242-51-3Relevant articles and documents
Oxygen- and sulfur-bridged bianthracene V-shaped organic semiconductors
Mitsui, Chikahiko,Yamagishi, Masakazu,Shikata, Ryoji,Ishii, Hiroyuki,Matsushita, Takeshi,Nakahara, Katsumasa,Yano, Masafumi,Sato, Hiroyasu,Yamano, Akihito,Takeya, Jun,Okamoto, Toshihiro
, p. 931 - 938 (2017)
Highly π-electron conjugated backbones are of great interest for applications to organic electronic devices, e.g., organic field-effect transistors and organic photovoltaics. A series of oxygen- and sulfur-bridged bianthracene V-shaped π-electronic cores are facilely synthesized. Both V-shaped molecules possess bent structures induced by the intermolecular interaction in a herringbone-packing manner. A theoretical calculation study reveals that the driving force of the bent structures originates from the strong dispersion energy. Also, the bent conformation plays a vital role in the formation of a dense packing structure, resulting in an attractive intermolecular overlap. An examination of the charge transport demonstrates that the hole mobility is up to 2.0 sq cm/Vs. Sulfur-bridged V-shaped π-electronic cores are more suitable for two-dimensional carrier-transport than oxygen-bridged analogs.
Aromatic Metamorphosis of Dibenzofurans into Triphenylenes Starting with Nickel-Catalyzed Ring-Opening C-O Arylation
Kurata, Yuto,Otsuka, Shinya,Fukui, Norihito,Nogi, Keisuke,Yorimitsu, Hideki,Osuka, Atsuhiro
supporting information, p. 1274 - 1277 (2017/03/22)
A new class of aromatic metamorphosis has been developed in which dibenzofurans were converted into triphenylenes. This transformation is composed of three successive operations: (1) nickel-catalyzed ring-opening C-O bond arylation with arylmagnesium bromides, (2) trifluoromethanesulfonylation (triflation) of the resulting hydroxy moiety with Tf2O, and (3) palladium-catalyzed or photoinduced ring closure. In the last ring-closing step, the photoinduced process has proven to be more productive than the palladium-catalyzed one. By employing π-extended dinaphthofuran as the substrate, dorsally benzo-fused [5]helicene was obtained in a satisfactory yield.