Journal article
The anti-aromatic dianion and aromatic tetraanion of [18]annulene
- Abstract:
- π-Conjugated macrocycles behave differently from analogous linear chains because their electronic wavefunctions resemble a quantum particle on a ring, leading to aromaticity or anti-aromaticity. [18]Annulene, (CH)18, is the archetypal non-benzenoid aromatic hydrocarbon. Molecules with circuits of 4n + 2 π electrons, such as [18]annulene (n = 4), are aromatic, with enhanced stability and diatropic ring currents (magnetic shielding inside the ring), whereas those with 4n π electrons, such as the dianion of [18]annulene, are expected to be anti-aromatic and exhibit the opposite behaviour. Here we use 1H NMR spectroscopy to re-evaluate the structure of the [18]annulene dianion. We also show that it can be reduced further to an aromatic tetraanion, which has the same shape as the dianion. The crystal structure of the tetraanion lithium salt confirms its geometry and reveals a metallocene-like sandwich, with five Li+ cations intercalated between two [18]annulene tetraanions. We also report a heteroleptic sandwich, with [18]annulene and corannulene tetraanion decks.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 4.2MB, Terms of use)
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- Publisher copy:
- 10.1038/s41557-024-01469-1
Authors
- Publisher:
- Springer Nature
- Journal:
- Nature Chemistry More from this journal
- Volume:
- 16
- Issue:
- 6
- Pages:
- 998–1002
- Place of publication:
- England
- Publication date:
- 2024-03-06
- Acceptance date:
- 2024-02-02
- DOI:
- EISSN:
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1755-4349
- ISSN:
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1755-4330
- Pmid:
-
38448656
- Language:
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English
- Keywords:
- Pubs id:
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1776549
- Local pid:
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pubs:1776549
- Deposit date:
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2024-06-05
- ARK identifier:
Terms of use
- Copyright holder:
- Stawski et al.
- Copyright date:
- 2024
- Rights statement:
- © The Author(s) 2024. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons. org/licenses/by/4.0/.
- Licence:
- CC Attribution (CC BY)
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