Intermolecular hydrogen-bonded organic semiconductors—Quinacridone versus pentacene

Quinacridone is a five-ring hydrogen-bonded molecule analogous in structure and size to the well-known organic semiconductor pentacene. Unlike pentacene, quinacridone has limited intramolecular π-conjugation and becomes highly colored in the solid state due to strong intermolecular electronic coupling. We found that quinacridone shows a field-effect mobility of 0.1 cm2/V·s, comparable to mobilities of pentacene in similarly prepared devices. Photoinduced charge generation in single-layer quinacridone metal-insulator-metal diodes is more than a hundred times more efficient than in pentacene devices. Photoinduced charge transfer from quinacridone to C60 is not effective, as evidenced by measurements in heterojunctions with C60. Hydrogen-bonded organic solids may provide new avenues for organic semiconductor design.

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