Homologs and Substructures of

这项研究的重点是合成一种扩展版本的“立方体石墨”的若干亚结构或碎片。这些碎片的分子式从C168H116到C672H432，包含大的空腔和通道。基本重复单元是六苯基苯分子，在苯基的对位连接在一起。钯催化的偶联反应(铃木偶联)将使用六苯基苯的简单衍生物进行。将制备大约十个六苯基苯的卤代或含有机硼的衍生物作为构建块，并将从这个文库中制备各种亚结构。将尝试这些亚结构的环脱氢反应，可能是为了产生立方体石墨的同系物，其中苯环已被六苯并冠烯取代。尽可能多的目标分子将用单晶X射线衍射法进行表征。有了这个新的奖项，有机化学和高分子化学计划将支持普林斯顿大学化学系的罗伯特·A·帕斯卡博士的研究。帕斯卡教授将把他的工作重点放在合成大的多苯基芳香化合物上。这些化合物是基于所谓的“立方石墨”的结构，这是一种假想的碳的同素异形体，由在立方空间群中三维相互连接的苯环组成。这些化合物可能具有主客体应用或用于分离技术。就更广泛的影响而言，帕斯卡小组已被证明是培训本科生和研究生的极好场所。

The focus of this research is the synthesis of a number of substructures or fragment of an expanded version of "cubic graphite." These fragments, with formulae ranging from C168H116 to C672H432, contain large cavities and channels. The fundamental repeating units are hexaphenylbenzene molecules, linked together at the para positions of the phenyl groups. Palladium catalyzed coupling reactions (Suzuki couplings) will be carried out using simple derivatives of hexaphenylbenzene. Approximately ten halogenated or organoboron-containing derivatives of hexaphenylbenzene will be prepared as building blocks, and from this library, a variety of substructures will be made. The cyclodehydrogenation of these substructures will be attempted, perhaps to yield yield homologs of cubic graphite where benzene rings have been replaced by hexabenzocoronenes. As many of the target molecules as possible will be characterized by single crystal X-ray diffraction methods.With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Robert A. Pascal of the Department of Chemistry at Princeton University. Professor Pascal will focus his work on the synthesis of large polyphenyl aromatic compounds. The compounds are based on the structure of so-called "cubic graphite," a hypothetical allotrope of carbon composed of benzene rings interconnected in three dimensions in a cubic space group. The compounds could have host-guest applications or use in separation technology. In terms of broader impacts, the Pascal group has proven to be an excellent venue for the training of both undergraduate and graduate students.