Benzynes produced by the thermal cycloisomerization of tetrayne substrates [i.e., by the hexadehydro-Diels-Alder (HDDA) reaction] react with perylenes to produce novel naphthoperylene derivatives. Cyclic voltammetry and absorption and emission properties of these compounds are described. DFT studies shed additional light on the dearomatization that accompanies the reaction as well as some of the spectroscopic behavior.
Bibliographical noteFunding Information:
This investigation was supported by a grant awarded by the U.S. Department of Health and Human Services (National Institute of General Medical Sciences, GM65597, and the National Cancer Institute, CA76497). Portions of this work were performed with hardware and software resources available through the University of Minnesota Supercomputing Institute (MSI). Some of the NMR data were recorded using instrumentation purchased with funds awarded through the NIH Shared Instrumentation Grant Program (S10OD011952).
© 2016 American Chemical Society.