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Reactions of Folded Molecules in Water

水中折叠分子的反应

基本信息

批准号：
1801153
负责人：
Julius Rebek
金额：
$ 52万
依托单位：
The Scripps Research Institute
依托单位国家：
美国
项目类别：
Continuing Grant
财政年份：
2018
资助国家：
美国
起止时间：
2018-08-01 至 2020-09-30
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1801153&HistoricalAwards=false
关键词：
Reactions Folded Molecules Water

项目摘要

The majority of processes that take place in the chemical industry use organic solvents, solvents that are generally obtained from petrochemicals. Adapting these processes to the "greenest" solvent - water - remains a challenge. This project to be conducted by Professor Julius Rebek at The Scripps Research Institute uses synthetic, container-shape, molecules for reactions in water. The "containers" act as nanovessels that show robust stability and can be used and re-used over a wide range of conditions. A broader impact of this research is the benefit of developing sustainable chemistry. Another impact is the discovery of new molecules for use in water-proof coatings and nanomachines. Postdoctoral researchers benefit from learning how research projects translate from chemical discovery to applications in new materials.The chemistry of molecules confined to small containers - nanoscale compounds known as cavitands - is a relatively new undertaking. This research takes advantage of an early discovery that long-chain organic compounds assume unusual, folded shapes within the cavitand's space. The folded shapes, induced by hydrophobic forces, push the substrate's ends together and promote large-ring cyclization processes. The cavitands act as templates. Folding also blocks some sites on the chain and exposes others to reactions with agents in the aqueous medium. The blocking action promises new chemical pathways for remote carbon-hydrogen activation in functionalization reactions that typically lead to 5 or 6-membered ring sizes. Functional groups that are remote in extended molecules are brought into proximity when folded in cavitands. The functions no longer act independently and can affect each other's reactivity; showing the consequences of this "entanglement" is one of the basic science novelties expected from this research. The practical consequences may include synthetic methods for access to molecules that cannot be made by conventional means.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.

在化学工业中发生的大多数过程使用有机溶剂，这些溶剂通常从石化产品中获得。使这些工艺适应“最绿色”的溶剂--水--仍然是一个挑战。这个项目将由斯克里普斯研究所的朱利叶斯·雷贝克教授进行，使用合成的容器形状的分子在水中进行反应。“容器”作为纳米血管，显示出强大的稳定性，可以在广泛的条件下使用和重复使用。这项研究的更广泛影响是发展可持续化学的好处。另一个影响是发现了用于防水涂料和纳米机器的新分子。博士后研究人员可以从学习研究项目如何从化学发现转化为新材料的应用中获益。限制在小容器中的分子化学-纳米级化合物，称为空腔-是一项相对较新的工作。这项研究利用了一个早期发现，即长链有机化合物在空腔空间内呈现出不寻常的折叠形状。由疏水力诱导的折叠形状将底物的末端推到一起并促进大环环化过程。空腔作为模板。折叠还阻断了链上的一些位点，并使其他位点暴露于与水性介质中的试剂的反应。阻断作用为官能化反应中的远程碳氢活化提供了新的化学途径，通常导致5或6元环尺寸。在延伸分子中远离的官能团在折叠成空穴时被带到接近的位置。这些功能不再独立发挥作用，可以影响彼此的反应;显示这种“纠缠”的后果是这项研究所期望的基础科学创新之一。该奖项反映了NSF的法定使命，并通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。

项目成果

期刊论文数量（5）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

Radical Reactions in Cavitands Unveil the Effects of Affinity on Dynamic Supramolecular Systems

空化配体中的自由基反应揭示了亲和力对动态超分子系统的影响

DOI：
发表时间：
2020
期刊：
J. Am. Chem. Soc.
影响因子：
0
作者：
Manuel Petroselli;Venkatachalam Angamuthu;Faiz-Ur Rahman;Xinluo Zhao;Yang Yu;Julius Rebek Jr.
通讯作者：
Julius Rebek Jr.

Relative hydrophilicities of cis and trans formamides

顺式和反式甲酰胺的相对亲水性

DOI：
10.1073/pnas.1911331116
发表时间：
2019-10-01
期刊：
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
影响因子：
11.1
作者：
Li, Yong-Sheng;Escobar, Luis;Yu, Yang
通讯作者：
Yu, Yang

Recognition with metallo cavitands

Metallo Cavitands 识别

DOI：
10.1073/pnas.1909154116
发表时间：
2019-09-03
期刊：
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
影响因子：
11.1
作者：
Rahman, Faiz-Ur;Li, Yong-sheng;Yu, Yang
通讯作者：
Yu, Yang

Selective Macrocycle Formation in Cavitands

Cavitands 中的选择性大环形成