156447-53-9Relevant academic research and scientific papers
Investigation of mesomorphic, photophysical and gelation behavior in aroylhydrazone based liquid crystals: Observation of mesophase crossover phenomena
Kanth, Priyanka,Shankar Rao,Krishna Prasad,Singh, Bachcha
, (2021/08/06)
Five series of substituted aroylhydrazones having two alkoxy chains at 3- and 5- positions at amide end of the molecule have been synthesized; wherein each series differ from each other in terms of number and position of alkoxy chains at imine end. The compounds of first series with the single alkoxy chain at 4-position at imine end self-assembled into columnar hexagonal mesophase. The lower homologues of the series with alkoxy chains at 3- and 5- positions at imine end showed a transition from columnar hexagonal to columnar rectangular mesophase in cooling cycle while the higher homologues exhibited columnar hexagonal mesophase. The series with alkoxy chains at 3- and 4- positions exhibited columnar rectangular mesophase. All the homologues of series with alkoxy chains at 2-, 3- and 4- positions showed a transition from columnar rectangular to columnar oblique mesophase in cooling cycle. The series with alkoxy chains at 3-, 4- and 5- positions exhibited transition in columnar hexagonal mesophase. The mesophase crossover from one columnar mesophase to the other was found to be dependent on the chain length as well as on the temperature during the self-assembly process in these molecules. The temperature dependent columnar mesophase crossover has been observed for the first time in these systems. The substitution pattern showed an influence on the photophysical properties. The number and position of alkoxy chains played a critical role in the formation of gel in these molecules. These liquid crystalline gelators have application potential in organic optoelectronic functional materials and devices.
Targeted Delivery of mRNA with One-Component Ionizable Amphiphilic Janus Dendrimers
Zhang, Dapeng,Atochina-Vasserman, Elena N.,Maurya, Devendra S.,Liu, Matthew,Xiao, Qi,Lu, Juncheng,Lauri, George,Ona, Nathan,Reagan, Erin K.,Ni, Houping,Weissman, Drew,Percec, Virgil
, p. 17975 - 17982 (2021/11/10)
Targeted and efficient delivery of nucleic acids with viral and synthetic vectors is the key step of genetic nanomedicine. The four-component lipid nanoparticle synthetic delivery systems consisting of ionizable lipids, phospholipids, cholesterol, and a PEG-conjugated lipid, assembled by microfluidic or T-tube technology, have been extraordinarily successful for delivery of mRNA to provide Covid-19 vaccines. Recently, we reported a one-component multifunctional sequence-defined ionizable amphiphilic Janus dendrimer (IAJD) synthetic delivery system for mRNA relying on amphiphilic Janus dendrimers and glycodendrimers developed in our laboratory. Amphiphilic Janus dendrimers consist of functional hydrophilic dendrons conjugated to hydrophobic dendrons. Co-assembly of IAJDs with mRNA into dendrimersome nanoparticles (DNPs) occurs by simple injection in acetate buffer, rather than by microfluidic devices, and provides a very efficient system for delivery of mRNA to lung. Here we report the replacement of most of the hydrophilic fragment of the dendron from IAJDs, maintaining only its ionizable amine, while changing its interconnecting group to the hydrophobic dendron from amide to ester. The resulting IAJDs demonstrated that protonated ionizable amines play dual roles of hydrophilic fragment and binding ligand for mRNA, changing delivery from lung to spleen and/or liver. Replacing the interconnecting ester with the amide switched the delivery back to lung. Delivery predominantly to liver is favored by pairs of odd and even alkyl groups in the hydrophobic dendron. This simple structural change transformed the targeted delivery of mRNA mediated with IAJDs, from lung to liver and spleen, and expands the utility of DNPs from therapeutics to vaccines.
Tetrakis(Oxadiazolylphenyl)pyrazines: New st. Andrew’s cross-shaped liquid crystals
R?der, Nico,Marszalek, Tomasz,Limbach, Daniel,Pisula, Wojciech,Detert, Heiner
, p. 463 - 469 (2019/06/03)
π-Conjugated molecules with the shape of St. Andrew’s cross have been synthesized via fourfold Huisgen reaction. Four 2,5- diaryl-1,3,4-oxadiazol arms are attached to a central pyrazine nucleus. These fluorescent stars, when decorated with a rim of eight alkoxy side chains are discotic liquid crystals. Depending on the substitution pattern, the width of the liquid phase varies within a broad range of 25°C to 250°C. In their liquid crystalline phase, the molecules assemble in a typical hexagonal columnar supramolecular arrangement.
Supramolecular gelation of alcohol and water by synthetic amphiphilic gallic acid derivatives
Tamiaki, Hitoshi,Ogawa, Keishiro,Enomoto, Keisuke,Taki, Kazutaka,Hotta, Atsushi,Toma, Kazunori
supporting information; experimental part, p. 1661 - 1666 (2010/04/24)
The supramolecular organogelation of alcohols was observed in relatively hydrophobic amphiphiles with a short oligo(ethylene glycol) unit and three long alkyl chains at room temperature, while the hydrogelation occurred in more hydrophilic gelators with a longer poly(ethylene glycol) unit and two long alkyl chains at various temperatures. When a hot aqueous solution of some of the synthetic hydrogelators was cooled down, the supramolecular hydrogel was formed at room temperature. In some other amphiphiles with less intermolecular interactivity in water at room temperature, a reverse phase transition of sol to gel was observed by elevating the temperature of their aqueous systems, especially below a physiological temperature, 37 °C. The supramolecular hydrogelation at a low or high temperature was dependent on a slight molecular modification of the synthetic amphiphiles.
Facile synthesis of stable lipid analogues possessing a range of alkyl groups: Application to artificial glycolipids
Azefu, Yasuo,Tamiaki, Hitoshi,Sato, Reiko,Toma, Kazunori
, p. 4013 - 4022 (2007/10/03)
Efficient preparation of lipid analogues is described in which various long alkoxy chains and 2-hydroxyethyl group were covalently linked with benzoic acid derivatives. An α-mannopyranosyl group was stereoselectively introduced by the conventional imidate
Liquid-crystalline complexes of palladium(II) and platinum(II) with di- and tri-alkoxystilbazoles: Ligand control of mesomorphism
Donnio, Bertrand,Bruce, Duncan W.
, p. 2745 - 2755 (2007/10/03)
Liquid-crystalline complexes of palladium and platinum are formed when the metals are complexed to stilbazoles (4-styrylpyridines) bearing either two or three alkoxy chains. The complexes, termed polycatenar, show smectic C mesophases for most 3,4-disubstituted ligands, while the use of trisubstituted ligands leads to complexes showing columnar organisation, demonstrating that the spatial organisation of the metals in the liquid-crystal mesophase can be rather readily controlled. Complexes of these di- and tri-substituted stilbazoles with a cis-dicarbonylchloroiridium(I) fragment were not liquid crystalline.
