Tuning the Reactivity of Micellar Nanoreactors by Precise Adjustments of the Amphiphile and Substrate Hydrophobicity

• DOI: 10.1021/acs.macromol.1c01755
• Publication Date: 2021-12-01T08:33:59Z
• Authors: Shahar Tevet; Shreyas S. Wagle; Gadi Slor; Roey J. Amir
• Keywords: Nanoreactor; Lipophilicity; Micellar solutions

Polymeric assemblies, such as micelles, are gaining increasing attention due to their ability serve nanoreactors for the execution of organic reactions in aqueous media. The conduct transformations, which have been traditionally limited media, water is essential further development important fields ranging from green catalysis bioorthogonal chemistry. Considering recent progress that has made expand range organometallic conducted using nanoreactors, we aimed gain a deeper understanding roles hydrophobicity both core micellar and substrates on reaction rates water. Toward this goal, designed set five metal-loaded micelles composed polyethylene glycol–dendron amphiphiles studied palladium-mediated depropargylation four with different log P values. Using dendrons hydrophobic block, could precisely tune lipophilicity allowed us reveal linear correlations between rate constants (estimated by dendron's cLog P). While exponential dependence was obtained substrates, similar degree acceleration observed increase regardless effect substrate's P. Our results demonstrate while may be used accelerate rates, tuning can vital tool optimization reactivity selectivity nanoreactors.