A general synthesis of macrocyclic pi-electron-acceptor systemsColquhoun, H.M., Greenland, B.W., Zhu, Z.X., Shaw, J.S., Cardin, C.J. ORCID: https://orcid.org/0000-0002-2556-9995, Burattini, S., Elliott, J.M. ORCID: https://orcid.org/0000-0001-7469-4154, Basu, S., Gasa, T.B. and Stoddart, J.F. (2009) A general synthesis of macrocyclic pi-electron-acceptor systems. Organic Letters, 11 (22). pp. 5238-5241. ISSN 1523-7052 Full text not archived in this repository. It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing. To link to this item DOI: 10.1021/ol9021782 Abstract/SummaryCyclocondensations 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.
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