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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
A general synthesis of macrocyclic pi-electron-acceptor systems
Howard M Colquhoun1, Barnaby W Greenland, Zhixue Zhu
1Department of Chemistry, University of Reading, Whiteknights, Reading, RG6 6AH, UK. h.m.colquhoun@rdg.ac.uk
New macrocyclic N,N-diarylbipyridinium cations were synthesized. These stable compounds demonstrate potential for complexation with pi-donor arenes, confirmed by X-ray and NMR studies.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
- Materials Science
Background:
- Macrocyclic compounds offer unique structural and binding properties.
- Bipyridinium frameworks are known for their redox activity and potential in host-guest chemistry.
Purpose of the Study:
- To synthesize novel doubly or quadruply charged, macrocyclic, N,N'-diarylbipyridinium cations.
- To investigate the stability and structural characteristics of these new macrocycles.
- To explore their potential for complexation with pi-donor arenes.
Main Methods:
- Cyclocondensation reactions of aromatic diamines with 1,1'-bis(2,4-dinitrophenyl)-4,4'-bipyridinium salts.
- Single-crystal X-ray diffraction analysis to determine macrocycle conformation.
- Nuclear Magnetic Resonance (NMR) spectroscopy to confirm binding interactions in solution.
Main Results:
- Successfully synthesized doubly or quadruply charged, macrocyclic, N,N'-diarylbipyridinium cations.
- These cations exhibit stability towards a wide range of acids, bases, and nucleophiles.
- X-ray analysis revealed a conformation suitable for pi-arene complexation, which was confirmed by NMR studies with 1,5-bis[hydroxy(ethoxy)ethoxy]naphthalene.
Conclusions:
- The synthesized macrocyclic N,N'-diarylbipyridinium cations are robust and possess a defined conformation for host-guest interactions.
- These compounds show promise for applications in supramolecular chemistry and materials science, particularly in recognizing and binding pi-donor molecules.
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