Modular Synthesis of a Semibuckminsterfullerene
Cody F Dickinson1, Justin K Yang1, Glenn P A Yap2
1Chemistry Department, University of Hawaii at Manoa, Honolulu, Hawaii 96822, United States.
Organic Letters
|July 12, 2022
Summary
Researchers developed a modular synthesis for preparing complex polycyclic aromatic hydrocarbons, including a novel tetrabromosemibuckminsterfullerene. This method uses common reagents and avoids high temperatures, simplifying the creation of unsymmetrical molecules.
Area of Science:
- Organic Chemistry
- Materials Science
- Fullerene Chemistry
Background:
- Dibenzochrysenes and diindenochrysenes are complex polycyclic aromatic hydrocarbons with unique electronic properties.
- Previous synthetic routes often lack modularity or require harsh conditions.
- The development of efficient and versatile synthetic strategies is crucial for accessing novel fullerene derivatives.
Purpose of the Study:
- To develop a modular and efficient convergent synthesis for dibenzochrysenes and diindenochrysenes.
- To prepare a specific semibuckminsterfullerene derivative, 5,6,11,12-tetrabromosemibuckminsterfullerene.
- To establish a generalizable method for synthesizing unsymmetrical semibuckminsterfullerenes.
Main Methods:
- Convergent synthesis utilizing difluorofluorenes and acetoxyenone 15.
- Employing an unsymmetrical intermediate to control regiochemistry.
- Utilizing common reagents and nonpyrolytic conditions.
Main Results:
- Successful synthesis of dibenzochrysenes and diindenochrysenes.
- Preparation of 5,6,11,12-tetrabromosemibuckminsterfullerene (31).
- Demonstration of a highly modular synthetic approach.
Conclusions:
- The developed synthesis is modular and efficient for constructing complex polycyclic aromatic hydrocarbons.
- This method enables the straightforward preparation of semibuckminsterfullerenes from unsymmetrical diindenochrysenes.
- The approach avoids pyrolytic conditions and utilizes readily available reagents, making it broadly applicable.
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