A. Maliakal, K. Raghavachari, H. Katz
Nov 6, 2004
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Journal
Chemistry of Materials
Abstract
The organic semiconductor pentacene (1) has shown the highest field effect mobilities in thin films of any organic semiconductor, yet suffers from instability toward oxidation. 6,13-Bis(triisopropylsilylethynyl)pentacene (2) has been reported as an interesting functionalized pentacene which is soluble in common organic solvents and exhibits high carrier mobility (>0.1 cm2/Vs) in thin film transistor devices. In our investigations of 2, we were surprised by its remarkable stability in solution. Using UV−vis spectroscopy we observe that under ambient light conditions, 2 is approximately 50× more stable toward degradation in air-saturated tetrahydrofuran solution as compared to unsubstituted pentacene. Previous investigators have implicated oxygen in the mechanism of photodegradation of pentacene. In this study, quantum chemical calculations have been performed which demonstrate that alkynyl functionalization at the 6 and 13 positions reduces the rate of photooxidation in two ways. First, alkynyl substitutio...