Click to Self‐immolation: A “Click” Functionalization Strategy towards Triggerable Self‐Immolative Homopolymers and Block Copolymers
Self‐immolative polymers (SIPs) are a class of degradable macromolecules that undergo stimuli‐triggered head‐to‐tail depolymerization. However, a general approach to readily end‐functionalize SIP precursors for programmed degradation remains elusive, restricting access to complex, functional SIP‐bas...
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| Published in | Angewandte Chemie International Edition Vol. 63; no. 3; pp. e202317063 - n/a |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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Germany
Wiley Subscription Services, Inc
15.01.2024
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| Edition | International ed. in English |
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| Abstract | Self‐immolative polymers (SIPs) are a class of degradable macromolecules that undergo stimuli‐triggered head‐to‐tail depolymerization. However, a general approach to readily end‐functionalize SIP precursors for programmed degradation remains elusive, restricting access to complex, functional SIP‐based materials. Here we present a “click to self‐immolation” strategy based on aroyl azide‐capped SIP precursors, enabling the facile construction of diverse SIPs with different trigger units through a Curtius rearrangement and alcohol/thiol‐isocyanate “click” reaction. This strategy is also applied to polymer‐polymer coupling to access fully depolymerizable block copolymer amphiphiles, even combining different SIP backbones. Our results demonstrate that the depolymerization can be actuated efficiently under physiologically‐relevant conditions by the removal of the trigger units and ensuing self‐immolation of the p‐aminobenzyl carbonate linkage, indicating promise for controlled release applications involving nanoparticles and hydrogels.
An efficient “click to self‐immolation” approach based on a Curtius rearrangement and alcohol‐isocyanate reaction was developed to functionalize self‐immolative polymer precursors with varying trigger units and allow polymer‐polymer coupling to access head‐to‐tail depolymerizable block copolymers, which could undergo programmable self‐immolation in response to specified stimuli. |
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| AbstractList | Self‐immolative polymers (SIPs) are a class of degradable macromolecules that undergo stimuli‐triggered head‐to‐tail depolymerization. However, a general approach to readily end‐functionalize SIP precursors for programmed degradation remains elusive, restricting access to complex, functional SIP‐based materials. Here we present a “click to self‐immolation” strategy based on aroyl azide‐capped SIP precursors, enabling the facile construction of diverse SIPs with different trigger units through a Curtius rearrangement and alcohol/thiol‐isocyanate “click” reaction. This strategy is also applied to polymer‐polymer coupling to access fully depolymerizable block copolymer amphiphiles, even combining different SIP backbones. Our results demonstrate that the depolymerization can be actuated efficiently under physiologically‐relevant conditions by the removal of the trigger units and ensuing self‐immolation of the p‐aminobenzyl carbonate linkage, indicating promise for controlled release applications involving nanoparticles and hydrogels.
An efficient “click to self‐immolation” approach based on a Curtius rearrangement and alcohol‐isocyanate reaction was developed to functionalize self‐immolative polymer precursors with varying trigger units and allow polymer‐polymer coupling to access head‐to‐tail depolymerizable block copolymers, which could undergo programmable self‐immolation in response to specified stimuli. Self-immolative polymers (SIPs) are a class of degradable macromolecules that undergo stimuli-triggered head-to-tail depolymerization. However, a general approach to readily end-functionalize SIP precursors for programmed degradation remains elusive, restricting access to complex, functional SIP-based materials. Here we present a "click to self-immolation" strategy based on aroyl azide-capped SIP precursors, enabling the facile construction of diverse SIPs with different trigger units through a Curtius rearrangement and alcohol/thiol-isocyanate "click" reaction. This strategy is also applied to polymer-polymer coupling to access fully depolymerizable block copolymer amphiphiles, even combining different SIP backbones. Our results demonstrate that the depolymerization can be actuated efficiently under physiologically-relevant conditions by the removal of the trigger units and ensuing self-immolation of the p-aminobenzyl carbonate linkage, indicating promise for controlled release applications involving nanoparticles and hydrogels. Self‐immolative polymers (SIPs) are a class of degradable macromolecules that undergo stimuli‐triggered head‐to‐tail depolymerization. However, a general approach to readily end‐functionalize SIP precursors for programmed degradation remains elusive, restricting access to complex, functional SIP‐based materials. Here we present a “click to self‐immolation” strategy based on aroyl azide‐capped SIP precursors, enabling the facile construction of diverse SIPs with different trigger units through a Curtius rearrangement and alcohol/thiol‐isocyanate “click” reaction. This strategy is also applied to polymer‐polymer coupling to access fully depolymerizable block copolymer amphiphiles, even combining different SIP backbones. Our results demonstrate that the depolymerization can be actuated efficiently under physiologically‐relevant conditions by the removal of the trigger units and ensuing self‐immolation of the p ‐aminobenzyl carbonate linkage, indicating promise for controlled release applications involving nanoparticles and hydrogels. |
| Author | Liang, Xiaoli Gillies, Elizabeth R. Deng, Zhengyu |
| Author_xml | – sequence: 1 givenname: Zhengyu orcidid: 0000-0002-7186-7491 surname: Deng fullname: Deng, Zhengyu organization: The University of Western Ontario – sequence: 2 givenname: Xiaoli surname: Liang fullname: Liang, Xiaoli organization: The University of Western Ontario – sequence: 3 givenname: Elizabeth R. orcidid: 0000-0002-3983-2248 surname: Gillies fullname: Gillies, Elizabeth R. email: egillie@uwo.ca organization: The University of Western Ontario |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38029347$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1021_acs_chemmater_4c00583 crossref_primary_10_1002_adhm_202304599 |
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| Keywords | Stimuli-Responsive Block Copolymer Functionalization Self-Immolative Polymer Click Chemistry |
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| Snippet | Self‐immolative polymers (SIPs) are a class of degradable macromolecules that undergo stimuli‐triggered head‐to‐tail depolymerization. However, a general... Self-immolative polymers (SIPs) are a class of degradable macromolecules that undergo stimuli-triggered head-to-tail depolymerization. However, a general... |
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| SubjectTerms | Block Copolymer Block copolymers Click Chemistry Controlled release Depolymerization Functionalization Isocyanates Macromolecules Nanoparticles Polymers Precursors Self-Immolative Polymer Stimuli-Responsive |
| Title | Click to Self‐immolation: A “Click” Functionalization Strategy towards Triggerable Self‐Immolative Homopolymers and Block Copolymers |
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