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10-Mesityl-1,8-diphenylanthracene Dimer: Synthesis, Structure, and Properties

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posted on 02.03.2018, 00:00 by Atsumi Shirai, Hiroto Sano, Yuki Nakamura, Masataka Takashika, Hiroyuki Otani, Masashi Hasegawa, Shin-ichiro Kato, Masahiko Iyoda
Macrocyclic 10-mesityl-1,8-diphenylanthracene dimer 4 was synthesized by using the electron-transfer oxidation of Lipshutz cuprate derived from 1,8-bis­(4-bromophenyl)-10-mesityl-anthracene 7 in moderate yield. This dimer 4 is a considerably fluorescent molecule (ΦF 0.40) with high thermal, photo, and air stability. The X-ray analysis of 4 revealed a unique structure with a small inner cavity which can incorporate a small molecule or atom. 1H NMR spectra in solution and emission spectra of 4 in the solid state showed that copper­(I) ion was incorporated to form a 1:1 complex 4·CuOTf, whereas silver­(I) ion only weakly interacted with 4 under similar conditions.