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|Title:||Synthesis of a π-extended azacorannulenophane enabled by strain-induced 1,3-dipolar cycloaddition||Authors:||Zhang, Xinjiang
Mackinnon, Marc R.
Bodwell, Graham J.
|Keywords:||Science::Chemistry||Issue Date:||2022||Source:||Zhang, X., Mackinnon, M. R., Bodwell, G. J. & Ito, S. (2022). Synthesis of a π-extended azacorannulenophane enabled by strain-induced 1,3-dipolar cycloaddition. Angewandte Chemie International Edition, 61(16), e202116585-. https://dx.doi.org/10.1002/anie.202116585||Journal:||Angewandte Chemie International Edition||Abstract:||The first example of a cyclophane bearing a nitrogen-containing buckybowl was synthesized via sequential 1,3-dipolar cycloaddition and palladium-catalyzed intramolecular cyclization. The key to the successful synthesis is the strain-induced 1,3-dipolar cycloaddition of a polycyclic aromatic azomethine ylide to the K-region of (2,7)pyrenophane. The resulting π-extended azacorannulenophane exhibits intriguing structural and physical properties, including unique variation of bowl depth, extraordinarily high-field chemical shifts in its 1 H NMR spectrum, a decreased HOMO-LUMO gap, and a red shift in the absorption/emission spectrum, when compared to those of the parent azacorannulene. These characteristics are derived from both the π-extension to the polycyclic aromatic system in the cyclophane structure and the increased curvature enforced by the seven-carbon aliphatic chain.||URI:||https://hdl.handle.net/10356/161664||ISSN:||1433-7851||DOI:||10.1002/anie.202116585||Schools:||School of Physical and Mathematical Sciences||Rights:||This is the peer reviewed version of the following article: Zhang, X., Mackinnon, M. R., Bodwell, G. J. & Ito, S. (2022). Synthesis of a π-extended azacorannulenophane enabled by strain-induced 1,3-dipolar cycloaddition. Angewandte Chemie International Edition, 61(16), e202116585-, which has been published in final form at https://doi.org/10.1002/anie.202116585. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.||Fulltext Permission:||open||Fulltext Availability:||With Fulltext|
|Appears in Collections:||SPMS Journal Articles|
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