Synthesis of Fan-Shaped C ₃ Molecule with Three Glycyrrhetinic Acid Units and Self-Assembly Properties

Abstract

A novel fan-shaped C 3 molecule with three glycyrrhetinic acid units was synthesized via "click chemistry" in high yield and the self-assembly characteristics were studied in different mixed solvents.

Supramolecular helical nanofibers assembled from a pyridinium-functionalized methyl glycyrrhetate amphiphile

“…21 Br-GA-CO 2 Me (546 mg, 0.90 mmol) was dissolved in 25 mL pyridine, and then stirred at room temperature for 10 h. After evaporating the solvent under reduced pressure, the crude product was purified by chromatography (CH 2 Cl 2 /CH 3 OH = 20:1 to 10: 21 Br-GA-CO 2 Me (546 mg, 0.90 mmol) was dissolved in 25 mL pyridine, and then stirred at room temperature for 10 h. After evaporating the solvent under reduced pressure, the crude product was purified by chromatography (CH 2 Cl 2 /CH 3 OH = 20:1 to 10: …”

Organogels Based on Natural Products

“…另外, 我们 [36] 合成了以三嗪为核骨架的含有 3 个甘 草次酸单元的 C 3 对称扇形分子 37, 该化合物在四氢呋 喃和甲醇的混合溶剂中(V∶V＝3∶1) 也能够表现出弱 的凝胶性质, 通过扫描电镜, 能清楚地观察到由纤维相 互缠绕成的直径约为 40～100 nm 的空腔(图 11).…”

Steroid/Triterpenoid Functional Molecules based on “Click Chemistry”

“…Synthesis of novel fan-shaped C 3 -symmetric molecule with three glycyrrhetinic acid units using CuAAC "click" chemistry. [44] [44] 2644 www.chemasianj.org was produced by the delocalization of H b after enough F À ions were added. In addition, it was demonstrated that the carbonyl groups, the stretching vibration bands of which appear at higher wavenumber, linked with CH b 2 , while another carbonyl group appears close to CH a 2 in the IR spectra.…”

“…[43] Using CuAAC "click" chemistry, a novel fan-shaped C 3 -symmetric molecule with three glycyrrhetinic acid units was synthesized by us (Scheme 5) and its self-assemble behavior was studied in different mixed solvents. [44] The results indicated that the fanshaped molecule 40 could form a weak organogel in tetrahydrofuran (THF)-methanol mixture with the MGC (MGC is the minimum gelator concentration at which gelation was observed to restrict the flow of the medium) of 2.3 g/100 cm 3 and the T gel = 36 8C. The scanning electron microscopy (SEM) images revealed that 40 could self-assemble into nanoscale fibrous structures with regular diameters of approximately 40-100 nm (Figure 16).…”

“…Owing to the high reactivity of chlorine atoms in cyanuric chloride (2,4,6‐trichloro [1,3,5]triazine) toward nucleophiles, it is generally used as the starting material for the preparation of different triazine derivatives, including dendrimers, in which the triazine ring acts as the constructive core 43. Using CuAAC “click” chemistry, a novel fan‐shaped C 3 ‐symmetric molecule with three glycyrrhetinic acid units was synthesized by us (Scheme ) and its self‐assemble behavior was studied in different mixed solvents 44. The results indicated that the fan‐shaped molecule 40 could form a weak organogel in tetrahydrofuran (THF)–methanol mixture with the MGC (MGC is the minimum gelator concentration at which gelation was observed to restrict the flow of the medium) of 2.3 g/100 cm 3 and the T gel =36 °C.…”