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 a bowl-shaped molecular structure which in addition undergoes a dynamic inversion process. It gained a lot of attraction within the last decades. This is not only due to its structural, but also its electronic properties and finally its various potential applications in materials chemistry. Herein, we summarize on the synthetic approaches towards corannulene derivatives with electron-withdrawing substituents. This includes both, selective and unselective methods. Further, the electrochemical properties, i. e. the reduction potentials are analysed and compared. As a main conclusion, one can state, that the electron affinity depends roughly linearly on the number of substituents. Finally, the structural behaviour of the substituted buckybowls in the solid state are 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.