Click to Self-immolation: A "Click" Functionalization Strategy towards Triggerable Self-Immolative Homopolymers and...

Area of Science:

• Polymer Chemistry
• Materials Science
• Organic Chemistry

Background:

• Self-immolative polymers (SIPs) are degradable macromolecules that depolymerize in response to stimuli.
• Current methods for end-functionalizing SIP precursors are limited, hindering the creation of complex, functional SIP-based materials.

Purpose of the Study:

• To develop a general and facile strategy for end-functionalizing self-immolative polymer precursors.
• To enable the construction of diverse SIPs with tailored trigger units and functionalities.
• To explore the application of this strategy in creating fully depolymerizable block copolymers.

Main Methods:

• A
• click to self-immolation
• strategy was developed using aroyl azide-capped SIP precursors.
• This involved a Curtius rearrangement followed by an alcohol/thiol-isocyanate
• click
• reaction.
• The method was applied to polymer-polymer coupling for block copolymer synthesis.

Main Results:

• The
• click to self-immolation
• strategy successfully enabled the facile synthesis of diverse SIPs with various trigger units.
• Fully depolymerizable block copolymer amphiphiles were synthesized, even combining different SIP backbones.
• Depolymerization was efficiently triggered under physiologically relevant conditions via removal of trigger units and subsequent self-immolation of the p-aminobenzyl carbonate linkage.

Conclusions:

• The developed
• click to self-immolation
• strategy provides a versatile platform for creating functional self-immolative polymers.
• This approach facilitates the design of advanced degradable materials with programmed degradation capabilities.
• The findings show significant promise for applications in controlled release systems, including nanoparticles and hydrogels.