CAREER: Convex Polycycles - Synthesis in the Azatriquinane Series

本课题主要研究含杂原子凸多环的合成。本研究将发展一种取代阿扎特里醌的合成方法，并研究所合成的手性阿扎特里醌酸、亲核试剂和配体的性质和应用。将制备并分析由氮杂醌衍生的新型融合三环10-pi芳香体系。阿扎三醌衍生物的固态二聚化将产生二氮十二面体烷。这些合成将由杂十二面体烷及其高级片段以及B-和对杂三醌体系的全合成来补充。这些研究为学生提供了有机合成、配位化学、晶体学以及手性、芳香性和纳米技术方面的广泛经验。在有机和大分子化学项目的职业奖的支持下，加州大学戴维斯分校化学系的马克·马斯卡尔教授正在探索分子的合成和性质，这些分子可以包裹一定的空间，无论是凹的、半球形的还是完全封闭的壳体。这种分子，也许是最广为人知的“富勒烯”（“巴基球”），既代表了化学科学中持久的魅力，也代表了具有潜在广泛技术应用的材料。这个项目为学生的基础研究提供了一个很好的训练基地。该项目还针对化学科学招聘和培训方面的一些其他发展，通过加强实验室课程的研究相关性，开发现代工业化学研究生课程，促进本科研究，设计学生参与考试过程的课程评估新方法，以及向区域社区学院和K-12机构提供普及服务。

This research program targets the synthesis of heteroatom-containing convex polycycles. A synthetic procedure for the alpha-substitution of azatriquinanes will be developed, and the properties and applications of resultant chiral azatriquinane-based acids, nucleophiles, and ligands will be investigated. Novel, fused tricyclic 10-pi aromatic systems derived from azatriquinacenes will be prepared and analyzed. Solid-state dimerization of azatriquinacene derivatives will yield diazadodecahedranes. These syntheses will be complemented by total syntheses of heterododecahedranes and advanced fragments thereof and of B- and P-heterotriquinane systems. These studies provide students with broad experience in organic synthesis, coordination chemistry, crystallography, and issues in chirality, aromaticity, and nanotechnology.With the support of this CAREER award from the Organic and Macromolecular Chemistry Program, Professor Mark Mascal, of the Department of Chemistry at the University of California at Davis, is exploring the synthesis and properties of molecules that envelop a volume of space, whether concave, hemispherical, or completely closed-shell bodies. Such molecules, perhaps most widely recognizable as the "fullerenes" ("Bucky balls"), represent both objects of enduring fascination in the chemical sciences and materials with potentially broad technological applications. This project serves as an excellent training ground for students in fundamental research. The project also targets a number of other developments regarding recruitment and training in the chemical sciences through enhancing the research relevance of laboratory courses, developing a modern industrial chemistry graduate course, promoting undergraduate research, and devising novel approaches to course assessment by student participation in the examining process, as well as providing popular outreach to regional community colleges and K-12 institutions.