TY - JOUR
T1 - A general synthesis of macrocyclic π-electron-acceptor systems
AU - Colquhoun, Howard M.
AU - Greenland, Barnaby W.
AU - Zhu, Zhixue
AU - Shaw, John S.
AU - Cardin, Christine J.
AU - Burattini, Stefano
AU - Elliott, Joanne M.
AU - Basu, Subhadeep
AU - Gasa, Travis B.
AU - Stoddart, J. Fraser
PY - 2009
Y1 - 2009
N2 - 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.
AB - 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.
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U2 - 10.1021/ol9021782
DO - 10.1021/ol9021782
M3 - Article
C2 - 19860397
AN - SCOPUS:70749136440
VL - 11
SP - 5238
EP - 5241
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 22
ER -