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Updated: May 22, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
2,6-Diacylnaphthalene-1,8:4,5-bis(dicarboximides): synthesis, reduction potentials, and core extension
Lauren E Polander1, Laxman Pandey, Alexander Romanov
1School of Chemistry and Biochemistry, Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, USA.
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.
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