Dynamic Imine Chemistry at Complex Double Emulsion Interfaces
Name
doi-10.1021 jacs.9b06852.pdf
Description
Accepted version
Size
852.04 KB
Format
Adobe PDF
Checksum (MD5)
7411e4e5529a465a793cd98ed7582d59
Author(s)
Zentner, Cassandra Aileen
Anson, Francesca
Thayumanavan, S.
Swager, Timothy M
Date Issued
November 2019
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Zentner, Cassandra A. et al. "Dynamic Imine Chemistry at Complex Double Emulsion Interfaces." Journal of the American Chemical Society 141, 45 (November 2019): 18048–18055 © 2019 American Chemical Society
Version
Author's final manuscript
Abstract
Interfacial chemistry provides an opportunity to control dynamic materials. By harnessing the dynamic covalent nature of imine bonds, emulsions are generated in situ, predictably manipulated, and ultimately destroyed along liquid-liquid and emulsion-solid interfaces through simple perturbation of the imine equilibria. We report the rapid production of surfactants and double emulsions through spontaneous in situ imine formation at the liquid-liquid interface of oil/water. Complex double emulsions with imine surfactants are stable to neutral and basic conditions and display dynamic behavior with acid-catalyzed hydrolysis and imine exchange. We demonstrate the potential of in situ imine surfactant formation to generate complex surfactants with biomolecules (i.e., antibodies) for biosensing applications. Furthermore, imine formation at the emulsion-solid interface offers a triggered payload release mechanism. Our results illustrate how simple, dynamic interfacial imine formation can translate changes in bonding to macroscopic outputs.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
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DOI of Published Version
https://doi.org/10.1021/jacs.9b06852
