title: Design and synthesis of porphyrins bearing rigid hydrogen bonding motifs: highly versatile building blocks for self-assembly of polymers and discrete arrays.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, Hunter College of the City University of New York, 695 Park Avenue, New York, New York 10021, USA.
authors.forename: X
authors.initials: X
authors.lastname: Shi
authors.forename: K M
authors.initials: KM
authors.lastname: Barkigia
authors.forename: J
authors.initials: J
authors.lastname: Fajer
authors.forename: C M
authors.initials: CM
authors.lastname: Drain
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D015195:Drug Design; D006860:Hydrogen Bonding; D008652:Mesoporphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000447:Aldehydes; D008652:Mesoporphyrins; D011108:Polymers