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Updated: Jul 11, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
1,4,5,8,9,12-Hexamethyltriphenylene. A molecule with a flipping twist
Yi Wang1, Andrew D Stretton, Mark C McConnell
1School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, U.K.
This study details the synthesis of hexamethyltriphenylene, revealing its distorted structure and dynamic conformational changes in solution. It also highlights its properties as a fluorescent blue emitter and its electrochemical oxidation behavior.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
- Materials Science
Background:
- Hindered aromatic compounds like triphenylenes exhibit unique structural and dynamic properties.
- Understanding conformational dynamics is crucial for designing molecules with specific optical and electronic characteristics.
Purpose of the Study:
- To synthesize and characterize 1,4,5,8,9,12-hexamethyltriphenylene (5).
- To investigate the solid-state and solution-state conformational dynamics of compound 5.
- To explore the photophysical and electrochemical properties of compound 5.
Main Methods:
- X-ray crystallography for solid-state structure determination.
- Variable-temperature 1H NMR spectroscopy for solution dynamics.
- Molecular modeling to elucidate conformational pathways.
- UV-Vis spectroscopy and fluorescence measurements for photophysical properties.
- Electrochemical techniques (e.g., cyclic voltammetry) for redox behavior.
Main Results:
- Compound 5 exhibits a highly distorted C2 geometry in the solid state with a significant end-to-end twist.
- Variable-temperature NMR and molecular modeling reveal rapid interconversion between C2 enantiomers and slower C2-D3 interconversion in solution.
- Compound 5 is a stable, fluorescent blue emitter.
- The compound undergoes irreversible one-electron oxidation to a radical cation with predicted C2 geometry and a 60-degree twist.
Conclusions:
- The study provides the first clear evidence of conformational interchange in hindered triphenylenes.
- 1,4,5,8,9,12-hexamethyltriphenylene (5) possesses interesting structural, dynamic, photophysical, and electrochemical properties.
- These findings contribute to the understanding of molecular dynamics and electronic properties in sterically encumbered aromatic systems.
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