A general synthesis of macrocyclic π-electron-acceptor systems

Howard M. Colquhoun, Barnaby W. Greenland, Zhixue Zhu, John S. Shaw, Christine J. Cardin, Stefano Burattini, Joanne M. Elliott, Subhadeep Basu, Travis B. Gasa, J. Fraser Stoddart

Research output: Contribution to journalArticlepeer-review

20 Scopus citations


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 .T-donor arenes, and NMR studies in solution indeed confirm binding to 1,5-bis[hydroxy(ethoxy)ethoxy] naphthalene.

Original languageEnglish (US)
Pages (from-to)5238-5241
Number of pages4
JournalOrganic Letters
Issue number22
StatePublished - 2009

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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