Using the Hexadehydro-Diels-Alder (HDDA) Reaction for the Facile Synthesis of Elaborated Polycyclic Aromatics

美国国家科学基金会化学部的化学合成计划支持托马斯R.霍耶Hoye教授是明尼苏达大学化学系的教员。他正在开发新的化学反应，可以合成称为多环芳烃的新型分子。这些分子由于多种原因而有价值，其中之一是它们在光电器件中的潜在用途，例如在节能显示器、照明单元中使用的有机发光二极管（OLED）和光伏电池，以及用于将太阳能转化为电能。通过对用于制造多环芳烃的新反应的基本理解，Hoye教授和他的同事可能会将化学反应推向合成具有以前未知化学结构的化合物，并在未来构建具有改进性能的新材料。该项目产生了一些重大的广泛影响，使广大利益攸关方受益。特别值得一提的是为本科研究生提供的研究机会，复杂有机混合物的实际分离教程，以及明尼苏达州博览会展览“可持续聚合物”的新扩展。“Hoye教授的研究小组正在利用六脱氢-狄尔斯-桤木（HDDA）反应级联的巨大潜力，提供多种高度共轭多环芳烃的快速化学合成。其中一些对有机电子和光子材料的研究具有重要的意义。 目前正在进行合作，以推动这种发展的早期阶段。这是合成这些化合物的方法和策略，是从这个项目中出现的最重要的“产品”。初步结果表明，合成路线通常非常短和有效。新的和具有根本重要性的机械知识也正在出现。苯炔化学的进展包括环加成反应、双向苯炔捕获和可控低聚物合成的新方面。一个被称为“多米诺-HDDA反应”的过程特别有趣。霍耶教授持有主要的教学奖项，以表彰他在本科和研究生阶段对学生教育的长期承诺。该项目支持的外联活动使化学研究生在多个层面受益，并有助于公众在绿色化学和可持续聚合物领域的教育。这些科学进步有可能为材料科学家开辟新的途径，他们在发光二极管、光化学和太阳能电池的设置中使用有机电子和光子化合物。 这些应用具有巨大的社会影响潜力。

The Chemical Synthesis Program of the Chemistry Division of the NSF supports the project by Professor Thomas R. Hoye. Professor Hoye is a faculty member in the Department of Chemistry at the University of Minnesota. He is developing new chemical reactions that allow for the synthesis of novel molecules known as polycylic aromatics. These molecules are valuable for a variety of reasons, one being their potential for use in optoelectronic devices such as the organic light emitting diodes (OLEDs) and photovoltaic cells that are used in energy efficient displays, lighting units, and for the conversion of solar energy into electricity. By developing a fundamental understanding of the new reactions used to make polycyclic aromatics, Professor Hoye and his coworkers may push the chemical reactions toward the synthesis of compounds having previously unknown chemical structures and, in the future, build new materials with improved properties. A number of significant broader impacts of benefit to a wide group of stakeholders result from the project. Of particular note are research opportunities for undergraduate research students, a tutorial on the practical separation of complex organic mixtures, and new extensions of the Minnesota State Fair exhibit on "Sustainable Polymers."Professor Hoye's research group is capitalizing on the tremendous potential for the hexadehydro-Diels-Alder (HDDA) reaction cascade to provide for the rapid chemical synthesis of manifold classes of highly conjugated polycyclic aromatics. Some are of value to the field of organic electronic and photonic materials research. Collaborations are in place to pursue early phases of such development. It is the methods and strategies for the syntheses of such compounds that are the most important 'products' that are emerging from this project. Preliminary results demonstrate that the synthetic routes are often remarkably short and efficient. New and fundamentally important mechanistic knowledge is also emerging. Advances in the benzyne chemistry include new aspects of cycloaddition reactions, two-directional benzyne trapping, and controlled oligomer synthesis. A process dubbed the 'domino-HDDA reaction' is particularly intriguing. Professor Hoye holds major teaching awards that recognize his career-long commitment to the education of students at both the undergraduate and graduate levels. Outreach activities supported by this project benefit chemistry research students at multiple levels and contribute to the education of the public in the arenas of green chemistry and sustainable polymers. The scientific advances have the possibility of opening new avenues for pursuit by materials scientists who use organic electronic and photonic compounds in the settings of light-emitting diodes, photovoltaics, and solar cells. These applications have a large potential for societal impact.