The major challenge in organic electronics concerns the stability of organic semiconductor materials which affects the operational lifetime of devices. Recent reports have shown that hydrogen-bonded pigments of the indigoid family are air-and moisture resistant. The magenta pigment quinacridone, a hydrogen-bonded molecule in the solid state with a pentacene like frame, is a perfect example for extraordinary chemical stability. Here, studies using in situ spectroscopic methods comparing quinacridone and pentacene are presented. A different spectral response of their radical cations is observed upon chemical doping. While in pentacene the barrier between doping and irreversible overoxidation is small, this stability toward overoxidation is increased by the heteroatomic structure, leading to hydrogen-bonded quinacridone. This work provides insight into molecular design principles that may lead to next-generation organic semiconductors with enhanced stability and performance.