title: Post-synthetic modification of hangman porphyrins synthesized on the gram scale.
abstract: We report a multi-gram scale synthesis of methyl 6-formyl-4-dibenzofurancarboxylate and its subsequent use in the gram scale synthesis of a dibenzofuran-functionalized hangman porphyrin containing a pendant carboxylic acid (HPD-CO2H). HPD-CO2H can be isolated as a free carboxylic acid in high purity with minimal purification. Post-synthetic modification of HPD-CO2H allows for the introduction of any desired pendant group in good yields, resulting in a practical amount of hangman porphyrin ligand with an easily customizable second coordination sphere. The cobalt complexes of these hangman porphyrins are shown to be active proton reduction electrocatalysts.
authors: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St, Cambridge, MA 02138 (USA).
authors: Daniel J
authors: DJ
authors: Graham
authors: Shao-Liang
authors: SL
authors: Zheng
authors: Daniel G
authors: DG
authors: Nocera
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D003035:Cobalt / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D011166:Porphyrins; D003035:Cobalt
keywords: electrocatalysis; gram scale; hangman porphyrin; hydrogen; porphyrin