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Azaindenocorannulenes: Synthesis, Properties, and Chirality
Xiaoqi Tian1, Loïc M Roch2, Nicolas Vanthuyne3
1Health Science Platform , Tianjin University , 92 Weijin Road , Nankai District, Tianjin 300072 , P. R. China.
Organic Letters
|April 18, 2019
Summary
Researchers synthesized bowl-shaped azaindenocorannulenes using palladium catalysis. These novel molecular bowls exhibit high configurational stability, surpassing that of common chiral molecules.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
- Materials Science
Background:
- Molecular bowls are intriguing structures with potential applications in various fields.
- Controlling the shape and stability of these bowls is crucial for their function.
- Azaindenocorannulenes represent a novel class of bowl-shaped molecules.
Purpose of the Study:
- To synthesize novel bowl-shaped azaindenocorannulenes.
- To investigate the structural, electronic, and configurational properties of these molecules.
- To establish structure-property relationships for molecular bowls.
Main Methods:
- Palladium-catalyzed intramolecular arylation for synthesis.
- X-ray crystallography for structural analysis.
- Cyclic voltammetry to determine reduction potentials.
- Vibrational Circular Dichroism (VCD) and Electronic Circular Dichroism (ECD) spectroscopy for configuration analysis.
Main Results:
- Successfully synthesized bowl-shaped azaindenocorannulenes 7-9.
- Observed bowl-in-bowl columnar stacking in crystalline compound 8.
- Developed a substituent model to explain reduction potentials of related molecular bowls.
- Correlated absolute configurations of bowls 7 and 9 with VCD and ECD spectra.
- Determined a high bowl inversion barrier for compound 9 (>190 kJ/mol), indicating significant configurational stability.
Conclusions:
- Palladium-catalyzed arylation is effective for creating complex bowl-shaped azaindenocorannulenes.
- These molecular bowls exhibit unique stacking behavior and predictable electronic properties.
- The synthesized bowls demonstrate exceptional configurational stability, exceeding that of known chiral systems like helicenes.
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