Core Perylene Diimide Designs via Direct Bay- and ortho-(Poly)trifluoromethylation: Synthesis, Isolation, X-ray Structures, Optical and Electronic Properties

Tyler T. Clikeman, Eric V. Bukovsky, Xue Bin Wang, Yu Sheng Chen, Garry Rumbles, Steven H. Strauss, Olga V. Boltalina

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

We developed an efficient solvent- and catalyst-free direct polytrifluoromethylation of solid perylene-3,4,9,10-tetracarboxylic dianhydride that produced a new family of (poly)perfluoroalkyl bay- and ortho-substituted PDIs with two different imide substituents. Direct hydrogen substitution with CN group led to the synthesis of a cyanated perfluoroalkyl PDI derivative for the first time. Absorption, steady-state and time-resolved emission, X-ray diffraction, electrochemical, and gas-phase electron affinity data allowed for systematic studies of substitution effects at bay, ortho, and imide positions in the new PDIs. Solid-state packing showed remarkable variations in the intermolecular interactions that are important for charge transport and photophysical properties. Analysis of the electrochemical data for 143 electron poor PDIs, including newly reported compounds, revealed some general trends and peculiar effects from substituting electron-withdrawing groups at all three positions.

Original languageEnglish
Pages (from-to)6641-6654
Number of pages14
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number30
DOIs
Publication statusPublished - Oct 1 2015

Keywords

  • Aromatic substitution
  • Dyes/pigments
  • Electrochemistry
  • Fluorescence
  • Fluorine
  • Liquid chromatography

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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