Degradation of organic semiconductors in the presence of oxygen is one of the bottlenecks preventing their wide-spread use in optoelectronic devices. The first step towards such degradation in functionalized pentacene (Pn) derivatives is formation of endoperoxide (EPO), which can either revert back to the parent molecule or proceed to molecule decomposition. We present the study of reversibility of EPO formation through probing the photophysical properties of functionalized fluorinated pentacene (Pn-R-F8) derivatives. Experiments are done in solutions and in films both at the single molecule level and in the bulk. In solutions, degradation of optical absorption and its partial recovery after thermolysis were quantified for various derivatives depending on the solvent. At the single molecule level, low concentrations of each type of molecules were imaged in a variety of polymer matrices at 633 nm excitation at room temperature in air using wide-field fluorescence microscopy. Fluorescence time trajectories were collected and statistically analyzed to quantify blinking due to reversible EPO formation depending on the host matrix. To understand the physical changes of the molecular system, a Monte Carlo method was used to create a multi-level simulation, which enabled us to relate the change in the molecular transition rates to the experimentally measured parameters. At the bulk level, photoluminescence decay due to photobleaching and recovery due to EPO reconversion were measured for the same derivatives incorporated into various matrices. These studies provide insight into the synergistic effect of the local nanoenvironment and molecular side groups on the oxygen-related degradation and subsequent recovery which is important for development of organic electronic devices.

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Published in Proceedings of SPIE, v. 10529, Organic Photonic Materials and Devices XX, article 105290Z, p. 1-9.

© 2018 SPIE. One print or electronic copy may be made for personal use only. Systematic reproduction and distribution, duplication of any material in this publication for a fee or for commercial purposes, and modification of the contents of the publication are prohibited.

Nicole Quist, Mark Li, Ryan Tollefsen, Michael Haley, John Anthony, and Oksana Ostroverkhova, "Effect of molecular side groups and local nanoenvironment on photodegradation and its reversibility," Proc. SPIE 10529, Organic Photonic Materials and Devices XX, 105290Z (February 21, 2018). DOI: https://doi.org/10.1117/12.2291065

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The National Science Foundation (DMR-1207309) and Oregon State University (OSU) URISC program (M. Li) are acknowledged for financial support.