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Poly(Ester Amide)S With Pendant Azobenzenes: Multi-Responsive Self-Immolative Moieties For Modulating Polymer Assemblies, Andrew D. Wong, Alex Prinzen, Elizabeth Gillies

Chemistry Publications

Azobenzenes are well-known for their trans–cis photoisomerization, but it was recently demonstrated that azobenzene derivatives could also undergo reduction to trigger a 1,6-elimination and initiate de- polymerization of a self-immolative polymer. Herein we explore the optimization of azobenzenes as reduction-sensitive moieties, and their incorporation into functional materials. A library of azobenzenes with electron-withdrawing groups was synthesized, and their rates of reduction by hydrazine were deter- mined. Unexpectedly, a 2-Cl substituent increased the rate of reduction more than other electronegative or sterically-demanding substituents. Next, a new diester monomer containing the 2-Cl-azobenzene was synthesized and incorporated into a poly(ester amide) (PEA) backbone, …