Core-modified rubyrins with phenanthrene-fused pyrrole rings: Highly selective and tunable response to Hg2+ ions

Three fused-ring-expanded rubyrins with modified macrocyclic core have been synthesized and characterized. A series of spectroscopic, electrochemical measurements and a set of theoretical calculations demonstrate that the core-modification of the inner core of rubyrins has a large influence on the electronic structure. Colorimetric changes are observe that demonstrate that these core-modified rubyrins could be used as selective Hg2+ ion sensors. These properties can be fine-tuned by introducing lipophilic substituents on the meso-aryl rings.