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Azatriseptanes: Strained Framework Analogs of [7,7,7]Circulenes


Zhang, Kai; Hope, Philip A; El Bitar Nehme, Mélissa; Linden, Anthony; Spingler, Bernhard; Rickhaus, Michel (2023). Azatriseptanes: Strained Framework Analogs of [7,7,7]Circulenes. Chemistry, 29(14):e202203954.

Abstract

The syntheses and characterizations of heptagon-embedded polycyclic aromatic compounds are essential for understanding the effect of negative curvature on carbon allotropes such as fullerene and graphene that have applications in functional organic materials. However, owing to the synthetic difficulties in functionalizing and embedding 7-membered rings, these strain-challenged structures are relatively unexplored. We report here the synthesis and photophysical characterization of a triarylamine core bridged with ethane chains at the 2,2’-positions. In doing so, we provide access to the first heterocycle containing three fused heptagon rings with a nitrogen at its core (BATA-NHAc). DFT calculations and X-ray crystallography reveal a remarkably strained structure wherein two of the bridged aryl units approach coplanarity, whilst the third ring is twisted out of plane. The unique conformation of BATA-NHAc results in distinctive photophysical and electrochemical properties that open new avenues in understanding the structure-property relationships of curved π-aromatics and the construction of π-frameworks of increasing complexion.

Abstract

The syntheses and characterizations of heptagon-embedded polycyclic aromatic compounds are essential for understanding the effect of negative curvature on carbon allotropes such as fullerene and graphene that have applications in functional organic materials. However, owing to the synthetic difficulties in functionalizing and embedding 7-membered rings, these strain-challenged structures are relatively unexplored. We report here the synthesis and photophysical characterization of a triarylamine core bridged with ethane chains at the 2,2’-positions. In doing so, we provide access to the first heterocycle containing three fused heptagon rings with a nitrogen at its core (BATA-NHAc). DFT calculations and X-ray crystallography reveal a remarkably strained structure wherein two of the bridged aryl units approach coplanarity, whilst the third ring is twisted out of plane. The unique conformation of BATA-NHAc results in distinctive photophysical and electrochemical properties that open new avenues in understanding the structure-property relationships of curved π-aromatics and the construction of π-frameworks of increasing complexion.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:General Chemistry, Catalysis, Organic Chemistry
Language:English
Date:7 March 2023
Deposited On:09 Jan 2023 08:59
Last Modified:29 Mar 2024 02:37
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0947-6539
Additional Information:This is the peer reviewed version of the following article: Chem. Eur. J. 2022, e202203954, which has been published in final form at https://doi.org/10.1002/chem.202203954. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving (http://olabout.wiley.com/WileyCDA/Section/id-820227.html#terms).
OA Status:Green
Publisher DOI:https://doi.org/10.1002/chem.202203954
Project Information:
  • : FunderSwiss National Science Foundation
  • : Grant IDPZ00P2_180101
  • : Project Title
  • Content: Accepted Version
  • Language: English