Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

Abstract

SummaryLow molecular weight gelators are an important class of molecules. The supramolecular gels formed by carbohydrate derived low molecular weight gelators are interesting soft materials that show great potential for many applications. Previously, we have synthesized a series of methyl 4,6-O-benzylidene-α-D-glucopyranoside derivatives and found that several of them are good gelators for water, aqueous mixtures of DMSO, or aqueous mixtures of ethanol. The gelation efficiency of these glycolipid derivatives is dependent upon the structures of their acyl chains. In order to understand the influence of the anomeric position of the sugar headgroup towards self-assembly, we synthesized a series of 1-deoxyglucose analogs, and examined their gelation properties in several solvents. Several long chain esters, including diacetylene containing esters, and aryl esters exhibited gelation in ethanol, aqueous ethanol, or aqueous DMSO. The synthesis and characterization of these novel analogs are reported.

Configuration‐Controlled Crystal and/or Gel Formation of Protected d‐Glucosamines Supported by Promiscuous Interaction Surfaces and a Conformationally Heterogeneous Solution State

“…Moreover,i nt he case of 2,a sH 1, H3, and H5 all point in the same direction, the sugar ring of the b-anomer is also enabled for CH-p interactions.T he CH-p interaction between the sugar ring and the Fmocg roup of its neighborw as shown to be crucial in the assembly of the gel structure of av ery similar system,t hat of 2-deoxy-2-(9-fluorenylmethoxycarbonylamino)a-d-glucopyranose. [18] Our resultsp oint to ad ifferent conclusion concerning the fully protected variants of the same mole-cule. CH-p,m ore precisely polar-p,i nteraction is pivotal in the buildup of the crystal structures of both 1 and 2 and most probablyi nt he gels of 2,w hich were shown to provide seeds for crystallization.…”

“…Several free -OH containing or partially protected monoand oligosaccharides as well as the fully unprotected N-Fmoca,b-d-glucosamine have been shownt of orm hydrogels. [2,[17][18][19][20][21] An ovel class of supramolecular hydrogelsw as thus established, wheret he self-association of hydrophobic( aromatic) and hydrophilic (free -OH) molecularf ragments make up the amphiphilic system in which CH-p interactions were proposed to take over the role of more conventional p-p stacking and hydrogen-bond driven associations. [17] High-resolution NMR and X-ray crystallographic data wouldhave been needed, however,t oe laborate this promisingc oncept further.…”

Effect of the self-assembled gel network formed from a low molecular mass organogelator on the electron kinetics in quasi-solid-state dye-sensitized solar cells

“…Therefore, quasi-solid-state electrolytes which can be prepared by solidifying the liquid electrolytes using low molecular mass organogelators (LMOGs) [15,16], polymer gelators [17,18] and nanoparticles [19,20], have attracted much attention for their good properties (e.g., good performance and long stability). Remarkably, the gel electrolytes formed from the LMOGs exhibit three dimensional networks and possess higher ionic conductivity, good pore filling and penetration of the mesoporous TiO2 film [21,22]. Importantly, the devices assembled by LMOGs exhibit good long-term stability because of a high gel to solution transition temperature of LMOGs [23,24].…”

Quasi-solid-state dye-sensitized solar cell based on gel electrolyte with high gel to solution transition temperature using low molecular mass organogelator

“…Therefore, quasi-solid-state electrolytes have attracted much attention for their good performance and stability which can be prepared by solidifying the liquid electrolytes using low molecular mass organogelators (LMOGs) [19,20], polymer gelators [21,22] or nanoparticles [23,24]. Compared with the two kinds of electrolyte, the gel electrolytes formed from the LMOGs exhibit three dimensional networks and possess higher ionic conductivity, good pore filling and penetration of the mesoporous TiO 2 film [25,26].…”