Pathway-Dependent Post-assembly Modification of an Anthracene-Edged M(II)4L6 Tetrahedron

Tanya K Ronson; Ben S Pilgrim; Jonathan R Nitschke

doi:10.1021/jacs.6b06710

Pathway-Dependent Post-assembly Modification of an Anthracene-Edged M(II)4L6 Tetrahedron

J Am Chem Soc. 2016 Aug 24;138(33):10417-20. doi: 10.1021/jacs.6b06710. Epub 2016 Aug 16.

Authors

Tanya K Ronson¹, Ben S Pilgrim¹, Jonathan R Nitschke¹

Affiliation

¹ Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.

PMID: 27500974
DOI: 10.1021/jacs.6b06710

Abstract

Fe(II)4L6 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.

Publication types

Research Support, Non-U.S. Gov't