Oxidation of 2,9-Diphenyl-1,10-phenanthroline to Generate the 5,6-Dione and Its Subsequent Alkylation Product

One group of ligands used in transition metal complexes is synthesized by derivatizing 1,10‐phenanthroline. These metal complexes are of interest for study in the field of photovoltaic devices and solar fuels. Previous strategies for obtaining the 5,6‐diones of substituted 1,10‐phenanthrolines do no...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2014-09, Vol.51 (5), p.1468-1471
Main Authors: Lehnig, Ammon P., Lazorski, Megan S., Mingroni, Michael, Pacheco, Kimberly A. O., Michael Elliott, C.
Format: Article
Language:English
Subjects:
Oxidation
Solar energy
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Summary:One group of ligands used in transition metal complexes is synthesized by derivatizing 1,10‐phenanthroline. These metal complexes are of interest for study in the field of photovoltaic devices and solar fuels. Previous strategies for obtaining the 5,6‐diones of substituted 1,10‐phenanthrolines do not work for 2,9‐diphenyl‐1,10‐phenanthroline due to undesired products resulting from oxidation of the phenyl substituents. However, 2,9‐diphenyl‐1,10‐phenanthroline‐5,6‐dione can be obtained in reasonable yield by oxidation with BrO3− in weak aqueous acid. The resulting dione can be converted directly to the 5,6‐dialkoxy product upon two electron reduction in aprotic solvent followed by treatment with appropriate alkylating agents.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.2105