Diol-Mediated Benzannulation for Polyaromatic Hydrocarbon (PAH) Construction

二醇介导的苯并环化用于多芳烃 (PAH) 的构建

• 批准号: 1855744
• 负责人: Michael Krische
• 金额: $ 48万
• 依托单位: University of Texas at Austin
• 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: 2019-07-01 至 2023-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1855744&HistoricalAwards=false
• 关键词: Diol; Mediated; Benzannulation; Polyaromatic; Hydrocarbon

In this project, funded by the Chemical Synthesis Program of the Chemistry Division, Professor Michael J. Krische of the Department of Chemistry at the University of Texas at Austin is applying catalytic reactions developed in his laboratory to the construction of polycyclic aromatic hydrocarbons. Polycyclic aromatic hydrocarbons are used in commercial electronic display screens and show promise in a range of other applications, for example, high-speed electronics and solar cells. The project involves expertise spanning the fields of organic chemistry, homogenous transition metal catalysis, and materials chemistry. Professor Krische mentors and trains undergraduates, graduate students and postdoctoral research associates, including students from groups historically underrepresented in the sciences. Professor Krische founded and continues to co-organize a state-wide organic chemistry symposium in Texas, known as ?TEXSYN.? This annual event, which attracts 100 attendees, includes a poster session and short talks by undergraduate and graduate students, connecting students with leading researchers to design new routes to commodity and fine chemicals. Professor Michael J. Krische's laboratory has pioneered a new class of catalytic carbon carbon bond formations that directly convert lower alcohols to higher alcohols. These processes bypass the use of stoichiometric metals and discrete alcohol-to-carbonyl redox reactions, which are hazardous and contribute to waste generation. Based on this new reactivity pattern, diol-mediated benzannulation reactions were developed. Under the aegis of NSF support, this benzannulation methodology will be used to advance new strategies for the synthesis of polycyclic aromatic hydrocarbons and related nanographene materials, which are of significant importance in the growing field of molecular electronics. Whereas the field of polycyclic aromatic hydrocarbon synthesis is largely reliant on cross-coupling technology, this diol-mediated benzannulations could unlock broad and new polycyclic aromatic hydrocarbon chemical space.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.

在这项由化学系化学合成计划资助的项目中，德克萨斯大学奥斯汀分校化学系的Michael J.Krische教授将其实验室开发的催化反应应用于多环芳烃的构建。多环芳烃被用于商业电子显示屏，并在一系列其他应用中显示出希望，例如高速电子和太阳能电池。该项目涉及有机化学、均相过渡金属催化和材料化学等领域的专业知识。Krische教授指导和培训本科生、研究生和博士后研究助理，包括来自科学界历史上代表性不足的群体的学生。Krische教授在德克萨斯州创办并继续共同组织了一个全州范围的有机化学研讨会，被称为？TEXSYN。这个一年一度的活动吸引了100人参加，包括一个海报会议，以及本科生和研究生的简短演讲，将学生与领先的研究人员联系起来，设计通向大宗商品和精细化学品的新路线。Michael J.Krische教授的实验室开创了一种新的催化碳碳键形成方式，可以将低级醇直接转化为高级醇。这些过程绕过了化学计量金属和离散的醇到羰基氧化还原反应的使用，这两种反应都是危险的，并有助于产生废物。基于这一新的反应模式，发展了二醇介导的苯环化反应。在NSF的支持下，这种苯环方法将被用来提出合成多环芳烃和相关纳米材料的新策略，这些材料在日益增长的分子电子学领域具有重要意义。尽管多环芳烃合成领域在很大程度上依赖于交叉偶联技术，但这种二元醇介导的苯环反应可以打开广阔的和新的多环芳烃化学空间。这一奖项反映了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。

项目成果

Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings.

• DOI: 10.1021/acs.chemrev.0c01133
• 发表时间: 2021-04-14
• 期刊: Chemical reviews
• 影响因子: 62.1
• 作者: Doerksen RS;Hodík T;Hu G;Huynh NO;Shuler WG;Krische MJ
• 通讯作者: Krische MJ

Synthesis and Photophysical Properties of Soluble N‐Doped Rubicenes via Ruthenium‐Catalyzed Transfer Hydrogenative Benzannulation

钌催化转移氢化苯环化合成可溶性N掺杂Rubicenes及其光物理性质

• DOI: 10.1002/chem.202100134
• 发表时间: 2021
• 期刊: Chemistry – A European Journal
• 作者: Shuler, William G.;Parvathaneni, Sai P.;Rodriguez, Jacob B.;Lewis, Taylor N.;Berges, Adam J.;Bardeen, Christopher J.;Krische, Michael J.
• 通讯作者: Krische, Michael J.