Iptycene-Derived pyridazines and phthalazines

Jean Bouffard, Robert F. Eaton, Peter Müller, Timothy M. Swager

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)10166-10180
Number of pages15
JournalJournal of Organic Chemistry
Volume72
Issue number26
DOIs
StatePublished - 21 Dec 2007

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