Related Experiment Video
Updated: Jun 12, 2026

Fabrication of Three-Dimensional Graphene-Based Polyhedrons via Origami-Like Self-Folding
Published on: September 23, 2018
Functionalization of graphene via 1,3-dipolar cycloaddition
Mildred Quintana1, Konstantinos Spyrou, Marek Grzelczak
1Center of Excellence for Nanostructured Materials (CENMAT) and INSTM, Unit of Trieste, Dipartimento di Scienze Farmaceutiche, University of Trieste, Piazzale Europa 1, I-34127 Trieste, Italy.
Few-layer graphene (FLG) was successfully functionalized with amino groups, which selectively bind to gold nanorods. This demonstrates FLG
Area of Science:
- Materials Science
- Nanotechnology
- Organic Chemistry
Background:
- Few-layer graphene (FLG) is derived from graphite via exfoliation.
- Functionalization of graphene is crucial for its application in advanced materials.
- Understanding graphene's reactivity is key to controlling its properties.
Purpose of the Study:
- To functionalize few-layer graphene (FLG) using 1,3-dipolar cycloaddition.
- To investigate the selective binding of gold nanorods to functionalized graphene.
- To confirm the location and extent of functionalization on graphene sheets.
Main Methods:
- Exfoliation of graphite in N-methylpyrrolidone to produce FLG.
- Functionalization of FLG using azomethine ylide 1,3-dipolar cycloaddition.
- Kaiser test for amino group quantification, UV-vis spectroscopy, XPS, TGA, and TEM for characterization.
Main Results:
- Successful attachment of amino groups to FLG, quantified by Kaiser test.
- Selective binding of gold nanorods to amino-functionalized graphene sites.
- Uniform distribution of gold nanorods across graphene sheets, indicating internal C horizontal lineC bond reactivity.
Conclusions:
- Exfoliated few-layer graphene is significantly more reactive than graphite.
- Functionalization occurs on both edges and internal sites of graphene.
- Controlled functionalization of graphene opens possibilities for composite nanomaterials.
Related Concept Videos
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are formed faster owing to...

