Unprecedented C-F bond cleavage in perfluoronaphthalene during cobaltocene reduction

Area of Science:

• Organometallic Chemistry
• Fluorocarbon Chemistry
• Materials Science

Background:

• Perfluoronaphthalene is a highly fluorinated aromatic compound with strong carbon-fluorine (C-F) bonds.
• Activation of C-F bonds is crucial for synthesizing novel fluorinated organic and organometallic compounds.
• Silicon-based reagents offer unique reactivity for bond activation processes.

Purpose of the Study:

• To investigate the C-F bond activation of perfluoronaphthalene using a specific silicon reagent (5-SIDipp).
• To synthesize and characterize novel dicationic salts derived from perfluoronaphthalene.
• To explore the luminescent properties of the synthesized compounds and their potential applications.

Main Methods:

• Reaction of perfluoronaphthalene with 5-SIDipp to achieve C-F bond activation.
• Formation of dicationic salts with fluoride (HF2-) and heptafluorodiborate (B2F7-) counter-anions.
• Anion exchange reaction using tetrabutylammonium hexafluorophosphate (NBu4PF6) to obtain the hexafluorophosphate salt.
• In situ reaction with cobaltocene to study the formation of new cobalt species.

Main Results:

• Successful activation of C-F bonds in perfluoronaphthalene by 5-SIDipp, yielding dicationic salts.
• Synthesis of a highly luminescent dicationic hexafluorophosphate salt (3·2PF6) via anion exchange.
• Observation of a distinct cobalt(I) species upon in situ addition of cobaltocene.

Conclusions:

• 5-SIDipp is an effective reagent for the C-F bond activation of perfluoronaphthalene.
• The study demonstrates the synthesis of novel luminescent dicationic salts with potential applications in materials science.
• The reactivity of the system with cobaltocene opens avenues for exploring new organometallic cobalt chemistry.