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Squarephaneic tetraanhydride: a conjugated square‐shaped cyclophane for the synthesis of porous organic materials
OA Location
Author(s)
Eder, Simon
Ding, Bowen
Thornton, Daisy B
Sammut, Darlene
White, Andrew JP
Type
Journal Article
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.
Date Issued
2022-11-25
Date Acceptance
2022-09-30
Citation
Angewandte Chemie, 2022, 134 (48), pp.1-8
URI
URL
DOI
ISSN
0044-8249
Publisher
Wiley
Start Page
1
End Page
8
Journal / Book Title
Angewandte Chemie
Volume
134
Issue
48
Replaces
10044/1/100353
Copyright Statement
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
License URL
Sponsor
FWF Austrian Science Fund (FWF)
Commission of the European Communities
EPRSC
Engineering & Physical Science Research Council (EPSRC)
Engineering & Physical Science Research Council (EPSRC)
Identifier
https://www.ncbi.nlm.nih.gov/pubmed/38504923
PII: ANGE202212623
Grant Number
J 4463
796024
EP/V048686/1
EP/V048686/1
EP/T031425/1
Subjects
Aromaticity
Carboxylic Anhydrides
Conjugated Macrocycles
Imides
Organic Materials
Publication Status
Published
Coverage Spatial
Germany
Article Number
e202212623
Date Publish Online
2022-09-30