分子博罗姆环的选择性合成:通过协调驱动的自组装进行超分子拓工程
Taegeun Kim1, Nem Singh1, Jihun Oh1
1Department of Chemistry, University of Ulsan , Ulsan 44610, Republic of Korea.
Journal of the American Chemical Society
|June 24, 2016
概括
研究人员使用无模板方法合成了分子波罗密环 (BRs),这是化学中罕见的拓. 这一突破使得通过协调驱动的自我组装能够产生复杂的相互关联的分子.
科学领域:
- 超分子化学
- 化学合成
- 材料科学
背景情况:
- 分子波罗密环 (BRs) 代表了相互锁定的分子领域内的罕见和复杂的拓.
- 了解和合成这些复杂的分子结构对于推进超分子化学至关重要.
研究的目的:
- 报告一个新的无模板合成分子波罗密环 (BRs).
- 研究这些独特的分子拓的自我组装过程和结构特征.
主要方法:
- 采用基于四的 (II) 接受器和二氧化捐赠器的协调驱动自组装.
- 通过核磁共振 (NMR) 光谱和单晶X射线衍射 (XRD) 分析进行表征.
- 密度函数理论 (DFT) 计算研究以支持实验发现.
主要成果:
- 成功合成无模板的分子波罗密环 (BR).
- 在单体矩形和BR之间观察可逆转换.
- 晶体结构分析显示,该拓是由金属循环几何和pi-pi相互作用决定的.
- 计算研究证实了分散性分子间相互作用在BR形成中的作用.
结论:
- 这项研究提出了一种有效的方法来合成无模板的分子波罗密环.
- 这些发现突显了特定分子几何和非共价相互作用在指导复杂的拓自组合中的重要性.
- 这项工作为设计和创建新的相互关联的分子架构提供了基础.
相关概念视频
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
6.4K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
6.4K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
3.3K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
3.3K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
21.8K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
21.8K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
7.8K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
7.8K
Regioselectivity and Stereochemistry of Hydroboration
9.7K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.7K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
5.3K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
5.3K


