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

Abstract

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 (Φ 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. H 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.

Phenyl-Linked Anthracene-Based Macrocycles with Geometrically Tunable Optical Properties

“…26,27 A macrocyclic diphenylanthracene dimer was successfully synthesized by Iyoda et al using the electron-transfer oxidation of Lipshutz cuprate in 2018 ( Figure 1). 42 Although these achievements made progress, the synthesis of smaller macrocycles with anthracene units still remains a challenge, such as a phenyl-linked 1,8-anthracene dimer, due to the high strain at the 1,8-position and the rigid π-frame of anthracene.…”