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Post-assembly Modification of Tetrazine-Edged FeII4L6 Tetrahedra

DOI: 10.1021/jacs.5b05080 DOI Help

Authors: Derrick A. Roberts (Department of Chemistry, The University of Cambridge, Lensfield Road, Cambridge) , Ben S. Pilgrim (Department of Chemistry, The University of Cambridge, Lensfield Road, Cambridge) , Jonathan D. Cooper , Tanya K. Ronson , Salvatore Zarra , Jonathan R. Nitschke (Department of Chemistry, The University of Cambridge, Lensfield Road, Cambridge)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Journal Of The American Chemical Society , VOL 137 (32)

State: Published (Approved)
Published: August 2015
Diamond Proposal Number(s): 8464

Open Access Open Access

Abstract: Post-assembly modification (PAM) is a powerful tool for the modular functionalization of selfassembled structures. We report a new family of tetrazineedged FeII 4L6 tetrahedral cages, prepared using different aniline subcomponents, which undergo rapid and efficient PAM by inverse electron-demand Diels−Alder (IEDDA) reactions. Remarkably, the electron-donating or -withdrawing ability of the para-substituent on the aniline moiety influences the IEDDA reactivity of the tetrazine ring 11 bonds away. This effect manifests as a linear free energy relationship, quantified using the Hammett equation, between σpara and the rate of the IEDDA reaction. The rate of PAM can thus be adjusted by varying the aniline subcomponent.

Subject Areas: Chemistry


Instruments: I19-Small Molecule Single Crystal Diffraction

Added On: 12/08/2015 12:43

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