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Synthesis of Ex(n)Box cyclophanes.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2013 Dec 06; Vol. 78 (23), pp. 11962-9. Date of Electronic Publication: 2013 Nov 07. - Publication Year :
- 2013
-
Abstract
- A rapid and efficient synthesis of the extended bipyridinium-based class of cyclophanes--that is, Ex(n)Box(4+) (n = 0-3), where n is the number of p-phenylene rings inserted between the pyridinium rings--is demonstrated, resulting in much higher yields of products along with a reduced output of oligomeric byproducts. Although each cyclophane can be synthesized readily without the use of a precise stoichiometric amount of template, ExBox(4+) can be prepared in 66% yield (following crystallization) using six equivalents of pyrene in a template-directed protocol. This new methodology has been employed to synthesize, in modest yield, a nearly 2.5 nm long cyclophane consisting of 12 aromatic rings.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 78
- Issue :
- 23
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 24128112
- Full Text :
- https://doi.org/10.1021/jo401993n