We report on the synthesis and self-assembly of a new series of twin-tapered dihydrazide derivatives, oxalyl acid N′, N′-di(3,4,5-trialkoxybenzoyl)-hydrazide (FH-Tn). Results from 1 H NMR diluting experiments in chloroform and temperature-dependent 1 H NMR spectroscopy revealed that molecules exhibited a conformational change at concentrations lower than 255 µM, e.g., from intramolecularly H-bonded sixmembered rings to five-membered rings in the monomer state upon concentrating. Measurements of 1 H NMR diluting experiment, FTIR spectroscopy, and mass spectroscopy revealed that the FH-Tn selfassembled into supramolecular chains either in chloroform at concentrations greater than 255 µM or in bulk through intermolecular quadruple H-bonding. On the basis of the results of DSC, polarized optical microscopy, and wide-angle X-ray diffraction (WAXD), we assigned enantiotropic hexagonal and unknown columnar phases to FH-Tn (n ) 6, 7, 8, 10).
We have demonstrated ultrasound-induced organogels based on twin-tapered dihydrazide derivatives, oxalyl acid N,N-di(3,4,5-trialkoxybenzoyl)hydrazide (FH-Tn). Ultrasound irradiation has been proved to influence gel properties at micro-levels. Different self-assembled structures from entangled fibers to tube-like structures and nanoparticles can be easily manipulated by tuning irradiation time and water bath temperature. FT-IR spectra exhibit weakened hydrogen bonding interactions, and XRD studies showed different packing modes before and after sonication. In addition, ultrasound can have effects on gel properties at macro-levels. Gels obtained from ultrasound treatment possess different wetting properties, relatively worse rheological properties and thermo-stability. Kinetic studies based on dynamic fluorescence spectra, rheological studies and theoretical calculations suggest that molecular aggregation mode differed from one-dimension to two-dimension for the gel after sonication.
An acylhydrazone-based colorimetric and fluorescent sensor (PAH-8) for the detection of F− and TFA/TEA has been studied. PAH-8 solution and organogel are highly selective and sensitive to F− among various tested anions in DMSO.
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