RUI: CAS: Quinone-Based Macrocyclic Systems for Supramolecular Applications

RUI：CAS：用于超分子应用的基于醌的大环系统

• 批准号: 2104447
• 负责人: Jay Wackerly
• 金额: $ 23.5万
• 依托单位: Central College of Iowa
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2021
• 资助国家: 美国
• 起止时间: 2021-09-01 至 2024-08-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=2104447&HistoricalAwards=false
• 关键词: RUI; CAS; Quinone; Based; Macrocyclic

With the support of the Macromolecular, Supramolecular and Nanochemistry Program in the Division of Chemistry, Dr. Jay W. Wackerly of Central College plans to design and synthesize a new class of "host" molecules with "catch-and-release" capabilities. The "host" molecule has a cavity into which a smaller "guest" molecule can fit. Two unique features of this new class of hosts are: 1) the modular framework that enables control of the size, shape and electronic properties of the host for selective binding of a specific guest target, and 2) the switchable electronic property that permits the binding of target to be turned on and off. The binding properties and the reversible capture and release of electron-rich guest molecules and negatively charged ions, such as halide and phosphate ions, will be investigated. The research aims to gain a deeper fundamental understanding of intermolecular interactions and provide insights to the design of molecular receptor for water purification and waste treatment. The project will provide research training opportunities to undergraduate students, including students of underrepresented groups. The results of research will be integrated into undergraduate laboratory course and scientific demonstrations in the middle and high school science classrooms to arouse students’ interest in science. One notable aspect of these supramolecular host macrocycles to be developed is that they can change their electronic state when subjected to a redox stimulus due to the presence of two parallel facing quinone rings. This class of structures was given the name "cambiarene" from the Latin word "cambiare" meaning "to change". This research will explore how the embedded quinone rings can be modulated to give rise to different structural, electronic, and binding properties. The upper-rim of the macrocycle, which contains the quinone rings, will be lengthened and shortened from the original form to investigate how different sized guests can be accommodated within the cavity and how strongly guests bind with special attention being paid to the contributions from anion-pi interactions. The lower-rim of the macrocycle will be modified to control the cavity size and the distance between the parallel quinone rings. Additionally, the pendant groups of the macrocycle will be modified to increase the solubility properties of the cambiarenes. This project should allow for the development of new small molecule and macrocyclic synthetic methodology, a greater understanding of the anion-pi interaction, and the establishment of the cambiarene as a useful supramolecular host molecule.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.

在化学系大分子、超分子和纳米化学项目的支持下，杰伊·W·中央学院的Wackerly计划设计和合成一类具有“捕获和释放”能力的新“宿主”分子。 “主体”分子有一个空腔，较小的“客体”分子可以装入其中。 这类新型宿主的两个独特特征是：1）模块化框架，能够控制宿主的大小、形状和电子性质，以选择性结合特定的客体目标，以及2）可切换的电子性质，允许结合目标被打开和关闭。 将研究富电子客体分子和带负电荷离子（如卤素离子和磷酸根离子）的结合特性和可逆捕获和释放。 该研究旨在获得对分子间相互作用的更深入的基本理解，并为水净化和废物处理的分子受体设计提供见解。 该项目将为本科生，包括代表性不足群体的学生提供研究培训机会。 研究成果将融入本科实验课程和初高中科学课堂的科学演示，以激发学生对科学的兴趣。 这些超分子主体大环的一个值得注意的方面是，它们可以改变它们的电子状态时，由于两个平行面对醌环的存在下，受到氧化还原刺激。这类结构被命名为“cambiarene”，来自拉丁语“cambiare”，意思是“改变”。本研究将探讨如何嵌入醌环可以调制，以产生不同的结构，电子和绑定性能。含有醌环的大环的上缘将从原始形式延长和缩短，以研究如何在腔体内容纳不同大小的客人，以及客人如何强烈结合，特别注意阴离子-π相互作用的贡献。大环的下边缘将被修改以控制空腔大小和平行醌环之间的距离。此外，大环的侧基将被修饰以增加cambiarene的溶解度性质。该项目应允许开发新的小分子和大环合成方法，更好地理解阴离子π相互作用，并建立cambiarene作为一个有用的超分子主体molecular.This奖项反映了NSF的法定使命，并已被认为是值得通过使用基金会的智力价值和更广泛的影响审查标准进行评估的支持。