Synthesis of triphenylene based macrocycles

Abstract

This thesis is concerned with the synthesis of large macrocyclic structures based on the triphenylene system. The eventual aim of the project was to use the macrocycles to bind saccharides in water.

The first stage was to suitably functionalise the triphenylene system to give a base unit to the macrocycles. The first macrocycle (100) was built onto the base unit and obtained by cyclisation under high dilution conditions in very good yield as two isomers which could be separated by HPLC. Binding studies showed that a simple aromatic guest (1,3,5-benzene triol) would bind to the macrocycle in organic solvents.

In an attempt to make the macrocycle water soluble, a second version (101) was synthesised where the pentyl chains of 100 had been replaced by benzyl groups which could be removed after cyclisation and replaced the more hydrophilic groups.

Problems with the cyclisation of 101 and it's poor solubility in organic solvents leads to the development of a third macrocycle with methyl ester side-chains (118a). Hydrolysis of the methyl esters of 118a gave a water soluble derivative (118a) which was studied for binding interactions with a range of saccharides and other organic molecules but no binding was observed. (Fig. 11532)

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