Template‐Directed Synthesis of Strained meso‐meso‐Linked Porphyrin Nanorings

Van Raden, Jeff M.; Deng, Jie‐Ren; Gotfredsen, Henrik; Hergenhahn, Janko; Clarke, Michael; Edmondson, Matthew; Hart, Jack; O'Shea, James N.; Duarte, Fernanda; Saywell, Alex; Anderson, Harry L.

Abstract

Strained macrocycles display interesting properties, such as conformational rigidity, often resulting in enhanced π-conjugation or enhanced affinity for non-covalent guest binding, yet they can be difficult to synthesize. Here we use computational modeling to design a template to direct the formation of an 18-porphyrin nanoring with direct meso-meso bonds between the porphyrin units. Coupling of a linear 18-porphyrin oligomer in the presence of this template gives the target nanoring, together with an unexpected 36-porphyrin ring by-product. Scanning tunneling microscopy (STM) revealed the elliptical conformations and flexibility of these nanorings on a Au(111) surface.

Citation

Van Raden, J. M., Deng, J., Gotfredsen, H., Hergenhahn, J., Clarke, M., Edmondson, M., Hart, J., O'Shea, J. N., Duarte, F., Saywell, A., & Anderson, H. L. (2024). Template‐Directed Synthesis of Strained meso‐meso‐Linked Porphyrin Nanorings. Angewandte Chemie, 136(14), Article e202400103. https://doi.org/10.1002/ange.202400103

• Journal Article Type: Article
• Acceptance Date: Jan 17, 2024
• Publication Date: Apr 2, 2024
• Deposit Date: Jun 2, 2025
• Publicly Available Date: Jun 3, 2025
• Journal: Angewandte Chemie
• Print ISSN: 0044-8249
• Electronic ISSN: 1521-3757
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 136
• Issue: 14
• Article Number: e202400103
• DOI: https://doi.org/10.1002/ange.202400103
• Keywords: porphyrinoids, nanorings, templates, scanning probe microscopy, oligomers
• Public URL: https://nottingham-repository.worktribe.com/output/49857727
• Publisher URL: https://onlinelibrary.wiley.com/doi/10.1002/ange.202400103
• Additional Information: Received: 2024-01-02; Published: 2024-03-01