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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Monometallic Endohedral Azafullerene
Wenhao Xiang1, Xiaole Jiang1, Yang-Rong Yao1
1Department of Materials Science and Engineering, CAS Key Laboratory of Materials for Energy Conversion, Anhui Laboratory of Advanced Photon Science and Technology, University of Science and Technology of China, Hefei 230026, China.
Researchers synthesized the first pristine monometallic endohedral azafullerene (MEAF), La@C81N, after a 20-year challenge. This breakthrough offers new insights into fullerene skeletal modifications and properties.
Area of Science:
- Fullerene Chemistry
- Supramolecular Chemistry
- Materials Science
Background:
- Azafullerenes, modified fullerenes with nitrogen atoms, alter fullerene properties.
- Monometallic endohedral azafullerenes (MEAFs) like La@C81N were previously only detected in ionized gas phases.
- The synthesis of pristine MEAFs remained a significant challenge for over two decades.
Purpose of the Study:
- To report the first successful synthesis, isolation, and characterization of pristine monometallic endohedral azafullerene (MEAF) La@C81N.
- To investigate the structural and electronic properties of this novel azafullerene.
- To provide new insights into the skeletal modification of fullerenes through nitrogen substitution.
Main Methods:
- Synthesis and isolation of La@C81N.
- Single-crystal X-ray diffraction for structural determination.
- Density Functional Theory (DFT) computations for electronic structure analysis.
Main Results:
- The first pristine MEAF, La@C81N, was successfully synthesized and characterized.
- X-ray diffraction revealed an 82-atom cage with pseudo C3(8) symmetry.
- DFT calculations indicated nitrogen substitution at a hexagon/hexagon/pentagon junction, distant from the La atom.
- La@C81N exhibits a stable, closed-shell electronic state, contrasting with the open-shell state of La@C82.
Conclusions:
- The synthesis of pristine La@C81N overcomes a long-standing challenge in fullerene chemistry.
- The structural and electronic properties of La@C81N differ significantly from its parent fullerene.
- This work opens new avenues for designing and synthesizing novel azafullerene derivatives with tailored properties.
