State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, P. R. China
  • Received:2022-12-30 Online:2023-04-01 Published:2023-03-16
  • Contact: DOU Chuandong E-mail:chuandong@jlu.edu.cn
  • Supported by:
    This work was supported by the National Natural Science Foundation of China (No. 22175074) and the Jilin Scientific and Technological Development Program, China(No. 20220101054JC).

Abstract: Organic diradicaloids have unusual open-shell nature and properties and are promising materials for organic electronics, spintronics, energy storage and nonlinear optics. In this review, we focus on indeno-type organic diradicaloids and summarize their molecular design and synthesis, as well as topological structures, open-shell characters and diradical properties. The molecular systems are classified into indenofluorenes and diindenoacenes, indeno-based molecules with one-dimensional, two-dimensional and unique topological structures, and heterocyclic indeno-based molecules. By constructing these various topological π-skeletons with tunable conjugation modes and variation of atomic composition, their key open-shell parameters, such as diradical characters and singlet-triplet energy gaps, along with the optical, electronic and magnetic properties, as well as stabilities are efficiently modulated. More attention may be paid to accurate computational analysis, rational design and synthesis, and novel functions of indeno-type diradicaloids, which will promote the development of radical chemistry and materials.

Key words: Polycyclic hydrocarbon, Open shell, Quinoidal conjugation, Diradical character, Antiaromaticity