Design and synthesis of porphyrins bearing rigid hydrogen bonding motifs: highly versatile building blocks for self-assembly of polymers and discrete arrays.
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.
Shi
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Department of Chemistry and Biochemistry, Hunter College of the City University of New York, 695 Park Avenue, New York, New York 10021, USA.
Barkigia
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Fajer
J
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Drain
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CM
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
D000447:Aldehydes; D008652:Mesoporphyrins; D011108:Polymers