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

利用六氢狄尔斯-阿尔德 (HDDA) 反应轻松合成精制多环芳烃

基本信息

批准号：
1665389
负责人：
Thomas Hoye
金额：
$ 49.27万
依托单位：
University of Minnesota-Twin Cities
依托单位国家：
美国
项目类别：
Continuing Grant
财政年份：
2017
资助国家：
美国
起止时间：
2017-07-01 至 2022-02-28
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1665389&HistoricalAwards=false
关键词：
Using Hexadehydro Diels Alder HDDA

项目摘要

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.

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·霍伊教授的项目。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，可以合成称为多环芳烃的新型分子。这些分子因多种原因而具有价值，其中之一是它们在光电器件中的应用潜力，例如有机发光二极管 (OLED) 和光伏电池，用于节能显示器、照明装置以及太阳能转换转化为电力。通过对用于制造多环芳烃的新反应有了基本的了解，霍耶教授和他的同事们可能会推动化学反应合成具有先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。该项目对广大利益相关者群体产生了许多重大、更广泛的利益影响。特别值得注意的是本科生研究生的研究机会、复杂有机混合物的实际分离教程以及明尼苏达州博览会“可持续聚合物”展览的新扩展。霍耶教授的研究小组正在利用十六氢的巨大潜力-Diels-Alder (HDDA) 反应级联，用于快速化学合成多种类型的高度共轭多环芳烃。有些对有机电子和光子材料研究领域有价值。合作已经到位，以实现此类开发的早期阶段。合成此类化合物的方法和策略是该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且有效。新的、根本上重要的机械知识也在不断出现。苯炔化学的进展包括环加成反应、双向苯炔捕获和受控低聚物合成的新方面。一个被称为“多米诺骨牌-HDDA 反应”的过程特别有趣。霍伊教授获得了多项重要教学奖项，以表彰他在职业生涯中对本科生和研究生教育的承诺。该项目支持的外展活动使多个层次的化学研究学生受益，并为绿色化学和可持续聚合物领域的公众教育做出了贡献。科学进步有可能为材料科学家在发光二极管、光伏和太阳能电池中使用有机电子和光子化合物的追求开辟新的途径。这些应用程序具有巨大的社会影响潜力。