A new carboxy-Zn(II) phthalocyanine bearing rigid 2,6-diarylphenyl peripheral substituents linked to the macrocycle through alkynyl spacers has been prepared by a convergent approach, which implies a triple Sonogashira coupling between the formyltriiodoZnPc and the corresponding terminal alkyne. Indeed, the introduction of this type of pi-conjugated peripheral substituents accounts for a remarkable red shift of the phthalocyanine Q-band until ca. 700 nm. However, aggregation phenomena could not be supressed and may explain the moderate overall efficiencies achieved with these devices.
Felix Thomas Eickemeyer, Jovana Milic
Jérôme Waser, Stephanie Grace Elizabeth Amos