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

在这个由化学部化学合成计划资助的项目中，圣路易斯奥比斯波加州理工大学化学和生物化学系的德里克·K·弗兰茨教授正在开发三维、环状和多环分子结构。随着研究人员探索它们的不同寻常的性质并研究它们在功能材料中的潜在应用，这些独特的分子引起了人们的根本兴趣。多才多艺的合成策略允许创造性地设计和建造各种各样的此类分子，这些分子包含纳米级的环，这些环被短的线性连接物(炔烃)夹住或拴住。在实验室之外，这项工作的更广泛的影响支持了Frantz教授的努力，通过制作和呈现视频课程来帮助学生理解具有挑战性的概念，并补充积极的、引人入胜的课堂体验，从而提高学生的学习成绩和增加有机化学教育中的包容性。Frantz教授和他的本科生研究小组旨在合成和研究各种炔基寡苯和环苯。该合成方法结合了炔基键作为模板，用于生成基于苯炔和乙炔的大环和多环体系。在目标结构中，炔基在内部连接大环，形成具有受限分子几何构型的结构。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度应变的系统、扭曲的和螺旋的结构，以及具有相互关联的单元的设计。为了构建这些分子，研究人员将应用一种合成策略，以过渡金属催化的C-C键形成反应为特征。这种可转移和可修改的方法将产生各种创造性和史无前例的结构。为该项目做出贡献的本科生将获得身临其境的研究体验，并获得重要的实用科学培训和对先进有机化学概念的熟悉。该奖项反映了NSF的法定使命，并通过使用基金会的智力优势和更广泛的影响审查标准进行评估，被认为值得支持。

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.