A novel nanostructured supramolecular hydrogel self-assembled from tetraphenylethylene-capped dipeptides

Abstract

Herein, we report a tetraphenylethylene-diglycine (TPE-GG) hydrogelator from a systematic study of TPE-capped dipeptides with various amphiphilic properties. From a chemical design, we found that the hydrogelation of TPE-GG molecules can be utilized to generate supramolecular nanostructures with a large TPE-based nanobelt width (∼300 nm) and lateral dimension ratio (>30 fold). In addition, TPE-GG has the lowest molecular weight and minimum number of atoms compared to any TPE-capped peptide hydrogelator reported to date. This minimal self-assembled hydrogelator can fundamentally achieve the gel features compared with other TPE-capped peptides. A combined experimental and computational study indicates the π-π interactions, electrostatic interactions and hydrogen-bonding interactions are the major driving forces behind the formation of self-assembled nanobelts. This study demonstrates the importance of structure-property relationships and provides new insights into the design of supramolecular nanomaterials.

Aggregation‐Induced Emission for Visualization in Materials Science

“…[50] Significantly,o ther measurements testifying to the gelation evolution have been investigated, such as transmittance, circular dichroism spectra, and mechanical properties (storage modulus, compression stress, and shrinkage rate). [51] These measurements provided evidence for the accuracy of the fluorescent visualizations. Therefore, the proposed visualizations trategy provided insights for the mechanistic understanding and the rational design of hydrogels for various applications.…”

“…Significantly, other measurements testifying to the gelation evolution have been investigated, such as transmittance, circular dichroism spectra, and mechanical properties (storage modulus, compression stress, and shrinkage rate) . These measurements provided evidence for the accuracy of the fluorescent visualizations.…”

Synthesis and Properties of New Alkyl Alanine Dipeptides Based on Difluoroboron β‐diketonates

“…Synthesis of C 10 H 21 CO‐Ala‐Ala‐OH ( 3 ). All four dipeptides 3 were synthesized following the manual solid phase peptide synthesis (SPPS) procedure, which was similar to those already reported in the literature , …”

“…However, as far as we know, little has been studied for dipeptides derivatives with organoboron chromophores up to now . The introduction of various chiral dipeptide units may provide diverse chirality, and develop supramolecular hydro/organo‐gelators for practical use …”

An Efficient Approach for the Synthesis of 1,2,3‐Triazole Moiety to Generate Uracil Molecular Architectures Through Cu‐Catalyzed Azide–Alkyne Cycloaddition

“…Efforts have been focused on the development of supramolecular materials featuring biological units by the chemical combination of biological molecules such as nucleic acids, amino acids, peptides, or sugar with lipids, which remains an amazing approach to create new hybrid amphiphilic structures. Because of their potential biomedical applications as low molecular weight gelators, amphiphiles combining sugar, nucleic acid, and lipid moieties, namely, glycosyl‐nucleoside lipids, have emerged as biocompatible materials of particular interest due to their intrinsic properties, in particular, the non‐covalent nature of the molecular interactions at work (π–π stacking between the nucleobases and/or the triazole moieties, intermolecular hydrogen bond, etc.) .…”