Multi-fold Sonogashira coupling: a new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties

Abstract

For the first time, a direct single-step one-pot route to access nine new symmetric tetraalkynylated anthracenes via Pd(CH₃CN)₂Cl₂/cataCXium®A catalyzed tetra-fold Sonogashira coupling is reported. Five of these tetraalkynylated anthracenes have been crystallographically characterized, with two of them exhibiting multiple interactions that significantly shorten the inter-planar distances in the solid-state structure. The rich photophysical properties exhibited by these molecules hold immense promise for future applications in sensors and optoelectronic devices. Two of the considered tetraalkynylated anthracenes comprising a D–π-A–π-D motif demonstrate solvatochromism and halochromism, with one of them showing a low bandgap of 1.79 eV. The remaining compounds demonstrate bandgaps in the range of 1.79–2.04 eV.