Self-assembly of novel Fmoc-cardanol compounds into hydrogels – analysis based on rheological, structural and thermal properties

Abstract

Fluorenylmethyloxycarbonyl substituted cardanol derivatives self-assembled into long fibers in methanol and crosslinked to form gels in DMSO/water. The role of hydrogen-bonding, hydrophobicity, and π–π stacking in governing self-assembly and hydrogel formation is investigated.

Tumor Microenvironment Responsive “Head-to-Foot” Self-Assembly Nanoplatform for Positron Emission Tomography Imaging in Living Subjects

“…This might be attributed to the presence of the Fmoc group in 1a, which could enhance the intermolecular π−π stacking interaction. 49 However, as for the other control probe 1b, formation of nanoparticles cannot be observed since it cannot form dimers due to the absence of disulfide bond (Figure S49B). In order to prove which kind of CBT-Cys click ligation was the most prevalent for the probe 1 in living body, three possible reactions through which the CBT-Cys condensation may occur were investigated from the perspective of theoretical simulation.…”

“…After TCEP treatment and pH adjustment, 1a was found to be aggregated into nanoparticles ( 1a-NP ) of superior diameter than the nanoparticles 1-NP (400 nm vs 138 nm, Figure S49A), suggesting that the control probe 1a was more prone to self-assembly than the probe 1 . This might be attributed to the presence of the Fmoc group in 1a , which could enhance the intermolecular π–π stacking interaction . However, as for the other control probe 1b , formation of nanoparticles cannot be observed since it cannot form dimers due to the absence of disulfide bond (Figure S49B).…”

Mechanical Properties of Low-Molecular-Weight Peptide Hydrogels Improved by Thiol-Ene Click Chemistry

“…However, as the pH increased, the loose fibers in the aqueous solution entangled and aggregated with each other, forming nanofibrous rods in the FFCKK/MBA-8.0 sample (Figure 1e), which is in accordance with the structure in literature. 39,40 The internal structure of the samples changed from soft and bendable fibers to nanofiber rods, and the stacking between these nanofiber rods improved the mechanical properties of the hydrogels, suggesting that the samples were affected by the thiol-ene click chemistry. Therefore, we conclude that the addition of MBA can effectively improve the mechanical properties of the samples.…”

A novel tetrathiafulvalene based liquid crystalline organogelator: synthesis, self-assembly properties and potential utilization

“…LMOGs display unique liquid crystalline properties, which are potential candidates for developing optical electronics. [21][22][23][24][25][26][27][28][29] However, low-molecularweight compounds having both gelation ability and displaying thermotropic mesomorphic behavior at the same time remain relatively rare. It is serendipitous to obtain low-molecular-weight compounds capable of gelling solvents and exhibiting thermotropic mesomorphic behavior.…”