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Washington University Undergraduate Research Digest: WUURD 7(1)
Peer Editors: Ashley Brosius and Rebecca Tsevat; Peer Editor: Sophia Hayes
Photoreactive compounds have many potential applications including novel sunscreens, polarization filters and optical switches in advanced molecular computing methods. This study focuses on [2+2] photocyclo- addition reactions in two compounds: a supramolecular complex and a cinnamoyl-substituted polymer. Nuclear magnetic resonance spectroscopy (NMR) is used to monitor these reactions in the solid state. The kinetics curve for the supramolecular complex photoreaction has been determined under wavelength selective irradiation. This study attempts to resolve several issues with previous analyses of the polymer photoreaction: limited photoreaction even after long irradiation times, and signal resolution issues when observing the photoreaction in the polymer. UV-Visible spectroscopy provides insight into the issue of limited photoreaction, and suggests that previous studies may have irradiated the polymer at photon energies that are too low. Future irradiations should focus on a range at higher photo energies, further into the UV region. Finally, the NMR signal resolution issues will be circumvented by isotopically labeling the polymer at the site of photoreaction. In this study, a precursor to the labeled cinnamoyl- substituted polymer, 13C-labeled cinnamic acid, has been produced, and its identity is characterized by liquids NMR (both 1H and 13C).
From the Washington University Undergraduate Research Digest: WUURD, Volume 7, Issue 1, Fall 2011. Published by the Office of Undergraduate Research, Joy Zalis Kiefer Director of Undergraduate Research and Assistant Dean in the College of Arts & Sciences; Kristin Sobotka, Editor.
Hirsh, David A., "Characterization os [2+2] Photocycloaddition Reactions in the Solid State Using NMR" (2011). Washington University Undergraduate Research Digest, Volume 7, Issue 1.