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Erschienen in:
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2013 | OriginalPaper | Buchkapitel

Supramolecular Chromaticity and Thermoresponsive Hydrogels: A Self-Assembly Study on Maleamic Acid-Based Amphiphiles

verfasst von : Andreas Bernet, Marina Behr, Rodrigo Q. Albuquerque, Marko Schmidt, Jürgen Senker, Hans-Werner Schmidt

Erschienen in: Intelligent Hydrogels

Verlag: Springer International Publishing

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Abstract

A new class of homologous low molecular weight amphiphiles based on maleamic acid was synthesized and investigated in terms of its self-assembly behavior in bulk and in solution. The unexpected yellow color as bulk material and in organic solvents was revealed by means of spectroscopic and theoretical investigations to originate from intermolecular π-π interactions yielding supramolecular chromophores. It was found that the length of the alkyl chain of the amphiphiles and the resulting hydrophilic/lipophilic balance dictates the aggregation mode in bulk. One special compound exhibiting an n-tetradecyl chain was found to form stable thermoreversible supramolecular hydrogels in aqueous sodium hydroxide solutions. The corresponding hydrogels feature a rare cellular bilayer-based morphology and can be transferred into viscoelastic solutions upon heating and vice versa.

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Nächstes Kapitel Thermo-responsive Amphiphilic Di- and Triblock Copolymers Based on Poly(N-isopropylacrylamide) and Poly(methoxy diethylene glycol acrylate): Aggregation and Hydrogel Formation in Bulk Solution and in Thin Films
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Fußnoten
1
Only molecule peak (m ∙+) and peaks with relative intensities ≥ 10 % are listed in the corresponding characterization datasets for compounds 1–6.
 
2
The multiplicity of this signal cannot be determined as it is covered by the signal of DMSO. However, the presence of this peak can be proven by HH-COSY NMR experiments. This is also the case for compounds2–6.
 
3
5 has been favored over 6 that features the longest alkyl chain because the former shows higher solubilities in organic media.
 
4
The hydrogel samples prepared from 5 in aq. NaOH sol. can be stored under ambient conditions for more than a year without any recognizable decomposition.
 
5
It has to be noted that solutions of 5 in aq. NaOH sol. at elevated temperatures as well as hydrogels of 5 (where in both cases 5 is transformed in situ into the corresponding sodium carboxylate 5Na) do not show any color. In contrast, a comparable sample of 1 in aq. NaOH sol. (1Na) exhibits a pale yellow color. We explain this by a strong difference of the HLB that leads to different favored aggregation modes of the corresponding sodium carboxylates 1Na and 5Na (π-π vs. van der Waals interactions).
 
6
The onset of the melting peak of the μDSC traces is in good agreement with macroscopically observed gel melting at ca. 35–36 °C (“falling steel ball method”, ca. 1 °C min−1).
 
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Metadaten
Titel
Supramolecular Chromaticity and Thermoresponsive Hydrogels: A Self-Assembly Study on Maleamic Acid-Based Amphiphiles
verfasst von
Andreas Bernet
Marina Behr
Rodrigo Q. Albuquerque
Marko Schmidt
Jürgen Senker
Hans-Werner Schmidt
Copyright-Jahr
2013
Buch
Intelligent Hydrogels

Print ISBN: 978-3-319-01682-5

Electronic ISBN: 978-3-319-01683-2

Copyright-Jahr: 2013

DOI
https://doi.org/10.1007/978-3-319-01683-2_1

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