The selective functionalisation and difunctionalisation of p-substituted calix[6]arene and calix[8]arenes using hydrophilic moieties |
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Authors: | Hervé Gwénaëlle Hahn Dirk Uwe Hervé Anne-Cécile Goodworth Kerry J Hill Alison M Hailes Helen C |
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Institution: | Department of Chemistry, University College London, 20 Gordon Street, London, UK WC1H 0AJ. |
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Abstract: | 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. |
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