Syntheses and Applications of Nonplanar Polycyclic Aromatic Compounds

本项目涉及利用高不饱和苯环烯的级联环化反应作为合成碗状（buckybowls）和篮状（buckybasket）多环芳烃化合物的关键步骤。总体策略包括首先构建含有多个四面体sp3杂化碳的前体。这些四面体sp3杂化碳的存在使分子的几个部分彼此靠近，通过温和的溶液化学进一步形成碳-碳键，从而形成巴克碗和巴克篮。所提出的合成方案的成功将为获得各种其他方法不易获得的此类化合物提供方便。此外，螺旋超分子组装和不对称催化也将合成螺旋型杂芳化合物。有机与大分子化学项目将通过该奖项支持西弗吉尼亚大学化学系王坤光教授的研究。王教授的研究重点是利用不饱和体系构建具有特殊结构的非平面有机分子。其中许多分子可能具有有趣的物质特性或生物活性。合成方法的成功发展将对化学和制药工业的制造过程产生影响。

This project involves the use of the cascade cyclization reactions of the highly unsaturated benzannulated enyne-allenes as a key step for the synthesis of bowl-shaped (buckybowls) and basket-like (buckybaskets) polycyclic aromatic compounds. The overall strategy involves first constructing precursors containing multiple tetrahedral sp3-hybridized carbons. The presence of these tetrahedral sp3-hybridized carbons causes several parts of the molecules to be in close proximity to one another, allowing further connections to form carbon-carbon bonds by mild solution-phase chemistry leading to buckybowls and buckybaskets. A success of the proposed synthetic schemes would provide easy access to a variety of such compounds not readily accessible by other methods. In addition, helical heteroaromatic compounds will also be synthesized for helical supramolecular assemblies and asymmetric catalysis.With this award the Organic and Macromolecular Chemistry Program is supporting the research of Professor Kung K. Wang of the Department of Chemistry at West Virginia University. Professor Wang's research efforts have focused on the use of unsaturated systems for the construction of nonplanar organic molecules having unusual architectures. Many of these molecules could possess interesting material properties or biological activities. Successful development of the synthetic methodology will have an impact on the manufacturing processes of the chemical and pharmaceutical industries.