Syntheses and Structures of Functionalized [n]Cycloparaphenylenes and Related Carbon Nanohoops

有了这个奖项，化学合成计划是支持教授Kung K的基础研究。王在西弗吉尼亚大学。王教授将使用有机反应来构建一组称为cycloparaphenylenes（CPP）和相关碳纳米环的有机分子。CPP的结构代表扶手椅型碳纳米管的重复环状结构的最短片段。目前对CPP的强烈兴趣部分是由于使用这些环状分子作为生长扶手椅型单壁碳纳米管的模板的可能性。这种合成方法提供了一个潜在的优势，现有的经验方法在其潜力，以生产碳纳米管的均匀直径和结构安排，两个因素的关键重要性的应用在各种纳米技术领域，包括电子，能源和纳米光子器件。王教授将通过培训研究生设计新的合成策略，并为他们提供获得高水平实验室技能的机会，整合该项目的研究和教育部分。训练有素的合成有机化学家在他们参与这个研究项目的过程中的发展将增加化学和制药工业的人力资源。此外，被选中参加西弗吉尼亚大学NSF本科生研究经验计划和西弗吉尼亚大学夏季本科生研究经验计划的本科生将被邀请参加本研究项目。这些本科生中的许多人来自高等教育中代表性不足的人群，或者是第一代大学生。在大学期间提供让这些学生参与研究环境的机会将鼓励他们追求STEM职业。 本研究将为CPPs的合成提供新的方法。具体地，预期使用1，4-双（卤代芳基）-1，3-二烯和亲二烯体之间的狄尔斯-阿尔德反应来产生具有不同结构特征的官能化CPP和相关碳纳米环的前体。Diels-Alder反应的高立体选择性将使两个卤代芳基取代基位于所得环己烯基结构的同一侧，这对于随后的均偶联或交叉偶联步骤成功形成大环CPP前体至关重要。CPP前体与2，3-二氯-5，6-二氰基-1，4-苯醌或其它氧化剂的氧化芳构化预期导致相应的CPP。

With this award, the Chemical Synthesis program is supporting fundamental research of Professor Kung K. Wang at West Virginia University. Professor Wang will use organic reactions for the construction of a group of organic molecules called cycloparaphenylenes (CPPs) and related carbon nanohoops. The structures of CPPs represent the shortest segments of the repeating hoop-like structures of armchair carbon nanotubes. The intense current interest in CPPs is due in part to the possibility of using these hoop-like molecules as templates for growing armchair single-walled carbon nanotubes. This synthetic approach offers a potential advantage over existing empirical methods in its potential to produce carbon nanotubes of a uniform diameter and structural arrangement, two factors of critical importance for applications in a variety of nanotechnology fields, including electronics, energy, and nanophotonic devices. Professor Wang will integrate the research and educational components of this project by training graduate students in the design of new synthetic strategies and by providing them with the opportunities to acquire high-level laboratory skills. The development of well-trained synthetic organic chemists during the course of their involvements in this research project will add to the human resources for chemical and pharmaceutical industries. In addition, undergraduate students who are selected to participate in the West Virginia University NSF-Research Experiences for Undergraduates program and in the WVU Summer Undergraduate Research Experience program will be invited to participate in this research project. Many of these undergraduate students are from populations that are underrepresented in higher education or are first generation college students. Providing the opportunity to involve these students in a research environment during their college years will encourage them pursue careers in STEM. In this research, new methods will be developed for the synthesis of CPPs. Specifically, the use of the Diels-Alder reactions between 1,4-bis(haloaryl)-1,3-dienes and dienophiles are expected to produce precursors of functionalized CPPs and related carbon nanohoops with diverse structural features. The high stereoselectivity of the Diels-Alder reaction will place the two haloaryl substituents on the same side of the resulting cyclohexenyl structure, which is essential for the success of the subsequent homo- or cross-coupling step to form macrocyclic CPP precursors. Oxidative aromatization of the CPP precursors, either with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or other oxidizing agents, is expected to lead to the corresponding CPPs.