2877-29-4Relevant articles and documents
Design of dialkyl surfactants from nitrilotriacetic acid as head group
Trillo, Juan V.,Meijide, Francisco,Tato, Jose Vazquez,Jover, Aida,Soto, Victor H.,De Frutos, Santiago,Galantini, Luciano
, p. 6869 - 6877 (2014)
New double-chain surfactants can be designed in which nitrilotriacetic acid plays the role of glycerol in phospholipids. The synthetic methodology is applied to the synthesis of (2-(bis(2-dodecylamino)-2-oxoethyl)amino)acetic acid. This is a symmetric dimeric surfactant but the methodology allows the synthesis of asymmetric double-chain surfactants as well. The Krafft temperature is 16-18 °C. The critical aggregation concentration of the new surfactant (4.76 × 10-5 mol dm-3 in NaOH 0.01 M and 25 °C; surface tension measurements) is two hundred times lower than that for sodium 2-dodecanamidoacetate, which can be considered its monoalkyl surfactant analog, indicating the enhanced surfactant properties resulting from the presence of two hydrophobic alkyl chains. The shape of the aggregates was investigated by transmission electron microscopy. At 40 °C, the main structure present in solution corresponds to vesicles and, from the size distribution of their radii, values of (0.34 ± 0.06)kT and 56.7 ± 2.6 nm were obtained for the effective bending elasticity constant and the spontaneous radius of curvature of vesicles, respectively. The Royal Society of Chemistry 2014.
Chemical and constitutional influences in the self-assembly of functional supramolecular hydrogen-bonded nanoscopic fibres
Puigmarti-Luis, Josep,Minoia, Andrea,Perez Del Pino, Angel,Ujaque, Gregori,Rovira, Concepcio,Lledos, Agusti,Lazzaroni, Roberto,Amabilino, David B.
, p. 9161 - 9175 (2006)
A new series of secondary amides bearing long alkyl chains with π-electron-donor cores has been synthesized and characterised, and their self-assembly upon casting at surfaces has been studied. The different supramolecular assemblies of the materials have been visualized by using atomic force microscopy (AFM) and transmission electron microscopy (TEM). It is possible to obtain well-defined fibres of these aromatic core molecules as a result of the hydrogen bonds between the amide groups. Indeed, by altering the alkyl-chain lengths, constitutions, concentrations and solvent, it is possible to form different rodlike aggregates on graphite. Aggregate sizes with a lower limit of 6-8 nm width have been reached for different amide derivatives, while others show larger aggregates with rodlike morphologies which are several micrometers in length. For one compound that forms nanofibres, doping was 'performed by using a chemical oxidant, and the resulting layer on graphite was shown to exhibit metallic-like spectroscopy curves when probed with current-sensing AFM. This technique also revealed current maps of the surface of the molecular material. Fibre formation not only takes place on the graphite surface: nanometre scale rods have been imaged by using TEM on a grid after evaporation of solutions of the compounds in chloroform. Molecular modelling proves the importance of the hydrogen bonds in the generation of the fibres, and indicates that the constitution of the molecules is vital for the formation of the desired columnar stacks, results that are consistent with the images obtained by microscopic techniques. The results show the power of noncovalent bonds in self-assembly processes that can lead to electrically conducting nanoscale supramolecular wires.
Diversity oriented synthesis of novel haloglycolipids potentially useful for crystallization of integral membrane proteins
Sahoo, Laxminarayan,Singhamahapatra, Anadi,Loganathan, Duraikkannu
, p. 2615 - 2625 (2014/04/17)
A series of novel haloglycolipids were synthesized based on Cu(i) catalyzed Huisgen's [3 + 2] cycloaddition reaction of diversely functionalized azides and alkynes, using a mixture of N-bromosuccinimide and Cu(i) halide as the halogen source. Since halogen atoms, like bromine and iodine, with a very high scattering power facilitate the solving of crystal structures, the title haloglycolipids could prove to be invaluable in structure-based drug design involving membrane proteins as targets. This journal is the Partner Organisations 2014.
