Acenes are organic semiconductor compounds that show great promise in organic field effect transistor (OFET) and organic light emitting diode (OLED) applications.
While large acenes like heptacene are predicted to have attractive electronic properties, they rapidly oxidize under ambient conditions, a serious limitation that becomes increasingly problematic with increasing acene length.
In order to utilize large acenes as semiconducting nanoelements in the low cost, high-rate manufacture of electronic devices including OFETs and OLEDs, they must first be made resistant to oxidation. Using newly discovered substituent effects as a guide, we have now demonstrated the formation of an unusually persistent heptacene derivative that can be explored as a semiconducting nanoelement in OFET and OLED applications.
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Image: (Top) Normalized absorbances for four heptacene derivatives as a function of time exposed to light and air (1x10-4 M initial conc.) at 25 oC. (Bottom) Normalized UV-vis (blue line) and fluorescence (green line) spectra of the heptacene derivative that shows unusual resistance to oxidation. The long wavelength absorptions in the UV-vis spectrum indicate a small bandgap semiconductor while the fluorescence spectrum indicates green light emission. Reproduced with permission from Kaur I, et al. J. Am. Chem. Soc. 2009;131(10):3424-3425. Copyright 2009 American Chemical Society.