Abstract
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 language | English (US) |
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Pages (from-to) | 5238-5241 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 11 |
Issue number | 22 |
DOIs | |
State | Published - 2009 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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CCDC 762943: Experimental Crystal Structure Determination
Colquhoun, H. M. (Creator), Greenland, B. W. (Creator), Zhu, Z. (Creator), Shaw, J. S. (Creator), Cardin, C. J. (Creator), Burattini, S. (Creator), Elliott, J. M. (Creator), Basu, S. (Creator), Gasa, T. B. (Creator), Stoddart, J. F. (Creator), Shaw, J. S. (Creator) & Basu, S. (Creator), Cambridge Crystallographic Data Centre, 2010
DOI: 10.5517/cctlx2c, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cctlx2c&sid=DataCite
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