Borylated Subphthalocyanines: Versatile Precursors for the Preparation of Functional Bowl-Shaped Aromatics

The peripheral borylation of porphyrinoids has become a key step to prepare advanced functional materials. This study reports the synthesis, electronic properties, and reactivity of borylated subphthalocyanines. These compounds, which are prepared by Suzuki-Miyaura borylation in excellent yields, are easily purified, display a great stability, and serve as powerful starting materials for the post-functionalization of SubPcs via cross-coupling reactions. Remarkably, this novel approach is more efficient than the methodologies already described and enables the preparation of exotic systems, such as SubPc dimeric species linked by C-C bonds, which are not accessible so far and present promising properties for optoelectronic devices.