Synthesis and Recognition Properties of Cucurbit[n]uril Type Receptors

集装箱有各种各样的用途，比如保存食物，组织物品的集合，以及在运送到特定目的地的过程中保存物品。在化学领域，分子容器被用来隔离有气味的分子，通过不让不稳定化合物与其他分子反应来延长它们的寿命，并改变重要的分子性质，如溶解度。在马里兰大学，莱尔·艾萨克斯（Lyle Isaacs）教授的研究小组研究了下一代分子容器——葫芦素。通过制造一系列新的葫芦类容器，研究它们的基本容器特性，并展示它们如何集成到复杂的系统中，艾萨克斯的团队使其他学术和工业实验室能够将葫芦类分子容器应用于药物输送和对成瘾非处方药的感知等应用。Isaacs的研究数据用于通过蛋白质和配体建模（SAMPL）挑战的统计评估程序来刺激与计算化学家的相互作用。研究人员还与幼儿园开展外展活动，并分发用于光谱方法课程的问题集。研究重点是葫芦[n]uril （CB[n]）家族分子容器化合物的合成和超分子化学的发展。该项目的一个重要目标是发展结构亲和关系，以完善对CB[n]对阳离子类金刚石分子的异常紧密结合亲和关系的理解。新的无环葫芦比脲容器具有三甲烯衍生的芳香壁，允许对表面进行剪裁，以实现手性识别和客体选择性。通过将CB[n]容器与金属有机多面体连接，研究小组研究了客人如何在CB[n]容器内被吸收，进一步促进了金属有机多面体内的化学反应性。该奖项反映了美国国家科学基金会的法定使命，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。

Containers have a variety of uses, such as to preserve foodstuff, to organize collections of objects, and to hold objects during their shipment to specific destinations. In the chemistry realm, molecular containers are used to isolate molecules that smell, to extend the lifetime of unstable compounds by not allowing them to react with other molecules, and to change important molecular properties like solubility. At the University of Maryland, Professor Lyle Isaacs' research group studies next generation molecular containers known as cucurbiturils. By creating a series of new cucurbituril-type containers, studying their basic container properties, and showing how they may be integrated into complex systems, the Isaacs' group enables other academic and industrial labs to adapt cucurbituril molecular containers to applications such as drug delivery and sensing of addictive over-the-counter drugs. Isaacs' research data is used to stimulate interactions with computational chemists via the program Statistical Assessment of the Modeling of Proteins and Ligands (SAMPL) Challenges. The researchers also conduct outreach activities with pre-schools, and disseminate problem sets for use in spectroscopic methods courses.The research focuses on the development of the synthetic and supramolecular chemistry of a family of molecular container compounds called cucurbit[n]uril (CB[n]). An important aim of this project is to develop structure affinity relationships that refine the understanding of the extraordinarily tight binding affinity of CB[n] toward cationic diamondoid molecules. The new acyclic cucurbituril containers have triptycene derived aromatic walls that allow tailoring of the surface to enable chiral recognition and guest selectivity. By linking the CB[n] containers to metal-organic polyhedra, the research team investigates how guests are take up inside the CB[n] containers, further promoting chemical reactivity inside the metal-organic polyhedra.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.