The selective functionalisation and difunctionalisation of p-substituted calix[6]arene and calix[8]arenes using hydrophilic moieties.
Methodologies to access water soluble large ringed calixarenes in good yield using efficient synthetic procedures have been investigated. Symmetrical partial functionalisations at the lower rim are described using activated [n]ethylene glycol chains and the addition behaviour contrasted with that of bromoalkanenitriles which proceeds with no observed regioselectivity. Full functionalisations of the calixarenes bearing hydrophilic groups are then investigated and a two-step procedure established which appears to be generally applicable for the addition of different [n]ethylene glycol chains. Furthermore, difunctionalisation under different reaction conditions are described. Throughout, strategies for the characterisation of these high mass compounds are outlined.
Hervé
Gwénaëlle
G
Department of Chemistry, University College London, 20 Gordon Street, London, UK WC1H 0AJ.
Hahn
Dirk Uwe
DU
Hervé
Anne-Cécile
AC
Goodworth
Kerry J
KJ
Hill
Alison M
AM
Hailes
Helen C
HC