A General Synthesis of Macrocyclic pi-Electron-Acceptor Systems

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Cyclocondensations of aromatic diamines with 1,1'-bis(2,4-dinitrophenyl)-4,4'-bipyridinium salts afford doubly or quadruply charged, macrocyclic, N,N'-diarylbipyridinium cations. These are tolerant of a wide range of acids, bases, and nucleophiles, although they appear to undergo reversible, one-electron reduction by tertiary amines. Single-crystal X-ray analysis demonstrates the presence of a macrocycle conformation In which the 4,4'-bipyridinium and 4,4'-biphenylenedisulfonyl residues are suitably spaced and aligned for complexation with pi-donor arenes, and NMR studies in solution indeed confirm binding to 1,5-bis[hydroxy(ethoxy)ethoxy]naphthalene.
Publisher
AMER CHEMICAL SOC
Issue Date
2009-11
Language
English
Article Type
Article
Keywords

SEQUENCE INFORMATION; RECOGNITION; HOSTS

Citation

ORGANIC LETTERS, v.11, no.22, pp.5238 - 5241

ISSN
1523-7060
DOI
10.1021/ol9021782
URI
http://hdl.handle.net/10203/93999
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