Synthesis and characterization of tetraphenyl-21,23-dideazaporphyrin: the best evidence yet that porphyrins really are the [18]annulenes of nature.
McMurry coupling of a pyrrole bisacrylaldehyde afforded a dipyrrolic macrocycle that is structurally midway between 1,10-diaza[18]annulene and the porphyrins. The diprotonated dication of this system retains porphyrin-like properties and provides insights into the nature of porphyrinoid aromaticity.
Lash
Timothy D
TD
Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, USA. tdlash@ilstu.edu
Jones
Sarah A
SA
Ferrence
Gregory M
GM
D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D011166:Porphyrins; C554671:tetraphenyl-21,23-dideazaporphyrin