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Updated: May 16, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Functionalization and solubilization of polycyclic aromatic compounds by sulfoniumization
Johannes E Erchinger1, Tsubasa Okumura2, Kanami Nakata2
1Organisch-Chemisches Institut, University of Münster Corrensstrasse 36 48149 Münster Germany.
Abstract:
Despite their unique physical properties and diverse applications in materials science, poor solubility of polycyclic aromatic hydrocarbons (PAHs) limits further fine-tuning and investigation of these systems. Herein, we report a sulfoniumization strategy to solubilize and functionalize a diverse range of PAHs in a one-step protocol using a triethylene glycol ether-substituted diaryl sulfoxide. While mono-sulfoniumization is generally observed, modification of the reaction conditions to favor bis-sulfoniumization is shown. The downstream applicability of the resulting PAH sulfonium salts is validated through a series of post-functionalization reactions that include C-C and C-heteroatom bond formation, while their application in annulative π-extension (APEX) is showcased by the synthesis of tetra-tert-butylquaterrylene from perylene. The red-shifted absorption and fluorescence, along with high water solubility of the PAH sulfonium salts, enable their application in bio-imaging, where they demonstrate selective mitochondrial staining without cytotoxicity.
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