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 enhance 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., …Anderson, H. L. (2024). Template‐Directed Synthesis of Strained meso‐meso‐Linked Porphyrin Nanorings. Angewandte Chemie International Edition, Article e202400103. https://doi.org/10.1002/anie.202400103

• Journal Article Type: Article
• Acceptance Date: Jan 17, 2024
• Online Publication Date: Jan 17, 2024
• Publication Date: Jan 17, 2024
• Deposit Date: Mar 12, 2024
• Publicly Available Date: Mar 12, 2024
• Journal: Angewandte Chemie International Edition
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Article Number: e202400103
• DOI: https://doi.org/10.1002/anie.202400103
• Keywords: Porphyrinoids; nanorings; templates; scanning probe microscopy; oligomers
• Public URL: https://nottingham-repository.worktribe.com/output/30926386
• Publisher URL: https://onlinelibrary.wiley.com/doi/10.1002/anie.202400103
• Additional Information: Received: 2024-01-02; Published: 2024-03-01