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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Planarized triarylboranes: stabilization by structural constraint and their plane-to-bowl conversion
Zhiguo Zhou1, Atsushi Wakamiya, Tomokatsu Kushida
1Department of Chemistry, Graduate School of Science, Nagoya University and JST-CREST, Furo, Chikusa, Nagoya 464-8602, Japan.
Journal of the American Chemical Society
|February 29, 2012
Summary
New triphenylborane compounds, synthesized via Friedel-Crafts cyclization, exhibit remarkable stability and unique electronic properties. These molecules undergo a controlled shape change upon fluoride ion treatment, offering potential applications in materials science.
Area of Science:
- Organoboron Chemistry
- Organic Synthesis
- Materials Science
Background:
- Triphenylborane derivatives are known for their unique electronic and photophysical properties.
- Controlling the molecular geometry of organoboron compounds is crucial for tuning their characteristics.
Purpose of the Study:
- To synthesize novel triphenylborane and diboraanthracene derivatives with constrained planar arrangements.
- To investigate the stability and properties of these new compounds.
- To explore their response to external stimuli, specifically fluoride ions.
Main Methods:
- Intramolecular multi-fold Friedel-Crafts cyclization for synthesis.
- Characterization of structural, electronic, and photophysical properties.
- Fluoride ion treatment to induce conformational changes.
Main Results:
- Successful synthesis of planar triphenylborane and diboraanthracene compounds.
- Demonstrated stability towards air, water, and amines.
- Observed characteristic electronic and photophysical behaviors.
- Achieved controlled plane-to-bowl conversion upon fluoride ion addition.
Conclusions:
- The synthesized compounds possess inherent stability and tunable properties.
- The facile plane-to-bowl conversion offers a novel mechanism for molecular switching.
- These findings contribute to the development of advanced organoboron materials.
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