Pathway-Dependent Post-assembly Modification of an Anthracene-Edged MII4L6 Tetrahedron

Ronson, Tanya K.; Pilgrim, Ben S.; Nitschke, Jonathan R.

Abstract

FeII4L6 tetrahedral cage 1 undergoes post-assembly modification (PAM) via a Diels–Alder cycloaddition of the anthracene panels of the cage with tetracyanoethylene (TCNE). The modified cage 2 possesses an enclosed cavity suitable for encapsulation of the fullerene C60, whereas original cage 1 forms a unique covalent adduct through a Diels–Alder cycloaddition of three of its anthracene ligands with C60. This adduct undergoes further PAM via reaction of the remaining three ligands with TCNE, enabling the isolation of two distinct products depending on the order of addition of C60 and TCNE. Modified cage 2 was also able to bind an anionic guest, [Co(C2B9H11)2]−, which was not encapsulated by the original cage, demonstrating the potential of PAM for tuning the binding properties of supramolecular hosts.

Citation

Ronson, T. K., Pilgrim, B. S., & Nitschke, J. R. (2016). Pathway-Dependent Post-assembly Modification of an Anthracene-Edged MII4L6 Tetrahedron. Journal of the American Chemical Society, 138(33), 10417-10420. https://doi.org/10.1021/jacs.6b06710

• Journal Article Type: Article
• Acceptance Date: Aug 8, 2016
• Online Publication Date: Aug 16, 2016
• Publication Date: Aug 24, 2016
• Deposit Date: Feb 24, 2020
• Publicly Available Date: May 6, 2020
• Journal: Journal of the American Chemical Society
• Print ISSN: 0002-7863
• Electronic ISSN: 1520-5126
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 138
• Issue: 33
• Pages: 10417-10420
• DOI: https://doi.org/10.1021/jacs.6b06710
• Public URL: https://nottingham-repository.worktribe.com/output/4026274
• Publisher URL: https://pubs.acs.org/doi/10.1021/jacs.6b06710