The synthesis and
purification of water-soluble porphyrin-type
compounds for photodynamic therapy and other medical applications
is often a tedious exercise. Here, we have investigated the simple
stratagem of adding a water-soluble axial ligand to the standard protocol
for iridium insertion into simple
meso
-triarylcorroles.
Early results showed that six-coordinate Ir[T
p
XPC](dna)
2
derivatives, in which T
p
XPC = tris(
para
-X-phenyl)corrole (X = CF
3
, CN, H, and OMe)
and dna = dinicotinic acid, are highly water-soluble. In the end,
however, all axially nitrogen-ligated complexes proved unstable with
respect to chromatographic purification and storage. Five-coordinate
water-soluble phosphine adducts, fortunately, proved a great improvement.
From the point of view of ease of purification and storage, the best
products proved to be Ir[T
p
XPC](L), where X = CF
3
and OMe and L = tris(2-carboxyethyl)phosphine (tcep) and
trisodium tris(3-sulfonatophenyl)phosphine (tppts); carefully optimized
synthetic protocols are presented for these four compounds.