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Switchable Solubility of Azobenzene-Based Bolaamphiphiles

Urner, L.H.;* Schade, B.; Schulze, M.; Folmert, K.; Haag, R.; Pagel, K.* – 2019

The ability to design amphiphiles with predictable solubility properties is of everlasting interest in supramolecular chemistry. Relevant structural parameters include the hydrophobic–hydrophilic balance and structural flexibility. In this work, we investigate the water solubility of azobenzene‐based triglycerol bolaamphiphiles (TGBAs). In particular, we analyzed the structural effects of backbone hydrophobicity, flexibility, and cis/trans isomerization on the water solubility of a subset of five TGBAs. This leads to the first example of a non‐ionic bolaamphiphile whose water solubility can be changed by irradiation with light. The underlying kinetics were monitored using liquid chromatography and a closer analysis of the underlying aggregation processes provides a mechanistic understanding of the light‐driven dissolution process. We anticipate that the results obtained will help to engineer bolaamphiphiles with predictable solution properties in the future.

Title
Switchable Solubility of Azobenzene-Based Bolaamphiphiles
Author
Urner, L.H.;* Schade, B.; Schulze, M.; Folmert, K.; Haag, R.; Pagel, K.*
Date
2019
Identifier
10.1002/cphc.201900334
Source(s)
Citation
ChemPhysChem 2019, 20, 1690–1697.
Type
Text
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