Soluble polymer supported synthesis of a monosubstituted tetraaryl porphyrin
A new synthesis of monosubstituted tetraarylporphines is described based upon the soluble polymer supported synthesis strategy. Low molecular weight poly(ethylene glycol) is chloromethylated at both ends. These ends are then used to build up the polymer-bound ether of 5-(4′-hydroxymethyl)-10,15,20-tritolylporphine, which, after purification of the polymer, can be cleaved in high yield with TiCl4. While the method offers useful conveniences, such as the ease of separation and purification of the desired material, the overall yield is low: 100 mg from 40 g of polymer. Oligomerization of the polymer during chloromethylation increases the polymer molecular weight and thereby decreases the number of end groups per gram of polymer. Keywords: porphyrin, tetraaryl, monosubstituted poly(ethylene glycol) oligomerization, polymer-supported synthesis.