Development of novel symmetrical and asymmetrical alkyne-functionalized silicon phthalocyanines, a potential functionality control for organic semiconductors

Metal phthalocyanines offer a wide variety of chemical modifications that can be exploited to tailor the material properties to target different applications. This work demonstrates the electrochemical and optical fine-tuning of silicon phthalocyanine (SiPc) derivatives by introducing axial asymmetry. When integrated into organic thin-film transistors (OTFTs) as organic semiconductors, the studied asymmetric derivatives exhibit modest [Formula: see text]-type performance relative to symmetrical analogs. The highest-performing derivative, an asymmetrical fluorinated SiPc, also demonstrated ambipolarity, with performance similar to its fluorinated symmetrical counterpart. Owing to the presence of terminal alkynes on the axial handles, further chemical modifications were performed via click chemistry to demonstrate the possibility of chemical tuning post-SiPc synthesis. The success of the click reaction suggests that these derivatives can be applied in the future, for example, to attach them to polymers, to surface-graft OTFTs, and other applications.