Reactions of HDDA-Derived Benzynes with Perylenes: Rapid Construction of Polycyclic Aromatic Compounds

Feng Xu, Xiao Xiao, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)5636-5639
Number of pages4
JournalOrganic Letters
Volume18
Issue number21
DOIs
StatePublished - Nov 4 2016

Bibliographical note

Funding 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).

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