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Multiply exo-Methylated Corannulenes.

Kazuhira Miwa¹, Shinobu Aoyagi¹, Toru Amaya¹

¹Department of Information and Basic Science, Graduate School of Science, Nagoya City University, Nagoya, 467-8501, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|September 15, 2023

Summary

Researchers synthesized multiply exo-methylated corannulenes, a novel class of organic molecules, using a reduction and methylation process. This work expands the toolkit for creating complex polycyclic aromatic hydrocarbons.

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Area of Science:

Organic Chemistry
Materials Science

Background:

Corannulene is a well-known polycyclic aromatic hydrocarbon with a unique bowl-shaped structure.
Functionalization of corannulene is crucial for developing new materials with tailored properties.

Purpose of the Study:

To develop a novel synthetic route for multiply exo-methylated corannulenes.
To explore the chemical reactivity of corannulene anions.

Main Methods:

Reduction of corannulene using sodium to generate anionic species.
Methylation of anionic corannulenes using dimethyl sulfate.

Main Results:

Successful synthesis of multiply exo-methylated corannulenes.
Demonstration of selective methylation at the exo-positions of the corannulene core.
The synthesized compounds exhibit unique structural and electronic properties.

Conclusions:

The developed method provides access to a new class of functionalized corannulene derivatives.
Multiply exo-methylated corannulenes hold potential for applications in organic electronics and supramolecular chemistry.