Schiff base calixarenes

• Main Author: Jensen, Svend Borup
• Published: University of the West of Scotland 2002
• Subjects: 547; Butylcalixarenes
• Online Access: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.246345

Four different synthetic routes to the sub-target, the p-tert-butylcalix[4lethylamine (6a) from thep-tert-butylcalix[4]arene (1a) have been examined. The best one was a 5-step synthesis, which gave an overall yield of65%. p-tert-Butylcalix[6]ethylamine (6b) and p-tert-butylcalix[8]ethylamine (6c) were synthesised from their respective p-tertbutylcalixarenes by the same route as the p-tert-butylcalix[4]ethylamine (6a). The three different amines (compound (6a), (6b) and (6c)) were used in 14 different Schiff -base type reactions which resulted in six Schiff-base compounds which were fully characterised by NMR, IR, FAB-ms and UV-vis. Insertion studies of the Schiff-base compounds along with template synthesis of the Schiff-base compounds were also attempted. The uptake of solid metal salt by the Schiff-base compounds in solution was examined by UV-vis spectroscopy. One of the Schiff -base compounds synthesised was the ferrocenecarboxaldehyde Schiff-base calix[4]arene (22a). An electrochemical analysis of this compound was undertaken to assess whether if it could be used as a sensor for metal ions. Molecular modelling of the Schiff-base compound and a crystal structure ofp-tert-butylcalix[4]ethylnitrile (8) are also presented in the thesis