In this study, we describe the synthesis and molecular properties of anthranilamide-based short peptides which were synthesised via ring opening of isatoic anhydride in excellent yields. These short peptides were incorporated as low molecular weight gelators (LMWG), bola amphiphile, and C3-symmetric molecules to form hydrogels in low concentrations (0.07–0.30% (w/v)). The critical gel concentration (CGC), viscoelastic properties, secondary structure, and fibre morphology of these short peptides were influenced by the aromaticity of the capping group or by the presence of electronegative substituent (namely fluoro) and hydrophobic substituent (such as methyl) in the short peptides. In addition, the hydrogels showed antibacterial activity against S. aureus 38 and moderate toxicity against HEK cells in vitro.

Precise control of tape spacing in hydrogen-bonded alkyl-chain substituted chloro-s-triazines is demonstrated at 150–298 K, with some unexpected behaviour from the odd-number carbon derivatives.

Crystalline bis‐N‐alkyl‐chlorotriazines 2–6 can be considered multilayers of lipid bilayers comprising a rigid hydrogen‐bonded tape in the polar layer separated by a lipid region of small to medium‐length alkyl chains. The persistent ordering of these tapes acts as a scaffold in the solid state enabling measurement of temperature‐induced conformational changes in the “lipid phase” using X‐ray crystallography. The alkyl chains in these structures are loosely packed but generally ordered at low temperature, undergoing a slow transition to a disordered structure clearly observed in the Raman spectrum. The longer‐chain derivatives 4–6 show a distinct Raman spectrum for the ordered and disordered crystallographic phases enabling a least squares fitting at each temperature point. Calibration of the Raman fit values for 5 and 6 using powder X‐ray diffraction allows a quantification of each phase and highlights the unique response of each derivative with temperature. This approach for quantifying the onset of disorder and structural phase transitions should be relevant to a wide range of lipid‐based systems.

First example of glyoxylamide-based short peptides which can encapsulate organic solvents and water at relatively low concentrations.

In this study, we prepared antibacterial hydrogels through the self-assembly of naphthyl anthranilamide (NaA) capped amino acid based cationic peptide mimics. These ultra-short cationic peptide mimics were rationally designed with NaA as a capping group, l-phenylalanine, a short aliphatic linker, and a cationic group. The synthesized peptide mimics efficiently formed hydrogels with minimum gel concentrations between 0.1 and 0.3%w/v. The resulting hydrogels exhibited desirable viscoelastic properties which can be tuned by varying the cationic group, electronegative substituent, or counter anion. Importantly, nanofibers from the NaA-capped cationic hydrogels were found to be the source of hydrogels’ potent bacteriacidal actvity against both Gram-positive and Gram-negative bacteria while remaining non-cytotoxic. These intrinsically antibacterial hydrogels are ideal candidates for further development in applications where bacterial contamination is problematic.