A new method for facile solubilization and transformation of nanocarbons

April 23, 2025

Expected to applications in organic luminescent materials and fluorescent labels for bioimaging

A joint research group consisting of researchers from Nagoya University, the RIKEN PRI and the RIKEN CSRS has successfully developed a new method for the efficient solubilization and transformation of polycyclic aromatic hydrocarbons (PAHs), a type of nanocarbon known for its poor solubility in organic solvents.

PAHs are organic compounds abundantly found in nature, consisting mainly of fused benzene rings. Although PAHs are used in various fields, their planar structure and strong intermolecular interactions limit their solubility in both water and organic solvents. These characteristics have posed significant challenges for their chemical modification and practical applications. In this study, the researchers developed a method for introducing a "high solubility sulfonium group" and successfully synthesized novel, highly soluble diaryl sulfoxides bearing triethylene glycol side chains, which exhibit excellent solubility in both water and organic solvents. When these sulfoxides were reacted with PAHs under acidic conditions, the corresponding PAH sulfonium salts were obtained in good yields. Moreover, the high solubility of these salts in organic solvents enabled further functional group transformations and facilitated nanographene synthesis. This research presents a promising new strategy for the efficient transformation and solubilization of a wide range of PAHs, paving the way for broader applications not only in nanographene synthesis but also in diverse fields such as fluorescent labeling.

Original article: Chemical Science doi: 10.1039/d5sc01415h; J. E. Erchinger, T. Okumura, K. Nakata, D. Shimizu, C. G. Daniliuc, K. Amaike, F. Glorius, K. Itami, H. Ito,; "Functionalization and solubilization of polycyclic aromatic compounds by sulfoniumization".
Contact: Kenichiro Itami
Team Director
Expanded Chemical Space Research Team