Corannulenes with Electron‐Withdrawing Substituents: Synthetic Approaches and Resulting Structural and Electronic Properties.

Corannulene is a multifaceted polyaromatic compound. It has many interesting properties; for example, it has a bowl‐shaped molecular structure that, in addition, undergoes a dynamic inversion process. It has attracted much attention within the last decades. This is not only due to its structural properties but also its electronic properties and its various potential applications to materials chemistry. Here, synthetic approaches towards corannulene derivatives with electron‐withdrawing substituents are summarized. This includes both selective and unselective methods. Further, the electrochemical properties, that is, the reduction potentials, are analyzed and compared. As a main conclusion, one can state that the electron affinity depends roughly linearly on the number of substituents. Finally, the structural behavior of the substituted buckybowls in the solid state is highlighted. This also allows a general statement about the influence of the electronic and steric nature of substituents on the molecular structures and the solid‐state packing of the corannulene derivatives. Bowled over: This review summarizes synthetic approaches towards corannulenes with electron‐withdrawing substituents. The article is focused on the introduction of perfluoroalkyl substituents. Recent advances on other functional groups are discussed in detail. The solid‐state structures and the electrochemical properties of the compounds are compared. [ABSTRACT FROM AUTHOR]