2,6-Diacylnaphthalene-1,8:4,5-bis(dicarboximides): Synthesis, reduction potentials, and core extension

Lauren E. Polander, Laxman Pandey, Alexander Romanov, Alexandr Fonari, Stephen Barlow, Brian M. Seifried, Tatiana V. Timofeeva, Jean-Luc Bredas, Seth R. Marder*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

2,6-Diacyl derivatives of naphthalene-1,8:4,5-bis(dicarboximide)s have been synthesized via Stille coupling reactions of the corresponding 2,6-distannyl derivative with acyl halides. Reaction of these diketones with hydrazine gave phthalazino[6,7,8,1-lmna]pyridazino[5,4,3-gh][3,8]phenanthroline-5,11(4H,10H) -dione fused-ring derivatives. The products were characterized by UV-vis absorption spectroscopy and electrochemistry, modeled using density functional theory calculations, and, in some cases, studied and compared using single-crystal X-ray diffraction.

Original languageEnglish (US)
Pages (from-to)5544-5551
Number of pages8
JournalJournal of Organic Chemistry
Volume77
Issue number13
DOIs
StatePublished - Jul 6 2012

ASJC Scopus subject areas

  • Organic Chemistry

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