Wedge‐Shaped Molecules with a Sulfonate Group at the Tip—A New Class of Self‐Assembling Amphiphiles

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.

Thin Film Morphologies of Block Copolymers Complexed with Wedge-Shaped Liquid Crystalline Amphiphilic Molecules

“…26,27 In the present work, the synthesis of a wedge-shaped amphiphilic sulfonic acid molecule with three octyl substituents is described, which is linked to poly(2-vinylpyrydine)-blockpoly(ethylene oxide) (P2VP-b-PEO) copolymer via an acid base interaction. Three complexes with different degrees of neutralization of the P2VP block have been prepared and analyzed by Fourier transform infrared (FT-IR) and X-ray photoelectron spectroscopy (XPS).…”

Ionic Liquid Crystals Based on Pyridinium Salts

“…The protonated pyridinium cation was employed to generate liquid crystalline materials having as counterions a series of wedge-shaped benzenesulfonate mesogens 4-6 [7,8]. Compound 4, having a rather unusual substitution pattern, 2,3,4-tris(dodecyloxy)benzenesulfonate, exhibits a reversible transition from a columnar disordered phase into an ordered columnar during the slow heating and cooling cycles.…”

Self‐Assembly of a Low‐Symmetry Monodendron Containing Two Asymmetrically Linked Molecular Wedges

“…for example ref. [9]). It is likely that the compound crystallizes upon further cooling to 14 8C, since the enthalpy of this transition is rather high.…”

“…[4,5] Monodendrons can selfassemble into smectic or columnar phases with or without the formation of supramolecular discs, [5] which can be in turn stacked in columns stabilized by specific interactions, such as p-p interactions, [6] H-bonding, [7,8] or ionic interactions. [9] The arrangement of the bulky side groups can be sometimes improved by rotation of each layer in the column by a certain angle relative to the previous layer. As a result, regular helicoidal structures with a circular cross section are formed.…”