title: 2,6-Diacylnaphthalene-1,8:4,5-bis(dicarboximides): synthesis, reduction potentials, and core extension.
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.
authors.affiliation: School of Chemistry and Biochemistry, Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, USA.
authors.forename: Lauren E
authors.initials: LE
authors.lastname: Polander
authors.forename: Laxman
authors.initials: L
authors.lastname: Pandey
authors.forename: Alexander
authors.initials: A
authors.lastname: Romanov
authors.forename: Alexandr
authors.initials: A
authors.lastname: Fonari
authors.forename: Stephen
authors.initials: S
authors.lastname: Barlow
authors.forename: Brian M
authors.initials: BM
authors.lastname: Seifried
authors.forename: Tatiana V
authors.initials: TV
authors.lastname: Timofeeva
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Brédas
authors.forename: Seth R
authors.initials: SR
authors.lastname: Marder
mesh_terms: D018360:Crystallography, X-Ray; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007094:Imides / Q000737:chemistry*; D008958:Models, Molecular; D009281:Naphthalenes / Q000737:chemistry*; D009947:Organotin Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D011789:Quantum Theory
chemical_list: D006846:Hydrocarbons, Halogenated; D007094:Imides; D009281:Naphthalenes; D009947:Organotin Compounds