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.

在该项目中，由化学部的化学合成计划资助，德克萨斯大学奥斯汀分校化学系的迈克尔·克里斯切（Michael J.多环芳烃用于商业电子展示屏幕，并在其他一系列应用中表现出希望，例如高速电子和太阳能电池。该项目涉及跨越有机化学，均质过渡金属催化和材料化学领域的专业知识。 克里斯切教授的导师和培训本科生，研究生和博士后研究伙伴，包括科学历史上人数不足的团体的学生。 Krische教授建立并继续在德克萨斯州的全州有机化学研讨会共同组织，称为“ Texsyn”。这项吸引100名与会者的年度活动包括一场海报会议和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，以设计新的商品和精细化学品。迈克尔·克里斯切（Michael J. Krische）教授的实验室率先开创了一类新的催化碳碳键形成，这些碳键形成直接将较低的酒精转化为较高的酒精。这些过程绕过了化学计量金属的使用和离散的酒精到核糖氧化还原反应，这些反应是危险的，有助于产生废物。基于这种新的反应性模式，开发了二醇介导的苯济化反应。在NSF支持的宙斯盾下，这种苯济化方法将用于推进新策略，以合成多环芳族烃和相关的纳米学材料，这在分子电子的不断增长领域至关重要。虽然多环芳族烃合成的领域主要依赖于交叉耦合技术，但这种二醇介导的苯济体可以解锁广泛的新型多环芳芳烃化学空间。该奖项反映了NSF的立法任务，并被认为是通过使用基础知识的智力效果和广泛的Crictiation和Broadite Croctiation和Broadite Croctiation进行评估。

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.