CONVEX POLYCYCLES: SYNTHESIS, STRUCTURE, AND CHEMISTRY OF HETEROTRIQUINANES

在这个由化学系化学合成计划资助的项目中，加州戴维斯大学化学系的Mark Mascal教授将通过合成包含大量空间的有机多环来探索分子曲率和电子学的基本原理，从凹面到半球形，再到完全封闭的壳体。 该研究计划围绕着triquinane分子框架，一个刚性，碗状，融合三轮车。 合成兴趣的关键特征是氧化杂三醌到非平面芳族半富勒烯片段，以及将这种结构构建成杂十二面体的前景。 三醌平台稳定了通常仅作为反应性中间体的化学物质，如叔氧鎓盐、氧鎓叶立德和四价恶二鎓离子。 除了基本的科学影响外，鉴于纳米技术领域对弯曲芳香表面的持续兴趣，该项目有可能对应用材料科学做出重大贡献。 在培训和多样性方面的更广泛的影响在于该计划的跨学科性质，包括在各个点有机合成，非共价键，配位化学，活性中间体，超价，芳香性，晶体学，理论化学和纳米技术方面的问题。 主要的教育成果是研究纳入本科化学实验室课程和促进本科研究，特别是涉及代表性不足的群体，通过参与专门的，大学赞助的计划。 外展涉及参与ACS项目种子，加州大学戴维斯分校青年学者计划和加州大学宇宙计划。

In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Mark Mascal of the Department of Chemistry at the University of California Davis will explore the fundamentals of molecular curvature and electronics by synthesizing organic polycycles that enclose volumes of space, from concave, to hemispherical, to completely closed shell bodies. The research program revolves around the triquinane molecular framework, a rigid, bowl-shaped, fused tricycle. Key features of synthetic interest are the oxidation of heterotriquinanes to nonplanar aromatic hemi-fullerene fragments, and the prospect of building out such structures into heterododecahedranes. The triquinane platform stabilizes chemical species that are normally seen only as reactive intermediates, such as tertiary oxonium salts, oxonium ylides, and tetravalent oxadionium ions. In addition to the fundamental scientific impact, this project has the potential to contribute substantially to applied material science, in view of the continuing interest in curved aromatic surfaces in the area of nanotechnology. The broader impacts in terms of training and diversity lie in the program's interdisciplinary nature, encompassing at various points organic synthesis, noncovalent bonding, coordination chemistry, reactive intermediates, hypervalency, issues in aromaticity, crystallography, theoretical chemistry, and aspects of nanotechnology. Principal educational deliverables are the incorporation of research into undergraduate chemistry laboratory courses and the promotion of undergraduate research, particularly involving under-represented groups, through the involvement in dedicated, university-sponsored programs. Outreach involves participation in the ACS Project SEED, the UC Davis Youth Scholars Program, and the UC COSMOS program.