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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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Non-IPR Chlorofullerenes Obtained from IPR C₆₀ by Stone-Wales Rearrangements, ^#1809C₆₀Cl₁₀ and ^#1806C₆₀Cl₂₆

Nadezhda B Tamm¹, Natalia S Lukonina¹, Vladislav P Shakhov¹

¹Chemistry Department, Moscow State University, Leninskie gory, 119991 Moscow, Russia.

Inorganic Chemistry

|January 9, 2026

Summary

High-temperature chlorination of fullerene C60 induces Stone-Wales rearrangements, yielding novel non-isolated pentagon rule (non-IPR) chlorofullerenes like C60Cl10 and C60Cl26.

Area of Science:

Fullerenes chemistry
Organic synthesis
Materials science

Background:

Isolated pentagon rule (IPR) fullerenes possess unique cage structures.
Chlorination is a common method for functionalizing fullerenes.
Understanding fullerene isomerism is crucial for developing new materials.

Purpose of the Study:

To investigate the high-temperature chlorination of IPR-fullerene C60.
To characterize the resulting non-IPR chlorofullerene products.
To compare the chlorination patterns with known derivatives.

Main Methods:

High-temperature chlorination using antimony chlorides.
Isolation and purification of crystalline products.
Single-crystal X-ray diffraction (XRD) analysis.

Main Results:

Chlorination at 320 °C and 500 °C promoted Stone-Wales rearrangements.
Novel non-IPR chlorofullerenes, C60Cl10 (ca. 15% yield) and C60Cl26, were synthesized.
XRD analysis revealed specific chlorination patterns and fused pentagon structures in the non-IPR cages.

Conclusions:

High-temperature chlorination is an effective route to non-IPR fullerene derivatives.
The study elucidates the structural diversity achievable through fullerene functionalization.
Comparison with Cl and CF3 derivatives highlights structure-property relationships.

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