Two aldehydes, 2,6-diacetamido-4-formylpyridine (7) and 1-butyl-6-formyluracil (11), are used to synthesize five pyridyl and four uracyl meso-subsituted porphyrins. With these complementary porphyrin building blocks, it is possible to build various types of multi-porphyrin supramolecules with different spatial relationships in predefined geometries. The formation and properties of self-complementary dimers and a closed tetrameric square are presented as a basis of comparison to the latter system in the solid state. An X-ray structure of 5,10-bis(4-tert-butylphenyl)-15,20-bis(3,5-diacetamido-4-pyridyl)porphyrin confirms its molecular structure and reveals a hydrogen-bonded supramolecular organization mediated by water molecules.
Discrete squares and tapes of porphyrins are self-assembled by self-complementary hydrogen bonding between diacetamidopyridyl recognition groups rigidly linked to the chromophore.
Porphyrins bearing uracyl motifs at the four meso positions self-organize via homo-complementary hydrogen bonds and π-stacking into nanofibers, nanorods and thin films on mica and glass surfaces depending on deposition conditions.
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