A general synthesis of macrocyclic π-electron-acceptor systems

Colquhoun, Howard. M, Greenland, Barnaby W, Zhu, Zhixue, Shaw, John S, Cardin, Christine J, Burattini, Stefano, Elliott, Joanne M, Basu, Subhadeep, Gasa, Travis B and Stoddart, J Fraser (2009) A general synthesis of macrocyclic π-electron-acceptor systems. Organic Letters, 11 (22). pp. 5238-5241. ISSN 1523-7060

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

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry
Depositing User: Barnaby Greenland
Date Deposited: 20 Apr 2018 07:40
Last Modified: 20 Apr 2018 07:40
URI: http://srodev.sussex.ac.uk/id/eprint/75259

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