Synthesis and supramolecular properties of a novel octaphosphonate porphyrin

Two complementary routes were developed for preparing novel octaphosphonate porphyrins. The use of protected/deprotected phosphonate-substituted precursors in the rational synthesis gave an overall yield 16%. A more streamlined synthetic path gave 21% overall yield of the target molecule. Octaphosphonate porphyrin possesses promising properties in supramolecular aggregate formation with cyclam. Cofacial reversible self-assembly of a meso-substituted octaphosphonate porphyrin with cyclam yields micrometer-long nanowires with a height of about 1-1.5 nm. The resulting wires were characterized by UV/Vis absorption, emission and atomic force microscopy and transmission electron microscopy.