(R)‐12‐Hydroxystearic Acid Hydrazides as Very Efficient Gelators: Diffusion, Partial Thixotropy, and Self‐Healing in Self‐Standing Gels,Chemistry - An Asian Journal

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(R)‐12‐Hydroxystearic Acid Hydrazides as Very Efficient Gelators: Diffusion, Partial Thixotropy, and Self‐Healing in Self‐Standing Gels
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2016-10-27 , DOI: 10.1002/asia.201601163
Jingjing Li _{1,

2} , Mohan Zhang ₂ , Richard G. Weiss _{2,

3}

Affiliation

The gelation properties of derivatives of N‐alkylated (R)‐12‐hydroxystearic acid hydrazide (n‐HSAH, n=0, 2, 6, 10; n is the length of an n‐alkyl chain on the terminal nitrogen atom) in a wide variety of liquids is reported. The n‐HSAH compounds were derived from a naturally occurring alkanoic acid, (R)‐12‐hydroxystearic acid (R‐12HSA), and although they differ from the analogous N‐alkyl (R)‐12‐hydroxystearamides (n‐HSAA) only by the presence of one N−H group, their behavior as gelators is very different. For example, the parent molecule (0‐HSAH) is a supergelator in ethylene glycol, in which it forms self‐standing gels that are self‐healing, partially thixotropic, moldable, and load‐bearing; gels of 0‐HSAA are not self‐standing. 0‐HSAH is structurally the simplest molecular gelator of which we are aware that is capable of forming both self‐standing and partially thixotropic gels. Also, diffusion of the cationic dye erythrosine B and the anionic dye methylene blue in 0‐HSAH/ethylene glycol gel blocks is much slower than the self‐diffusion of ethylene glycol. Polarizing optical microscopy, X‐ray diffraction, and FTIR studies revealed that the self‐assembled fibrillar networks (SAFINs) of the gels are crystalline, and that 0‐HSAH molecules may be arranged in a triclinic subcell with bilayer stacking. The SAFINs are stabilized by strong hydrogen‐bonding interactions between the hydrazide groups of adjacent molecules and a perpendicular hydrogen‐bonding network between the pendent hydroxyl groups of 0‐HSAH. The other n‐HSAH (n=2, 6, 10) molecules appear to be arranged in orthorhombic subcells with monolayers and strong hydrogen‐bonding interactions between the hydrazide group of one gelator molecule and the hydroxyl group of a neighboring one. These results show how small structural modifications of structurally simple gelator molecules can be exploited to form gels with novel properties that can lead potentially to valuable applications, such as in drug delivery.

中文翻译：

（R）-12-羟基硬脂酰肼作为高效凝胶剂：扩散，部分触变性和自固定凝胶的自我修复

N-烷基化的（R）-12-羟基硬脂酸酰肼衍生物（n- HSAH，n = 0，2，6，10 ; n是末端氮原子上的n-烷基链的长度）的胶凝特性据报道有各种各样的液体。所述Ñ -HSAH化合物从天然存在的链烷酸，（派生- [R）-12-羟基硬脂酸（ř -12HSA），尽管它们从类似的不同N-烷基（[R）-12- hydroxystearamides（Ñ‐HSAA）仅存在一个N-H基团，它们作为胶凝剂的行为就大不相同。例如，母体分子（0-HSAH）是乙二醇的超级胶凝剂，它在其中形成可自我修复，部分触变，可塑和承重的自立式凝胶。0-HSAA凝胶不是自立的。0-HSAH是结构上最简单的分子胶凝剂，我们知道它能够形成自立和部分触变凝胶。而且，阳离子染料赤藓红B和阴离子染料亚甲基蓝在0-HSAH /乙二醇凝胶嵌段中的扩散比乙二醇的自扩散慢得多。偏光光学显微镜，X射线衍射和FTIR研究表明，凝胶的自组装原纤维网络（SAFIN）是结晶的，并且0-HSAH分子可以双层堆叠的方式排列在三斜亚细胞中。SAFIN通过相邻分子的酰肼基团之间的强氢键相互作用以及0-HSAH的侧链羟基之间的垂直氢键网络来稳定。另一个n -HSAH（n = 2、6、10 ）分子似乎排列在具有单层的正交晶系亚细胞中，一个胶凝剂分子的酰肼基团与相邻一个胶凝剂分子的羟基之间存在很强的氢键相互作用。这些结果表明如何利用结构简单的胶凝剂分子的微小结构修饰来形成具有新颖特性的凝胶，这些特性可能潜在地导致有价值的应用，例如在药物输送中。

更新日期：2016-10-27

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