Related Experiment Video
Updated: Dec 29, 2025

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
Published on: August 2, 2012
Hexayne Amphiphiles and Bolaamphiphiles.
Enzo Bomal1, Vincent Croué1, Reuben Yeo1
1Institute of Materials, Laboratory of Macromolecular and Organic Materials, Ecole Polytechnique Fédérale de Lausanne (EPFL), MXG 135, Station 12, 1015, Lausanne, Switzerland.
Researchers developed a universal synthesis for functionalized hexaynes, enabling the creation of carbon-rich amphiphiles. These molecules self-assemble at interfaces and in solution, expanding applications for nanomaterials.
Area of Science:
- Organic Chemistry
- Materials Science
- Nanotechnology
Background:
- Oligoynes with conjugated carbon-carbon triple bonds are valuable precursors for carbon-rich nanomaterials.
- The synthesis of functionalized oligoynes remains challenging, limiting their applications.
Purpose of the Study:
- To develop a universal synthetic approach for functionalized hexaynes.
- To explore the self-assembly properties of these novel carbon-rich molecules.
Main Methods:
- Modified Eglinton-Galbraith coupling reaction.
- Utilized a sacrificial building block strategy.
- Synthesized hexaynes with phosphonic acid, carboxylic acid, ammonium, and thiol head groups.
Main Results:
- Successfully synthesized symmetric and unsymmetric functionalized hexaynes.
- Created hexaynes with neutral, cationogenic, and anionogenic interfacial properties.
- Demonstrated self-assembly of hexaynes at liquid-liquid interfaces, solid surfaces, and in aqueous media.
Conclusions:
- The developed synthetic approach provides versatile access to functionalized hexaynes.
- These hexaynes act as carbon-rich amphiphiles and bolaamphiphiles with self-assembly capabilities.
- The findings open new avenues for designing advanced carbon-rich nanomaterials.
Related Concept Videos
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Ion Exchange
Structure of Amines
Nomenclature of Alkynes
Nucleophiles
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...

