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  Switchable Solubility of Azobenzene-Based Bolaamphiphiles

Urner, L. H., Schade, B., Schulze, M., Folmert, K., Haag, R., & Pagel, K. (2019). Switchable Solubility of Azobenzene-Based Bolaamphiphiles. ChemPhysChem, 20(13), 1690-1697. doi:10.1002/cphc.201900334.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0003-BDF4-5 Version Permalink: http://hdl.handle.net/21.11116/0000-0004-C2D0-5
Genre: Journal Article

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 Creators:
Urner, Leonhard H.1, Author
Schade, Boris2, Author
Schulze, Maiko1, Author
Folmert, Kristin1, Author
Haag, Rainer1, Author
Pagel, Kevin1, 3, Author              
Affiliations:
1Freie Universität Berlin, Institute of Chemistry and Biochemistry, Takustraße 3, 14195 Berlin, Germany, ou_persistent22              
2Freie Universität Berlin, Institute of Chemistry and Biochemistry, Research Center of Electron Microscopy, Takustraße 3, 14195 Berlin, Germany, ou_persistent22              
3Molecular Physics, Fritz Haber Institute, Max Planck Society, ou_634545              

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Free keywords: oligoglycerol • bolaamphiphile • azobenzene • water - solubility • supramolecular chemistry
 Abstract: 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.

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Language(s): eng - English
 Dates: 2019-04-052019-05-102019-07-02
 Publication Status: Published online
 Pages: 8
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1002/cphc.201900334
 Degree: -

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Title: ChemPhysChem
Source Genre: Journal
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Publ. Info: Weinheim, Germany : Wiley-VCH
Pages: 8 Volume / Issue: 20 (13) Sequence Number: - Start / End Page: 1690 - 1697 Identifier: ISSN: 1439-4235
CoNE: https://pure.mpg.de/cone/journals/resource/954925409790