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Stable (BIII -Subporphyrin-5-yl)dicyanomethyl Radicals
- Source :
- Chemistry - A European Journal. 25:1706-1710
- Publication Year :
- 2019
- Publisher :
- Wiley, 2019.
-
Abstract
- Stable BIII -subporphyrin-substituted dicyanomethyl radicals were synthesized by SN Ar reaction of meso-bromo- or meso-chlorosubporphyrins with malononitrile followed by oxidation with PbO2 . Different from previously reported dicyanomethyl radicals that underwent σ- or π-dimer formation both in the solid state and in solutions, subporphyrin-stabilized dicyanomethyl radicals exist as monomers in solutions even at low temperature. DFT calculations revealed efficient spin delocalization over the entire subporphyrin. In the solid state, these radicals form weak π-dimers with antiferromagnetic interactions depending on the crystal packing structures.
- Subjects :
- 010405 organic chemistry
Radical
Organic Chemistry
Solid-state
General Chemistry
010402 general chemistry
01 natural sciences
Catalysis
0104 chemical sciences
Crystal
chemistry.chemical_compound
Crystallography
Delocalized electron
Monomer
chemistry
Antiferromagnetism
Spin (physics)
Malononitrile
Subjects
Details
- ISSN :
- 09476539
- Volume :
- 25
- Database :
- OpenAIRE
- Journal :
- Chemistry - A European Journal
- Accession number :
- edsair.doi...........ff88f91e17ff1076536441ed099a857c