106-14-9Relevant articles and documents
Chirality-controlled syntheses of double-helical Au nanowires
Nakagawa, Makoto,Kawai, Takeshi
, p. 4991 - 4994 (2018)
The selective large-scale syntheses of noble metal nanocrystals with complex shapes using wet-chemical approaches remain exciting challenges. Here we report the chirality-controllable syntheses of double-helical Au nanowires (NWs) using chiral soft-templates composed of two organogelators with their own active functions; one organogelator serves to introduce helicity into the template and the other acts as a capping agent to control the Au shape. One-dimensional twisted-nanoribbon templates are prepared simply by mixing the two organogelators in water containing a small amount of toluene, followed by the addition of LiCl; template chirality is controlled through the selection of the handedness of the helicity-inducing organogelator. Double-helical Au NWs synthesized on these chiral templates have the same helical structure as the template because the Au NWs grow along both edges of the twisted nanoribbons with right- or left-handed helicities. Dispersions of the right- and left-handed double-helical Au NWs exhibit opposite CD signals.
Influence of chirality on the modes of self-assembly of 12-hydroxystearic acid in molecular gels of mineral oil
Grahame, Douglas A. S.,Olauson, Caitlin,Lam, Ricky S. H.,Pedersen, Tor,Borondics, Ferenc,Abraham, Shibu,Weiss, Richard G.,Rogers, Michael A.
, p. 7359 - 7365 (2011)
The gelating abilities of enantiopure, racemic, and different enantio-enriched mixtures of 12-hydroxystearic acid (12HSA) have been compared in order to clarify conflicting reports in the literature (1) concerning their ability to gelate organic liquids. Less than 1.0 wt % of optically pure (D)-12HSA was found to gelate mineral oil. The gel matrix was comprised of high aspect ratio fibers in which the 12HSA molecules were organized as head-to-head dimers and the 12-hydroxyl groups formed an H-bonding network along the axis transverse to the longitudinal growth. Below 2 wt %, racemic 12HSA in mineral oil did not reach the percolation threshold. Its organogels were comprised of platelet-like crystals with a molecular arrangement of single, in-plane, hydrogen-bonded acyclic dimers that prevent longitudinal growth and limit the ability of the polar groups to phase separate during nucleation.
Cyclic fatty acyl glycosides in the glandular trichome exudate of Silene gallica
Asai, Teigo,Fujimoto, Yoshinori
, p. 1410 - 1417 (2010)
Chemical investigation of the glandular trichome exudate from Silene gallica L. (Caryophyllaceae) resulted in isolation of 10 cyclic fatty acyl glycosides (gallicasides A-J). The cyclic structures were characterized by a glycosidic linkage of the glucose moiety to either the C-12 or the C-13 position of the octadecanoyl moiety, and by an ester linkage between the C-2 hydroxy group of the glucose moiety and the carboxyl group of the oxygenated octadecanoic acid. The structures of the cyclic fatty acyl glycosides were further distinguished from one another by acetylation and/or malonylation on the glucose moiety. Of these compounds, the 1,2′-cyclic ester of 12(R)-(6-O-acetyl-3-O-malonyl-β-d-glucopyranosyloxy)octadecanoic acid (gallicaside J) was the most abundant (30.7%). These secondary metabolites were found specifically in the glandular trichome exudate rather than in other aerial parts.
A General Approach to Intermolecular Olefin Hydroacylation through Light-Induced HAT Initiation: An Efficient Synthesis of Long-Chain Aliphatic Ketones and Functionalized Fatty Acids
Guin, Joyram,Paul, Subhasis
, p. 4412 - 4419 (2021/02/05)
Herein, an operationally simple, environmentally benign and effective method for intermolecular radical hydroacylation of unactivated substrates by employing photo-induced hydrogen atom transfer (HAT) initiation is described. The use of commercially available and inexpensive photoinitiators (Ph2CO and NHPI) makes the process attractive. The olefin hydroacylation protocol applies to a wide array of substrates bearing numerous functional groups and many complex structural units. The reaction proves to be scalable (up to 5 g). Different functionalized fatty acids, petrochemicals and naturally occurring alkanes can be synthesized with this protocol. A radical chain mechanism is implicated in the process.
