Facile and general preparation of multifunctional main-chain cationic polymers through application of robust, efficient, and orthogonal click chemistries.

@article{Saha2012FacileAG,
  title={Facile and general preparation of multifunctional main-chain cationic polymers through application of robust, efficient, and orthogonal click chemistries.},
  author={Animesh Saha and Swati De and Mihaiela C. Stuparu and Anzar Khan},
  journal={Journal of the American Chemical Society},
  year={2012},
  volume={134 41},
  pages={
          17291-7
        }
}
Poly(ß-hydroxyl amine)s are prepared from readily available small molecular building blocks at ambient conditions. These macromolecules can be transformed into main-chain cationic polymers upon quaternization of the backbone amine units. The modular and mild nature of the synthesis allows for incorporation of multiple (2-4) chemically distinct reactive sites in the polymer chain. Modifications of the reactive sites afford multifunctional polymers with tunable properties. The orthogonal nature… 

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References

SHOWING 1-10 OF 76 REFERENCES

Structurally diverse dendritic libraries : A highly efficient functionalization approach using Click chemistry

The high fidelity and efficiency of Click chemistry are exploited in the synthesis of a library of chain end functionalized dendritic macromolecules, demonstrating an evolving synergy between advanced organic chemistry and functional materials.

Orthogonal approaches to the simultaneous and cascade functionalization of macromolecules using click chemistry.

These single-step strategies for preparing multifunctional macromolecules represent a significant advance as compared to traditional multistep approaches, and the utility of these concepts is demonstrated by selective preparation of a diverse range of orthogonally functionalized vinyl polymers.

Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "click" chemistry.

Dendrimers up to the fourth generation were successfully prepared via the divergent growth strategy using a combination of thiol-ene "click" chemistry and traditional esterification reactions to functionalize with carboxylic acid, pyrene, and Fmoc-protected cysteine moieties via thiol -ene reactions.

“Click” Chemistry as a Promising Tool for Side-Chain Functionalization of Polyurethanes

1H NMR and FTIR proved the presence of these functional groups and the ability for the introduction of an elevated and controllable amount of functional groups that do not interfere with the PU chemistry.

Modular Covalent Multifunctionalization of Copolymers

A one-pot dual functionalization strategy is presented that allows for the quantitative dualfunctionalization of copolymers and is introduced for the preparation of multifunctional macromolecules.

Facile access to internally functionalized dendrimers through efficient and orthogonal click reactions.

A simple synthetic strategy has been developed for accessing internally functionalized dendrimers using the use of two orthogonal and efficient reactions--'epoxy-amine' and 'thiol-ene' coupling--for rapid growth of the dendritic scaffold.

A versatile new monomer family: functionalized 4-vinyl-1,2,3-triazoles via click chemistry.

Using facile, highly modular synthetic approaches, a new monomer family based on a 1,2,3-triazole-4-vinyl building block has been prepared, and various functional derivatives have been obtained.

Synthesis of functional polymers by post-polymerization modification.

This Review surveys different classes of reactive polymer precursors bearing chemoselective handles and discusses issues related to the preparation of these reactive polymers by direct polymerization of appropriately functionalized monomers as well as the post-polymerization modification of these precursor into functional polymers.

Macromolecular Engineering through Click Chemistry and Other Efficient Transformations

This Perspective provides context as to why these newly developed or recently reinvigorated reactions have been so readily embraced for the preparation of polymers with advanced macromolecular topologies, increased functionality, and unique properties.
...