Iptycene-derived pyridazines and phthalazines.

TitleIptycene-derived pyridazines and phthalazines.
Publication TypeJournal Article
Year of Publication2007
AuthorsBouffard, J, Eaton, RF, M\üller, P, Swager, TM
JournalThe Journal of organic chemistry
Date Publisheddec
Keywordsiptycene deriv pyridazine phthalazine prepn, phthalazine benzenonaphthophthalazine dimer trimer prepn

The synthesis of new heterocyclic oligo(phenylene) analogues based on soluble, nonaggregating 1,2-diazines is reported. Improved palladium-catalyzed reductive coupling methods were developed to allow for the preparation of large quantities of iptycene-derived bipyridazines and biphthalazines, and the controlled synthesis of well-defined oligomers up to sexipyridazine. Crystallographic, spectroscopic, and computational evidence indicate that in these analogues, hindrance at the ortho position is relaxed relative to poly(phenylenes). The resulting building blocks are promising for incorporation in conjugated electronics materials, and as new iptycene-derived ligands for transition metals.