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Dual‐Responsive Material Based on Catechol‐Modified Self‐Immolative Poly(Disulfide) Backbones
Author(s) -
Agergaard Asger Holm,
Sommerfeldt Andreas,
Pedersen Steen Uttrup,
Birkedal Henrik,
Daasbjerg Kim
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202108698
Subject(s) - chemistry , dithiothreitol , catechol , depolymerization , thiol , covalent bond , polymer , polymer chemistry , cysteine , supramolecular chemistry , dynamic covalent chemistry , combinatorial chemistry , disulfide bond , molecule , organic chemistry , biochemistry , enzyme
Functional materials engineered to degrade upon triggering are in high demand due their potentially lower impact on the environment as well as their use in sensing and in medical applications. Here, stimuli‐responsive polymers are prepared by decorating a self‐immolative poly(dithiothreitol) backbone with pendant catechol units. The highly functional polymer is fashioned into stimuli‐responsive gels, formed through pH‐dependent catecholato–metal ion cross‐links. The gels degrade in response to specific environmental changes, either by addressing the pH responsive, non‐covalent, catecholato–metal complexes, or by addition of a thiol. The latter stimulus triggers end‐to‐end depolymerization of the entire self‐immolative backbone through end‐cap replacement via thiol–disufide exchanges. Gel degradation is visualized by release of a dye from the supramolecular gel as it itself is converted into smaller molecules.