A New Type of Calixarene: Octahydroxypyridine[4]arenes

✍ Scribed by Thorsten Gerkensmeier; Jochen Mattay; Christian Näther

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 333 KB
• Volume: 7
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/1521-3765(20010119)7:2<465::aid-chem465>3.0.co;2-a

✦ Synopsis

A new type of calixarene has been synthesised. Like resorcinol and a number of resorcinol derivatives, 2,6-dihydroxypyridine has been proven to form cyclic tetramers in moderate yields with a number of aliphatic and two aromatic aldehydes in acidic media. The problem of the formation of configurational isomers can be reduced by increasing the reaction temperature and time. With electron-rich aromatic aldehydes, 2,6-dihydroxypyridine unexpectedly yields deep-coloured acyclic quinoid systems. The octahydroxypyridine [4]arenes may have a high potential as receptors for molecular recognition and self organisation.