266994-71-2Relevant academic research and scientific papers
Bis-porphyrin arrays. Part 2. The synthesis of asymmetrically substituted bis-porphyrins
Beavington, Richard,Burn, Paul L.
, p. 605 - 609 (2008/10/08)
A strategy for the synthesis of asymmetrically substituted tetraazaanthracene linked bis-porphyrins in which the two porphyrin rings contain differences in their peripheral substituents has been developed. The method is illustrated by the preparation of bis-porphyrins with a single meso-halophenyl and seven meso-3,5-di-tert-butylphenyl substituents. The bis-porphyrins were prepared by condensation of a porphyrin-α-dione with benzene-1,2,4,5-tetraamine to form a porphyrin diaminoquinoxaline intermediate which was subsequently condensed with a second different porphyrin-α-dione. The key issue in the synthesis was the separation of the desired asymmetrically substituted bis-porphyrin from the symmetric bis-porphyrin by-products of similar polarities. Enhanced separation of the bis-porphyrin products was achieved by chelation of a metal into one of the porphyrin rings, the metal being introduced at the porphyrin-α-dione stage. Copper was successfully used when chelated into the less polar porphyrin-α-dione but the use of zinc in the more polar porphyrin-α-dione to enhance bis-porphyrin separation was unsuccessful as the pyridinium hydrochloride produced in the reaction was found to demetallate the porphyrins.
Rigid, Laterally-bridged Bis-porphyrin Systems
Crossley, Maxwell J.,Burn, Paul L.
, p. 39 - 40 (2007/10/02)
The synthesis of novel bis-porphyrin systems in which the porphyrins are rigidly constrained in a coplanar arrangement is reported.
