CONVEX POLYCYCLES: SYNTHESIS, STRUCTURE, AND CHEMISTRY OF HETEROTRIQUINANES

在这个由NSF化学部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教授正在探索分子曲率和电子学的基本方面。这个项目有可能大大有助于应用材料科学，因为在纳米技术领域弯曲的芳香表面的相关性。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，包括有机合成，非共价键，配位化学，活性中间体，高价，芳香性，晶体学，理论化学和纳米技术。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。拓展包括参与NSF本科生研究经验计划，ACS项目SEED，加州大学戴维斯分校青年学者计划和加州大学COSMOS计划。该项目涉及合成有机多环化合物，这些多环化合物包围了大量的空间，从凹面到半球形，再到完全封闭的壳体。该研究计划围绕三醌分子框架展开，该框架由三个环以刚性、褶皱的排列融合在一起。合成兴趣的关键特征是将杂三醌氧化成碗状芳香半富勒烯片段，以及将这种结构构建成球形杂十二面体的前景。三醌平台还稳定了通常只被视为反应性中间体的化学物质，如叔氧鎓盐、氧鎓叶立德，甚至四价恶二鎓离子。

In this project funded by the Chemical Synthesis Program of the NSF Chemistry Division, Professor Mark Mascal of the Department of Chemistry at the University of California Davis is exploring fundamental aspects of molecular curvature and electronics. This project has the potential to substantially contribute to applied material science because of the relevance of 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 organic synthesis, noncovalent bonding, coordination chemistry, reactive intermediates, hypervalency, aromaticity, crystallography, theoretical chemistry, and 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 NSF Research Experiences for Undergraduates program, ACS Project SEED, the UC Davis Youth Scholars Program, and the UC COSMOS program.The project involves 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, which comprises three rings fused together in a rigid, puckered arrangement. Key features of synthetic interest are the oxidation of heterotriquinanes to bowl-shaped aromatic hemi-fullerene fragments, and the prospect of building up such structures into spherical heterododecahedranes. The triquinane platform also stabilizes chemical species that are normally seen only as reactive intermediates, such as tertiary oxonium salts, oxonium ylides, and even tetravalent oxadionium ions.