Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials**

Simon Eder, Bowen Ding, Daisy B. Thornton, Darlene Sammut, Andrew J.P. White, Felix Plasser, Ifan E.L. Stephens, Martin Heeney, Stefano Mezzavilla, Florian Glöcklhofer

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Aromatic carboxylic anhydrides are ubiquitous building blocks in organic materials chemistry and have received considerable attention in the synthesis of organic semiconductors, pigments, and battery electrode materials. Here we extend the family of aromatic carboxylic anhydrides with a unique new member, a conjugated cyclophane with four anhydride groups. The cyclophane is obtained in a three-step synthesis and can be functionalised efficiently, as shown by the conversion into tetraimides and an octacarboxylate. Crystal structures reveal the high degree of porosity achievable with the new building block. Excellent electrochemical properties and reversible reduction to the tetraanions are shown for the imides; NMR and EPR measurements confirm the global aromaticity of the dianions and evidence the global Baird aromaticity of the tetraanions. Considering the short synthesis and unique properties, we expect widespread use of the new building block in the development of organic materials.
Original languageEnglish (US)
JournalAngewandte Chemie - International Edition
Volume61
Issue number48
DOIs
StatePublished - Nov 25 2022
Externally publishedYes

ASJC Scopus subject areas

  • General Chemistry
  • Catalysis

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