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A diatropic ring current in a fluorofullerene trannulene
Glenn A Burley1, Patrick W Fowler, Alessandro Soncini
1University of Sussex, School of Chemistry, Physics & Environmental Science, Brighton, UK BN1 9Q.
Chemical Communications (Cambridge, England)
|January 6, 2004
Summary
This study reveals that a fluorofullerene derivative exhibits aromaticity, similar to classical annulenes. Its electronic structure shows a dominant ring current from four electrons in the highest occupied molecular orbital.
Area of Science:
- Organic Chemistry
- Computational Chemistry
- Materials Science
Background:
- Fullerenes are carbon-based molecules with unique electronic properties.
- Fluorinated fullerenes offer tunable characteristics for advanced applications.
- Understanding aromaticity in fullerene derivatives is key to predicting their behavior.
Purpose of the Study:
- To investigate the aromatic character of a specific fluorofullerene derivative, C60F15H3.
- To model the electronic structure and bonding in a system mimicking an experimentally characterized compound.
- To explore the contribution of electrons to observed ring currents.
Main Methods:
- Computational modeling using ipsocentric current-density maps.
- Analysis of the electronic structure, focusing on the highest occupied molecular orbital (HOMO).
- Comparison with classical aromatic systems like [18]trans-annulene.
Main Results:
- The fluorofullerene derivative C60F15H3 displays a significant diamagnetic ring current.
- This current is primarily driven by the four electrons in the highest occupied molecular orbital (HOMO).
- The electronic behavior resembles that of a (4n + 2) aromatic annulene.
Conclusions:
- The studied fluorofullerene derivative exhibits aromatic properties.
- The electronic delocalization, particularly from the HOMO, is crucial for this aromaticity.
- Computational current-density mapping is a valuable tool for assessing aromaticity in complex organic molecules.