A general synthesis of macrocyclic p-electron-acceptor systems
journal contribution
posted on 2023-06-09, 12:57authored byHoward. M Colquhoun, Barnaby GreenlandBarnaby Greenland, Zhixue Zhu, John S Shaw, Christine J Cardin, Stefano Burattini, Joanne M Elliott, Subhadeep Basu, Travis B Gasa, J Fraser Stoddart
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 p-donor arenes, and NMR studies in solution indeed confirm binding to 1,5-bis[hydroxy(ethoxy)ethoxy]naphthalene.