Related Experiment Video
Updated: Mar 31, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Site-Specific Surface Modification via Chemoselective Click Reactions on Cyclobutene-Functionalized Monolayers
Boone W Evans1, Kenneth N Hipp1, William D Lambert1
1Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska, USA.
This study introduces self-assembled monolayers with cyclobutene for surface modification. These monolayers enable efficient chemical reactions, allowing for controlled bisfunctionalization via Diels-Alder and click chemistry.
Area of Science:
- Surface chemistry
- Organic chemistry
- Materials science
Background:
- Self-assembled monolayers (SAMs) are crucial for surface functionalization.
- Cyclobutene moieties offer unique reactivity for chemical modifications.
- Gold surfaces are widely used platforms for SAMs.
Purpose of the Study:
- To report the first SAMs incorporating cyclobutene-substituted alkanethiols on gold.
- To demonstrate efficient monolayer modification using inverse electron-demand Diels-Alder (IEDDA) cycloadditions.
- To achieve controlled bisfunctionalization of mixed SAMs.
Main Methods:
- Formation of SAMs on gold surfaces using cyclobutene- and azide-substituted alkanethiols.
- Application of inverse electron-demand Diels-Alder (IEDDA) cycloadditions for surface modification.
- Utilizing copper-assisted alkyne/azide cycloaddition (CuAAC) ligation for bisfunctionalization.
Main Results:
- Successful incorporation of cyclobutene-substituted alkanethiols into SAMs on gold.
- Efficient modification of these SAMs via IEDDA cycloadditions.
- Demonstrated controlled bisfunctionalization of mixed SAMs using sequential or simultaneous IEDDA and CuAAC reactions.
Conclusions:
- This work presents a novel approach for creating functionalized surfaces using cyclobutene-containing SAMs.
- The developed method allows for precise control over surface modification through orthogonal click chemistry reactions.
- These findings open new avenues for advanced materials and surface engineering.
More Related Videos
08:12Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance
Published on: September 5, 2018
14:43Microfluidic On-chip Capture-cycloaddition Reaction to Reversibly Immobilize Small Molecules or Multi-component Structures for Biosensor Applications
Published on: September 23, 2013
Related Concept Videos
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry