Two‐Component Supramolecular Gels Derived from Amphiphilic Shape‐Persistent Cyclo[6]aramides for Specific Recognition of Native Arginine

Abstract

A unique supramolecular two-component gelation system was constructed from amphiphilic shape-persistent cyclo[6]aramides and diethylammonium chloride (or triethylammonium chloride). This system has the ability to discriminate native arginine from 19 other amino acids in a specific fashion. Cyclo[6]aramides show preferential binding for the guanidinium residue over ammonium groups. This specificity was confirmed by both experimental results and theoretical simulations. These results demonstrated a new modular displacement strategy, exploring the use of species-binding hydrogen-bonded macrocyclic foldamers for the construction of two-component gelation systems for selective recognition of native amino acids by competitive host-guest interactions. This strategy may be amenable to developing a variety of functional two-component gelators for specific recognition of various targeted organic molecular species.

Enantioselective Recognition by Chiral Supramolecular Gels

“…Such phase changes can be gel-sol, sol-gel, gel-precipitation, and so on. Supramolecular gel formation and collapse have been used as am eans of the visual detection of ionic species and amino acid, [57][58][59][60][61] whereas there are only af ew cases in which chiral recognition has been realized. [62][63][64][65][66][67][68][69][70][71][72][73]…”

The Rich Tautomeric Behavior of Campestarenes

“…As the central part of ah ydrogen bond, ap roton is responsible for the conformation of oligoamide foldamers [1][2][3][4] ando ligohydrazide macrocycles, [5][6][7] and it can directt he formation of macrocyclic oligoamides [8][9][10][11] and Schiff bases. As the central part of ah ydrogen bond, ap roton is responsible for the conformation of oligoamide foldamers [1][2][3][4] ando ligohydrazide macrocycles, [5][6][7] and it can directt he formation of macrocyclic oligoamides [8][9][10][11] and Schiff bases.…”

Poly(aryl ether) Dendrons with Monopyrrolotetrathiafulvalene Unit‐Based Organogels exhibiting Gel‐Induced Enhanced Emission (GIEE)

“…The construction of functional materials through the bottom‐up approach associated with molecular self‐assembly allows the translation of information from the molecular scale into materials with specific functions 1. Over the last decade, supramolecular gels,2 representing one of the most important soft materials, have attracted widespread attention because of their potential applications in drug delivery,3 tissue engineering,4 sensors and actuators,5 template materials,6 removal of pollutants,7 enzyme immobilization matrices,8 catalysis,9 and crystal growth,10 using noncovalent interactions (hydrogen bonding, π–π interactions, metal–ligand coordination, van der Waals forces, London dispersion forces, donor–acceptor interactions and hydrophobic effects) for forming nanofibrillar structures able to “freeze” solvents in the rigid gel framework 11. Among them, low‐molecular mass organogelators (LMOGs) can be cross‐linked into different 3D self‐assembled blocks, such as fibers, rods, ribbons, or other morphologies, through noncovalent interactions.…”

“…[1] Over the last decade, supramolecular gels, [2] representing one of the mosti mportant soft materials, have attractedw idespread attentionb ecause of their potential applications in drug delivery, [3] tissue engineering, [4] sensors and actuators, [5] template materials, [6] removal of pollutants, [7] enzyme immobilization matrices, [8] catalysis, [9] and crystal growth, [10] using noncovalent interactions (hydrogen bonding, p-p interactions, metal-ligand coordination, van der Waals forces, London dispersion forces, donor-acceptori nteractions and hydrophobic effects) for formingn anofibrillar structuresa ble to "freeze" solvents in the rigid gel framework. [11] Among them, low-molecular mass organogelators (LMOGs) can be cross-linked into different 3D self-assembled blocks, such as fibers, rods, ribbons, or other morphologies, through noncovalent interactions. Because of the weak nature of these forces, the gel-solution( gel-sol) transition for organo-gels is thermally reversible and can be further tunedb yo ther physicaland chemical stimuli.…”