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手性 4,4(')-联苯硅纳米结构的制备中手性反转。

Handedness inversion in preparing chiral 4, 4(')-biphenylene-silica nanostructures.

机构信息

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China.

出版信息

Nanotechnology. 2011 Apr 1;22(13):135605. doi: 10.1088/0957-4484/22/13/135605. Epub 2011 Feb 22.

DOI:10.1088/0957-4484/22/13/135605
PMID:21343637
Abstract

An anionic gelator, D-C12ValC10COONa, derived from D-valine can cause physical gels in water and organic solvents. Helical 4,4(')-biphenylene-silica nanotubes and nanoribbons were prepared using it with 3-aminopropyltrimethoxysilane as a co-structure-directing agent and 4,4(')-bis(triethoxysilyl)-1,1(')-biphenyl (BTESB) as precursor. It was found that the handedness of the hybrid silica nanotubes/nanoribbons is sensitive to the pH value and the concentration of the reaction mixtures. However, handedness inversion was not found by changing the reaction temperature. Circular dichroism spectra of the 4,4(')-biphenylene-silica nanotubes indicated that the chirality of the organic self-assemblies were successfully transferred to the twist of the biphenylene rings through the co-structure-directing agent. The handedness of the 4,4(')-biphenylene rings was also tunable by changing the pH value and the concentration of the reaction mixtures. The FESEM images and CD spectra taken after different reaction times indicated that the handedness inversion occurred after adding BTESB.

摘要

一种源自 D-缬氨酸的阴离子凝胶剂 D-C12ValC10COONa 可以在水和有机溶剂中引起物理凝胶。使用它与 3-氨丙基三甲氧基硅烷作为共结构导向剂和 4,4(')-双(三乙氧基硅基)-1,1(')-联苯(BTESB)作为前体,制备了螺旋 4,4(')-联苯-硅纳米管和纳米带。发现混合硅纳米管/纳米带的手性对反应混合物的 pH 值和浓度敏感。然而,通过改变反应温度,并没有发现手性反转。4,4(')-联苯硅纳米管的圆二色性光谱表明,通过共结构导向剂,有机自组装的手性成功地传递到联苯环的扭曲中。通过改变反应混合物的 pH 值和浓度,也可以调节 4,4(')-联苯环的手性。不同反应时间后拍摄的 FESEM 图像和 CD 光谱表明,加入 BTESB 后会发生手性反转。

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