4.3 Article

Perfluoroalkylated anthracene endoperoxide: Synthesis, characterization, crystal structure analysis, and computational insights

Journal

JOURNAL OF FLUORINE CHEMISTRY
Volume 235, Issue -, Pages -

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2020.109548

Keywords

Endoperoxide; Anthracene; Fluorine; Perfluoroalkylation; X-ray crystallography; Crystal structure

Funding

  1. NSF [ACI-1626516, CHE1355677]
  2. U.S. Army Research Office [W911NF-09-10472]
  3. South Dakota Governor's Office of Economic Development through the Center for Fluorinated Functional Materials
  4. NSFMRI [CHE-1229035, CHE-1919637]

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Aromatic endoperoxides serve as important intermediate species toward generating singlet state oxygen, which is key to photodynamic therapy applications. Gaining insights for fine-tuning endoperoxide stability and degree of oxygen-oxygen bond activation is of fundamental and practical interest for the chemical and medicinal communities. We report here that 9,10-bisperfluorooctyl-anthracene, upon exposing to light and air, is almost quantitatively converted to 9,10-bisperfluorooctyl-anthracene endoperoxide (compound 1) at room temperature. H-1 NMR spectra and the X-ray crystal structure revealed that the resulting compound 1 is stable at room temperature without further decomposition. The crystal structure analysis showed that the compound 1 is stabilized by F center dot center dot center dot O intramolecular interactions along with F center dot center dot center dot F, F center dot center dot center dot H and F center dot center dot center dot C intermolecular interactions. DFT calculations further indicate that the degree of oxygen-oxygen bond activation in anthracene endoperoxides, reflected as changes of O-O, C-O bond distances, may not solely depend on the electronic effect of substituents at the 9,10- positions. This uncertainty warrants further investigation both experimentally and computationally.

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