N-乙氨基酸胺基尿素:一种多功能状螺旋结构建筑块
Qian Wang1, Si-Yi Liu1, Yun-Bao Jiang1
1College of Chemistry and Chemical Engineering and the MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, Xiamen University, Xiamen 361005, China.
Accounts of chemical research
|September 13, 2025
概括
研究人员开发了新的N-氨基酸胺基尿酸,用于增强离子识别和超分子化学. 这些性构建块使得高效的宏循环化和自我组装成为双螺旋,推进功能性氨酸材料.
科学领域:
- 超分子化学 超分子化学
- 有机化学 有机化学
- 材料科学 材料科学 材料科学
背景情况:
- 尿素是重要的分子框架,具有显著的结能力,可用于阳离子识别,催化和治疗.
- 传统的氨酸阳离子受体设计通常依赖于电子吸收组,这可能导致基本阳离子的稳定性问题.
研究的目的:
- 开发先进的N-乙氨基酸胺基尿素平台,以增强超分子功能.
- 探索N-氨基酸氨基尿素构成,折叠和材料特性之间的关系.
- 调查离子识别,性转移和宏环化合成的新策略.
主要方法:
- 设计和合成含有电子捐赠胺基组的N-胺基尿酸,通过分子内电荷转移 (ICT) 增强离子结合亲和力.
- 利用分子异质和N-N键形状切换来动态调节性转移.
- 利用折叠β转结构的模板效应,以实现高效的宏循环化和基于宏循环的纳米孔的构建.
主要成果:
- 通过ICT使用N-amidothioureas实现了离子结合亲和度的数量级增强.
- 通过构造性切换证明了对分子内性转移的动态控制.
- 实现了高效的宏循环化合成和跨膜运输纳米孔的构建.
- 通过螺旋性传播报告了具有线性CD-ee依赖性的超分子双螺旋体的自我组装.
结论:
- N-乙氨基酸胺基尿素为高级超分子功能提供了多功能平台,包括离子识别和性转移.
- 开发的状螺旋构建块对于创建基于硫尿素的新型材料至关重要,在自发分辨率和跨膜传输方面具有应用.
- 这项工作显著推进了尿素化学领域及其在功能材料中的应用.
相关概念视频
Structure of Amines
3.2K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...
3.2K
Amines to Amides: Acylation of Amines
3.4K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.4K
Preparation of 1° Amines: Gabriel Synthesis
4.5K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
4.5K
Preparation of Amides
3.9K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.9K
Chirality at Nitrogen, Phosphorus, and Sulfur
6.8K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
6.8K
Acid Halides to Amides: Aminolysis
4.2K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
4.2K


