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Switchable Solubility of Azobenzene‐Based Bolaamphiphiles
Author(s) -
Urner Leonhard H.,
Schade Boris,
Schulze Maiko,
Folmert Kristin,
Haag Rainer,
Pagel Kevin
Publication year - 2019
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201900334
Subject(s) - azobenzene , solubility , chemistry , supramolecular chemistry , dissolution , amphiphile , isomerization , chemical engineering , organic chemistry , molecule , copolymer , catalysis , polymer , engineering
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.