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化学合成计划支持托马斯·R·霍耶教授的这一项目。霍耶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，允许合成被称为多环芳烃的新分子。这些分子有价值的原因有很多，其中之一是它们在光电设备中的潜力，如有机发光二极管(OLED)和光伏电池，用于节能显示器、照明装置和将太阳能转换为电能。通过对用于制造多环芳烃的新反应有了基本的了解，霍伊教授和他的同事们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，并在未来建立性能更好的新材料。该项目对广泛的利益相关者群体产生了许多重大的、更广泛的影响。特别值得注意的是为本科生提供的研究机会，关于复杂有机混合物的实用分离的教程，以及明尼苏达州博览会“可持续聚合物”展览的新扩展。Hoye教授的研究小组正在利用六氢-Diels-Alder(HDDA)反应级联的巨大潜力，提供多种类型的高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研究领域有价值。合作已经到位，以寻求此类开发的早期阶段。这类化合物的合成方法和策略是这一项目中最重要的“产品”。初步结果表明，合成路线往往非常短和有效。新的、根本上重要的机械论知识也在不断涌现。苯并炔化学的新进展包括环加成反应、双向苯并炔捕获和受控齐聚物的合成。一种被称为“多米诺骨牌-HDDA反应”的过程尤其耐人寻味。霍伊教授拥有重要的教学奖项，以表彰他在职业生涯中对本科生和研究生教育的长期承诺。该项目支持的外展活动惠及多个层次的化学研究学生，并有助于在绿色化学和可持续聚合物领域对公众进行教育。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、光伏和太阳能电池的环境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.