Jump to main content
Jump to site search


Dendritic architectures by orthogonal thiol-maleimide “click” and furan-maleimide dynamic covalent chemistries

Author affiliations

Abstract

A set of dendrons and dendrimers is synthesized divergently using an orthogonal combination of kinetically-driven thiol-maleimide “click” chemistry and thermodynamically reversible furan-maleimide cycloaddition/retrocycloaddition reactions. Growth is controlled by taking advantage of the selective thiol–ene addition of thiols to the electron withdrawn alkene of maleimide in the presence of electron rich alkene of oxanorbornene. Subsequent activation of growing dendrons/dendrimers requires only heat to induce the dynamic covalent liberation of peripheral furan protecting groups. The methodology introduced provides a new route to multifunctional dendrimers that could, in principle, be synthesized by introducing different branched monomers at any stage of dendrimer growth, allowing dendrimer architectures and properties to be better tailored to their intended applications.

Graphical abstract: Dendritic architectures by orthogonal thiol-maleimide “click” and furan-maleimide dynamic covalent chemistries

Back to tab navigation

Supplementary files

Publication details

The article was received on 28 Jun 2019, accepted on 05 Aug 2019 and first published on 05 Aug 2019


Article type: Communication
DOI: 10.1039/C9OB01459D
Org. Biomol. Chem., 2019, Advance Article

  •   Request permissions

    Dendritic architectures by orthogonal thiol-maleimide “click” and furan-maleimide dynamic covalent chemistries

    S. H. Frayne, R. M. Stolz and B. H. Northrop, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01459D

Search articles by author

Spotlight

Advertisements