TEC and TYC Reaction Synthesis Strategy for Dendrimers

Thiol-ene and thiol-yne click (TEC/TYC) reactions combine the advantages of click reactions and is widely used in the field of dendrimer-related polymers. With advanced technology and experienced scientists, CD BioSciences offers you TEC/TYC reaction synthesis services for dendrimers.

Click Chemistry and TEC/TYC Reaction

As an ideal sustainable synthesis of polymers, click chemistry reactions are characterized by high efficiency, atomic economy, and single reaction trajectories, which can expand the structural scope of accessible polymers from sustainably sourced chemicals. Click chemistry can be applied to many fields such as drug development and biomedical materials and has become one of the most useful and attractive chemical synthesis methods. There are many chemical synthesis methods based on click chemistry, such as CuAAC reaction, TEC/TYC reaction and DA reaction, among others. Among them, TEC/TYC is a straightforward technique for producing high-molecular-weight step-growth polymers in an exceedingly efficient manner and can be performed at ambient temperature.

General schemes for TEC (Top) and for TYC reaction (Bottom). (Arseneault M, et al., 2015)

Advantages and Applications of TEC/TYC Reaction

TEC/TYC combines the advantages of click reactions, offering regiospecificity, stereospecificity, mild reaction conditions, high yields, and can be activated by thermal or photochemical processes, at selected times and locations, in a process that does not require heavy-metal catalysts. TEC/TYC is widely used in the synthesis of dendrimers, polymer functionalization, particle modification, protein conjugation, microarray fabrication, functional silanes and difunctionalization of materials.

TEC/TYC Reaction Synthesis for Dendrimers

• TEC

TEC has attracted a great deal of attention in the last few decades and was discovered in the mid-19th century, with a more diffuse origin than CuAAC. TEC plays an extremely important role in biological systems because of its many benefits in materials synthesis and thiol group conjugation. In its current form, TEC consists of a reaction between a terminal alkene and a thiol, which can proceed via either a free-radical mechanism or a nucleophilic one. The former is the most popular, as it can be photocatalyzed. Although TEC is relatively new and less popular than CuAAC, it now has a place in the materials chemist's toolbox.

• TYC

Click-step polymerization using TYC, a reaction first reported over a century ago, has emerged as an extremely mild and atom-efficient pathway to yield high-performance polymers. TYC works through the same mechanism as TEC. The difference is that once a thiol fragment has linked to the alkyne, a second reaction can occur on the resulting alkene. TYC is much more difficult to control in terms of regioselectivity, even more so if one aims to prevent the addition of the second thiol. However, this challenge is almost irrelevant in dendritic polymers because scientists have mainly used TYC for molecular strategies in dendritic macromolecules.

Nucleophilic and radical mechanisms for thiol addition to alkenes and alkynes (left) and nucleophilic TEC/TYC polymerization to afford step-growth polymers with well-defined stereochemistry (right). (Worch JC, et al., 2022)

Our Services

CD BioSciences offers click chemistry-based dendrimer TEC and TYC reaction synthesis services and guarantee that all deliverables undergo rigorous quality testing to ensure quality and reliability and are delivered on time.

What We Provide

Service Process

As a leading global provider of custom services, CD BioSciences has advanced facilities and experienced scientists to synthesize a variety of dendrimers through click chemistry synthesis methods such as CuAAC, TEC/TYC reactions, DA reactions, and other click chemistry-based methods to help our customers advance their downstream applications of dendrimers. If you are interested in our services or have any other questions, please feel free to contact us, we would be happy to hear from you and look forward to working with you.

References

1. Arseneault M.; et al. Recent advances in click chemistry applied to dendrimer synthesis. Molecules. 2015, 20: 9263-94.
2. Worch JC, Dove AP. Click Step-Growth Polymerization and E/Z Stereochemistry Using Nucleophilic Thiol-yne/-ene Reactions: Applying Old Concepts for Practical Sustainable (Bio)Materials. Acc Chem Res. 2022, 55:2355-2369.