What question did this study set out to answer?

The aim is to explore the surface modification of cyclobutene-functionalized self-assembled monolayers.

April 1, 2026ChemistryOpen0 citationsOpen Access

Site‐Specific Surface Modification via Chemoselective Click Reactions on Cyclobutene‐Functionalized Monolayers

BEBoone W. EvansUniversity of Nebraska–Lincoln KHKenneth N. HippUniversity of Nebraska–Lincoln WLW. Scott LambertUniversity of Nebraska–Lincoln

Key Points

The aim is to explore the surface modification of cyclobutene-functionalized self-assembled monolayers.
Synthesis of self-assembled monolayers using cyclobutene-substituted alkanethiols on gold surfaces
Application of inverse electron-demand Diels-Alder reactions for monolayer modification
Utilization of both sequential and simultaneous IEDDA and copper-assisted alkyne/azide cycloaddition processes
Successful formation of mixed self-assembled monolayers with cyclobutene and azide functionalities
Demonstrated controlled bisfunctionalization of monolayers
Modified surfaces exhibited enhanced reactivity and potential for further applications

Abstract

We report the first example of self-assembled monolayers (SAMs) incorporating a cyclobutene-substituted alkanethiol on a gold surface and the efficient modification of these monolayers via inverse electron-demand Diels-Alder (IEDDA) cycloadditions. Mixed SAMs incorporating both cyclobutene- and azide-substituted alkane thiols undergo controlled bisfunctionalization through either sequential or simultaneous performance of IEDDA and copper-assisted alkyne/azide cycloaddition (CuAAC) ligations.

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