Studies on a novel class of triaryl pyridine N-glycosylamine amphiphiles as super gelators

Abstract

A novel class of six different triaryl pyridine N-glycosylamine amphiphiles was synthesised and characterized based on different spectral techniques, such as NMR and mass analysis. Gelation properties in different aromatic and aliphatic solvents were studied and gelation was observed predominantly in aliphatic solvents with CGC of 0.5% (w/v) and is attributed to the presence of long alkyl chain. All the gels thus obtained were studied using FE-SEM and powder XRD techniques which reveal fibrous entanglement of the molecules in the gel state with intermolecular spaces of 3.62 nm and 0.43 nm.

One-pot synthesis of fluorescein based β-aminoglycosylketones and their biological and material applications

“…Recently, we have reported the gelating abilities of different class of sugar derivatives, [17][18][19] and observed that uorescein based b-aminoglycosylketones are better candidate for the gel formation (CGC: 1%) in Table 1. All gel samples were prepared by dissolving the gelator in a solvent in such a way that it forms a homogenous solution.…”

“…[14][15][16] Moreover, the selfassembly of sugar based-amphiphilic systems is thus emerging as a particular powerful strategy to direct the self-assembly of relatively simple glycosylamines into sophisticated materials possessing wide applications. 17,18 In addition the gels can be stabilized by intermolecular hydrogen bonds between sugar-OH groups as well as van der Waals interactions between alkyl groups. In the search of new molecular entities with potential gelation ability, we have recently reported 4,6-O-protected-b-Cglycosides 19 as potential gelators with diverse applications.…”

Organogels Based on Natural Products

“…能形成有机凝胶的闭环糖衍生物大多是在糖分子中 引入能提供 π-π 作用力的芳香基团, 利用糖分子的羟基 形成的氢键作用力, 一般能够自组装成纳米纤维结构. 例如, 由 Das 等 [58] 合成的基于芳香环为核中心的 4, 6 位 被保护的 β 碳糖苷化合物 74～79, 在包括甲醇、氯仿、 苯类的有机溶剂中都能形成凝胶, 且溶液状态转变为凝 胶状态的同时, 组装形貌有球状转变成纤维结构. 刺激响应性凝胶是有机凝胶研究的热点, 最近, Das 等 [59] 将光构型转换基团偶氮苯引入到糖分子中, 合成 了 N-糖基偶氮苯化合物(N-glycosylazobenzene, GAZ), 该化合物能够在芳香烃溶剂中通过糖分子间氢键和反 式偶氮苯的 π-π 堆积作用形成稳定的凝胶, 而经紫外光 照射反式偶氮苯转变为顺式构型后扭曲的偶氮苯失去 π-π 作用力, 使凝胶坍塌, 实现了光刺激的凝胶溶胶的 转变(图 18).…”

Insights into a novel class of azobenzenes incorporating 4,6-O-protected sugars as photo-responsive organogelators

“…1 Representative examples of sugar-based low molecular weight organogelators reported in the literature. 1,13 azobenzene, 20 stilbene, 21 butadiene, 22 dithienylethene, 23 spiropyran, 24 and anthracene groups 25 are extensively incorporated to from photo-responsive materials. Similarly, the introduction of the p-methoxy group to the benzylidene acetal affects the gelation property.…”