TY - JOUR
T1 - 2,6-Diacylnaphthalene-1,8:4,5-bis(dicarboximides)
T2 - Synthesis, reduction potentials, and core extension
AU - Polander, Lauren E.
AU - Pandey, Laxman
AU - Romanov, Alexander
AU - Fonari, Alexandr
AU - Barlow, Stephen
AU - Seifried, Brian M.
AU - Timofeeva, Tatiana V.
AU - Brédas, Jean Luc
AU - Marder, Seth R.
PY - 2012/7/6
Y1 - 2012/7/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84863630927&partnerID=8YFLogxK
U2 - 10.1021/jo3006232
DO - 10.1021/jo3006232
M3 - Article
C2 - 22621328
AN - SCOPUS:84863630927
SN - 0022-3263
VL - 77
SP - 5544
EP - 5551
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 13
ER -