Affiliation:
1. Department of Information and Basic Science Graduate School of Science Nagoya City University Nagoya 467-8501 Japan
2. Division of Chemistry Faculty of Pure and Applied Sciences and Tsukuba Research Center for Energy Materials Sciences (TREMS) University of Tsukuba 1-1-1 Tennodai Tsukuba 305-8571 Japan
3. Department of Chemistry Graduate School of Science Kyoto University Kyoto 606-8502 Japan
Abstract
AbstractThe curved π‐conjugated surface of bowl‐shaped corannulene has been multiply methylated to form exo‐di‐, ‐tetra‐, and ‐hexamethylated corannulenes. The multimethylations became possible through in‐situ iterative reduction/methylation sequences that involve the reduction of corannulenes using sodium to form the anionic corannulene species, and the subsequent SN2 reaction of the anionic species with reduction‐resistant dimethyl sulfate. X‐ray diffraction analyses, NMR, MS, UV‐Vis measurements, and DFT calculations have revealed the molecular structures of the multimethylated corannulenes and the sequence of the multimethylation. This work has the potential to contribute to the controlled synthesis and characterizations of multifunctionalized fullerenes.
Funder
Core Research for Evolutional Science and Technology
Japan Society for the Promotion of Science
Subject
General Chemistry,Catalysis,Organic Chemistry