RUI: SYNTHESIS, STRUCTURE, AND REACTIVITY OF ALKYNE-LINKED OLIGOPHENYLENES AND CYCLOPHENYLENES

RUI：炔连接的低聚苯基和环苯基的合成、结构和反应性

• 批准号: 1856535
• 负责人: Derik Frantz
• 金额: $ 25万
• 依托单位: California Polytechnic State University Foundation
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2019
• 资助国家: 美国
• 起止时间: 2019-08-15 至 2024-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1856535&HistoricalAwards=false
• 关键词: RUI; SYNTHESIS; STRUCTURE; REACTIVITY; ALKYNE

In this project, funded by the Chemical Synthesis Program of the Chemistry Division, Professor Derik K. Frantz of the Department of Chemistry and Biochemistry at California Polytechnic State University, San Luis Obispo is developing three-dimensional, cyclic and multicyclic molecular structures. These unique molecules are of fundamental interest as the researchers explore their unusual properties and investigate their potential applications in functional materials. A versatile synthetic strategy permits the creative design and construction of a wide variety of these molecules, which contain nanometer-scale rings that are clamped or tethered by short, linear linkers (alkynes). Outside of the laboratory, the Broader Impacts of this work support Professor Frantz's efforts to improve student success and increase inclusivity in organic chemical education through the production and presentation of video lessons to help students understand challenging concepts and to supplement an active, engaging classroom experience.Professor Frantz and his undergraduate research group aim to synthesize and investigate a variety of alkyne-linked oligophenylenes and cyclophenylenes. The synthetic methodology incorporates alkyne linkers as templates for the generation of phenylene- and ethynylene-based macrocyclic and multicyclic systems. In the targeted structures, alkyne groups internally link macrocycles to form structures with constrained molecular geometries. The researchers are studying the effect that this constrain imparts on the molecules' static and dynamic structures and on their reactivities and properties. The constrained targets include highly strained systems, twisted and helical structures, and designs possessing interlinked units. To construct these molecules, the researchers will apply a synthetic strategy that features robust, transition metal-catalyzed, C-C bond-forming reactions. This transferrable and modifiable approach will generate a variety of creative and unprecedented structures. Undergraduate students contributing to this project are to have an immersive research experience and gain significant practical scientific training and familiarity with advanced organic chemical concepts.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.

本研究由化学系化学合成计划资助，德里克K.位于圣路易斯奥比斯波的加州理工州立大学化学与生物化学系的Frantz正在开发三维、环状和多环分子结构。这些独特的分子是研究人员探索其不寻常的性质和研究其在功能材料中的潜在应用的根本利益。一个多功能的合成策略允许创造性地设计和构建各种各样的这些分子，其中包含纳米级的环，这些环被短的线性连接体（炔）夹住或束缚。在实验室之外，这项工作的更广泛的影响支持教授弗朗茨的努力，以提高学生的成功，并通过视频课程的制作和演示，以帮助学生理解具有挑战性的概念，并补充积极的，教授和他的本科生研究小组的目标是合成和研究各种炔-连接的低聚亚苯基和亚环苯基。该合成方法采用炔连接基作为模板，用于生成基于亚苯基和亚乙炔基的大环和多环系统。在目标结构中，炔基内部连接大环以形成具有受限分子几何形状的结构。研究人员正在研究这种约束对分子的静态和动态结构以及它们的反应性和性质的影响。受约束的目标包括高应变系统、扭曲和螺旋结构以及具有互连单元的设计。为了构建这些分子，研究人员将采用一种合成策略，该策略具有强大的过渡金属催化的C-C键形成反应。这种可转移和可修改的方法将产生各种创造性和前所未有的结构。该奖项体现了NSF的法定使命，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，被认为值得支持。

项目成果

Intramolecular Diels–Alder Reaction of a Biphenyl Group in a Strained meta -Quaterphenylene Acetylene

应变间位四联苯乙炔中联苯基的分子内狄尔斯·阿尔德反应

• DOI: 10.1021/acs.joc.2c02280
• 发表时间: 2023
• 期刊: The Journal of Organic Chemistry
• 作者: Mittal, Komal;Pham, Ashley V.;Davis, Amanda G.;Richardson, Abigail D.;De Hoe, Clement;Dean, Ryan T.;Baird, Vi;McDonald, Ashley Ringer;Frantz, Derik K.
• 通讯作者: Frantz, Derik K.