Wedge‐Shaped Molecules with a Sulfonate Group at the Tip—A New Class of Self‐Assembling Amphiphiles
Identifieur interne : 003136 ( Main/Merge ); précédent : 003135; suivant : 003137Wedge‐Shaped Molecules with a Sulfonate Group at the Tip—A New Class of Self‐Assembling Amphiphiles
Auteurs : Xiaomin Zhu ; Bernd Tartsch [Allemagne] ; Uwe Beginn [Allemagne] ; Martin Möller [Allemagne]Source :
- Chemistry – A European Journal [ 0947-6539 ] ; 2004-08-20.
Abstract
The synthesis of 4‐N‐[3′,4′,5′‐tris(dodecyloxy)benzamido]benzene‐4‐sulfonic acid (1) and 4′‐[3′′,4′′,5′′‐tris(dodecyloxy)benzoyloxy]azobenzene‐4‐sulfonic acid (2) is described. Pure acid 1 is stable, while 2 can be stored only in solution. Both acids were obtained from their sodium salts and were quantitatively transformed into the pyridinium salts. The phase behavior of these acids, as well as the sulfonates was investigated by differential scanning calorimetry and polarizing optical microscopy. The investigated compounds exhibit columnar mesophases. The formation of columnar superstructures was demonstrated for the sodium sulfonates by scanning force microscopy, gelation experiments, and proton magnetic resonance spectroscopy.
Wedge‐shaped sulfonate amphiphiles self‐assemble in bulk and from solution to give rodlike structures with circular cross‐sections (see picture); this causes the formation of columnar mesophases, as well as gelation of the solution. Phase diagram investigations demonstrate that the transition from the gel state to the highly ordered bulk phase occurs through a lyotropic mesophase.
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DOI: 10.1002/chem.200400050
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<front><div type="abstract" xml:lang="en">The synthesis of 4‐N‐[3′,4′,5′‐tris(dodecyloxy)benzamido]benzene‐4‐sulfonic acid (1) and 4′‐[3′′,4′′,5′′‐tris(dodecyloxy)benzoyloxy]azobenzene‐4‐sulfonic acid (2) is described. Pure acid 1 is stable, while 2 can be stored only in solution. Both acids were obtained from their sodium salts and were quantitatively transformed into the pyridinium salts. The phase behavior of these acids, as well as the sulfonates was investigated by differential scanning calorimetry and polarizing optical microscopy. The investigated compounds exhibit columnar mesophases. The formation of columnar superstructures was demonstrated for the sodium sulfonates by scanning force microscopy, gelation experiments, and proton magnetic resonance spectroscopy.</div>
<div type="abstract" xml:lang="en">Wedge‐shaped sulfonate amphiphiles self‐assemble in bulk and from solution to give rodlike structures with circular cross‐sections (see picture); this causes the formation of columnar mesophases, as well as gelation of the solution. Phase diagram investigations demonstrate that the transition from the gel state to the highly ordered bulk phase occurs through a lyotropic mesophase.</div>
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