Self‐Assembly of Amphiphilic Calix[4]arenes in Aqueous Solution

Abstract

The self‐assembly of amphiphilic calix[4]arenes with either a carboxylic acid or a trimethyl ammonium head group and different alkyl chains in aqueous solution was investigated. The carboxylated calixarene forms vesicles in dilute solution and stable monolayers on water. In contrast, the ammonium head group provides high water solubility with no observed aggregation. At high concentrations, all calixarene amphiphiles form lyotropic liquid crystals.

Encapsulation of Drug Molecules into Calix[n]arene Nanobaskets. Role of Aminocalix[n]arenes in Biopharmaceutical Field

“…Thus, quaternary ammonium compounds demonstrate extremely high solubility, for example, compound 45 , and tend to form liquid crystals at higher concentrations rather than precipitate out. A good example of this phenomenon is shown with 47 and 48 , which form micelles in water that arrange to form a rectangular lattice in 50%–80% (w/v) concentration range . However, steric hindrance to hydration may cancel the advantages conferred by charge: cationic guanidine‐substituted CAs 28 , 30 , and 31 are relatively poorly water soluble (0.83%, 0.86%, and 0.57%, w/v, respectively), presumably because of hindered access of water molecules to the charge that is hidden inside the branched hydrophilic fragment .…”

Solution behavior of mixed systems based on novel amphiphilic cyclophanes and Triton X100: Aggregation, cloud point phenomenon and cloud point extraction of lanthanide ions

“…The synthesis of diverse amphiphilic molecules on the basis of calix [4]arene platform results in the development of new type of amphiphiles, which can be regarded as the intermediate point between conventional surfactants and some of biological compounds. The specific aggregation mode of cyclophane based amphiphiles is quite different from that of conventional surfactants, which is highlighted in literature [18][19][20][21]. Our previous work [22] elucidates the unusual ''headto-tail" self-aggregation mode for watersoluble amphiphilic calix [4]resorcinarene with sulfonatomethyl groups on the upper rim (head) and pentyl radicals (tails) on the lower rim.…”

“…The hydrophilic and hydrophobic contributions are less strongly marked in this case, indicating that the open model of the aggregation is more suitable. Though the peculiarities of the self-aggregation mode for various watersoluble calixarenes are widely represented in literature [18][19][20][21][22][23][24], the relationship between the aggregation mode and colloidal properties, such as cloud point behavior is not properly established.…”

Polycationic Macrocyclic Scaffolds as Potential Non-Viral Vectors of DNA: A Multidisciplinary Study

“…The zwitterionic lipid 1,2-dioleoyl-sn-glycero-3-phosphatidylethanolamine (DOPE) was purchased from Avanti Polar Lipids and has no charge at a physiological pH of 7.4. The polycationic calixarene-based lipidic vector CxCL is 5,11,17,23-tetrakis(trimethylammonio)-25,26,27,28-tetra-n-decyloxy calix [4]arene tetrachloride, referred to in this work as TMAC4; it was synthesized as described in the literature, 45 although the step for the chloromethylation was performed using a slightly modified literature procedure. 46 N(CH 3 ) 3 ), 1.88 (m,8H, -CH 2 -CH 2 -O-Ar), 1.32 (m, 56H, alkyl-CH 2 ), 0.85 (t, 12H, CH 3 -CH 2 -).…”