Soluble phtalocyanines and related compounds

• Main Author: Shuttleworth, Leslie
• Published: University of Surrey 1967
• Online Access: https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.751686

The preparation of a number of soluble derivatives of phthalocyanine has been carried out. These derivatives have been used to study the aromatic ring by proton magnetic resonance spectroscopy. From the results of these studies some conclusions have been made concerning the structure and aromatioity of the phthalooyanine macrocycle. Specific studies have been carried out on dialkoxy-silicon-phthalocyanines and some evidence has been put forward for the structure of these compounds from proton magnetic resonance studies. Deuteration has been used as a technique to elucidate some ambiguous features of the P.M.R. spectra. Tetra -alkyl -phthalocyanines have been prepared from alkyl substituted intermediates and have been found to have enhanced solubility in chloroform. Proton magnetic resonance studies indicated that molecular aggregation occurred in concentrated solution. It has been shown that aggregation is inhibited by substituents in the 5 and 6 co-ordinate positions attached to the central metal and P.M.R. studies on these compounds have proved to be of interest: in particular, di-alkoxy-silicon-tetrakis(4-t-butyl)-phthalocyanines have been examined. Some suggestions have been made as to the effect of substituents upon the atomaticity of the macrocycle. Peripheral substitution of t-butyl groups has been suggested as a suitable general method for solubilising the macrocycle for P. M. R. studies. In this way, the structure of bis(phthalocyanine)---tin has been investigated and some new evidence for the structure of this compound is presented. Finally, chemical shifts were used to calculate the aromaticity of the macrocycle, and the results of these calculations are discussed.