Wedge-shaped molecules with a sulfonate group at the tip--a new class of self-assembling amphiphiles.
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.
Zhu
Xiaomin
X
Institut für Technische Chemie und Makromolekulare Chemie, Lehrstuhl für Textilchemie und Makromolekulare Chemie der RWTH Aachen, Worringerweg 1, 52056 Aachen, Germany.
Tartsch
Bernd
B
Beginn
Uwe
U
Möller
Martin
M
D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry; D005782:Gels / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D018625:Microscopy, Atomic Force; D015394:Molecular Structure; D011522:Protons; D013451:Sulfonic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013501:Surface-Active Agents / Q000737:chemistry*
C504576:4-N-(3',4',5'-tris(dodecyloxy)benzamido)benzene-4-sulfonic acid; D001391:Azo Compounds; D001549:Benzamides; D005782:Gels; D011522:Protons; D013451:Sulfonic Acids; D013501:Surface-Active Agents