CAREER: Convex Polycycles - Synthesis in the Azatriquinane Series

本研究的目标是合成含杂原子的凸多环化合物。将开发一种氮杂喹烷的α-取代的合成方法，并将研究得到的手性氮杂喹烷基酸、亲核剂和配体的性质和应用。从氮杂奎那烯衍生的新型稠合三环10-pi芳香族体系将被制备和分析。氮杂奎那烯衍生物的固相二聚反应将生成双氮杂十二面烷。作为这些合成的补充，杂十二面体及其高级碎片以及B-和P-杂三喹烷体系的全合成将是补充。这些研究为学生提供了在有机合成、配位化学、结晶学以及手性、芳香性和纳米技术方面的广泛经验。在有机和高分子化学项目的这一职业奖的支持下，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包裹大量空间的分子的合成和性质，无论是凹体、半球体还是完全封闭的壳体。这种分子，可能是最广为人知的“富勒烯”(“巴基球”)，既代表了化学科学中经久不衰的魅力对象，也代表了具有潜在广泛技术应用的材料。这个项目为学生提供了一个很好的基础研究培训基地。该项目还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，促进本科生研究，通过学生参与考试过程设计新的课程评估方法，以及向区域社区学院和K-12机构提供广受欢迎的外联，还针对化学科学的招聘和培训方面的其他一些发展。

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.