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Stable N,N'-Diarylated Dihydrodiazaacene Radical Cations
Gaozhan Xie1, N Maximilian Bojanowski1, Victor Brosius1
1Organisch-Chemisches Institut, Ruprecht-Karls Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 23, 2020
Summary
Stable N,N'-diarylated dihydroazaacene radical cations were synthesized and studied. These novel radical cations exhibit remarkable stability, remaining unchanged for over 24 hours under ambient conditions.
Area of Science:
- Organic Chemistry
- Materials Science
- Photochemistry
Background:
- Dihydroazaacenes are a class of organic compounds with potential applications in materials science.
- Stable radical cations are valuable intermediates in organic synthesis and electronic materials.
Purpose of the Study:
- To synthesize novel N,N"-diarylated dihydroazaacene radical cations.
- To investigate the stability and properties of these radical cations.
- To explore their potential applications in electronic materials.
Main Methods:
- Palladium-catalyzed Buchwald-Hartwig amination for synthesis of neutral precursors.
- Oxidation of neutral dihydroazaacenes to form radical cations.
- UV-vis spectroscopy, single crystal X-ray diffraction, and Density Functional Theory (DFT) calculations for characterization.
Main Results:
- Successfully synthesized three stable N,N -diarylated dihydroazaacene radical cations.
- Characterized both neutral and oxidized species using spectroscopic and crystallographic methods.
- DFT calculations provided insights into the electronic structure and stability.
- Demonstrated remarkable stability of the radical cations in dichloromethane solution for over 24 hours at ambient conditions.
Conclusions:
- N,N -diarylated dihydroazaacene radical cations can be synthesized with high stability.
- These compounds represent a promising new class of stable organic radical cations.
- Their stability suggests potential for applications in organic electronics and redox-active materials.
Keywords:
DFT calculationsN,N’-diaryldiazaacenesUV/Vis spectroscopyradical cationsingle crystal structureMore Related Videos
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