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… 
View on PubMed
doi.org
75 Citations
Background Citations
3
Methods Citations
1

Figures from this paper

75 Citations

Multiply functionalized dendrimers: protective-group-free synthesis through sequential thiol-epoxy ‘click’ chemistry and esterification reaction

A modular synthetic strategy is described for the preparation of multiply functionalized dendrimers that allows for placement of chemically different moieties at different dendritic layers.

Clickable Poly(ionic liquids): A Materials Platform for Transfection.

A post-polymerization click reaction is reported that provides facile access to trisaminocyclopropenium (TAC) ion-functionalized macromolecules of various architectures, which are the first class of polyelectrolytes that bear a formal charge on carbon.

A Modular and Practical Synthesis of Zwitterionic Hydrogels through Sequential Amine-Epoxy “Click” Chemistry and N-Alkylation Reaction

The amine-epoxy “click” reaction is shown to be a valuable general tool in the synthesis of reactive hydrogels and can be combined with soft lithography techniques such as micromolding in capillaries to obtain hydrogel microstructures.

Thermoresponsive Poly(ß-hydroxyl amine)s: Synthesis of a New Stimuli Responsive Amphiphilic Homopolymer Family through Amine-Epoxy ‘Click’ Polymerization

The modularity of the synthesis allows for facile structural modulation and tuning of the thermally triggered aggregation process in the temperature range of 7 to 91 °C, and the underlying principles can be translated from linear architectures to polymer networks (hydrogels).

Addressing the mid-point of polymer chains for multiple functionalization purposes through sequential thiol–epoxy ‘click’ and esterification reactions

A synthetic strategy is devised for the preparation of mid-chain multifunctional polymers. In this strategy, small molecules carrying one or two epoxide units along with two polymerization-initiating…

Synthesis of multifunctional homopolymers via sequential post-polymerization reactions

Multifunctional homopolymers, homopolymers with multiple pendent functionalities, can offer unparalleled properties not possible with traditional polymers. Preparation of multifunctional homopolymers…

Multifunctional Homopolymers: Postpolymerization Modification via Sequential Nucleophilic Aromatic Substitution

Despite recent progress for efficient and precise synthesis of functional polymers, few reports describe postpolymerization functionalization strategies for the controlled incorporation of multiple…

Sequential Thiol-Epoxy and Esterification Reactions: A Facile Route to Bifunctional Homopolymer Sequences

A post-polymerization double-modification strategy involving sequential thiol-epoxy and esterification reactions is discussed for the preparation of bifunctionalized homopolymer sequences and their application in the arena of siRNA delivery are discussed.

Scalable ambient synthesis of water-soluble poly(β-hydroxythio-ether)s

Proton transfer polymerization through thiol-epoxy “click” reaction between commercially available and hydrophilic di-thiol and di-epoxide monomers is carried out under ambient conditions to furnish…

Scalable synthesis and derivation of functional polyesters bearing ene and epoxide side chains

A scalable library of functional polyesters based on the polymerization of trimethylolpropane allyl ether with diacid chlorides with structural similarity to established non-functional polyesters such as PLGA may find broad application as functional polyester for gene delivery, tissue engineering, and other nanotechnology applications.
...

75 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.

Synthetic polymers with quaternary nitrogen atoms—Synthesis and structure of the most used type of cationic polyelectrolytes

“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.
...