Corannulene-Based Electron Acceptors: Combining Modular and Practical Synthesis with Electron Affinity and Solubility

Viktor Barát, Maja Budanovic, Si Man Tam, June Huh, Richard D. Webster, Mihaiela C. Stuparu

Research output: Contribution to journalArticle

Abstract

It is shown in this work that high electron affinity can be combined with high solubility and practical accessibility in corannulene-based electron acceptors. The electron affinity originates from the presence of three different types of electron-withdrawing groups (imide, sulfone, and trifluoromethyl) on the aromatic scaffold. The imide substituent further hosts a long alkyl chain (C18H37) to boast solubility in a wide range of organic solvents. The synthesis is modular and consists of three simple steps from a commonly available corannulene derivative with an overall isolated yield of 22–27 %.

Original languageEnglish
Pages (from-to)3231-3235
Number of pages5
JournalChemistry - A European Journal
Volume26
Issue number15
DOIs
Publication statusPublished - 2020 Mar 12

Keywords

  • corannulene
  • electron-deficient compounds
  • fused-ring systems
  • polycyclic aromatic hydrocarbons
  • sulfones

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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