A general synthesis of macrocyclic pi-electron-acceptor systems.
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.
Department of Chemistry, University of Reading, Whiteknights, Reading, RG6 6AH, UK. h.m.colquhoun@rdg.ac.uk
Howard M
HM
Colquhoun
Barnaby W
BW
Greenland
Zhixue
Z
Zhu
John S
JS
Shaw
Christine J
CJ
Cardin
Stefano
S
Burattini
Joanne M
JM
Elliott
Subhadeep
S
Basu
Travis B
TB
Gasa
J Fraser
JF
Stoddart