Synthesis of cyclopenta-fused aromatic hydrocarbon radicals

环戊稠合芳烃基团的合成

• 批准号: 510793958
• 负责人: Professor Dr. Joachim Podlech
• 金额: --
• 依托单位: Institut für Organische Chemie (IOC)
• 依托单位国家: 德国
• 项目类别: Research Grants
• 资助国家: 德国
• 项目状态: 未结题
• 来源: https://gepris.dfg.de/gepris/projekt/510793958?language=en
• 关键词: Synthesis; cyclopenta; fused; aromatic; hydrocarbon

Conjugated systems, which alternately contain benzene and cyclopentadiene moieties (cyclopenta-fused polyaromatic hydrocarbons, CP-PAHs), are known for their special properties, making them, e.g., suitable for utilization in optoelectronic applications. CP-PAHs containing an odd number of five-membered rings are in their neutral state radicals. In this project radicalic CP-PAHs shall be synthesized by ortho-coupling in ortho-carboxyl- or ortho-formyl-substituted oligophenyls. The resulting intermediates shall be transferred into the conjugated CP-PAHs by oxidative or reductive methods. Side reactions at the radical centers can be prevented by bulky aryl substituents at the cyclopentadienes. Higher CP-PAHs should favorably be constructed starting with oligoaryls containing fluorene moieties. Methods are described for the synthesis of CP-PAHs containing up to eleven rings. The target compounds shall be investigated (partly in cooperation with other groups) with respect to their aromatic, electronic, and magnetic properties and their redox activities. The experimental analytical methods will be supported by quantum chemical calculations.

共轭体系交替地含有苯和环戊二烯部分（环戊二烯稠合的多环芳烃，CP-PAH），因其特殊性质而闻名，使它们，例如，适用于光电子应用。含有奇数个五元环的CP-PAHs处于中性状态自由基。在本项目中，自由基CP-PAH将通过邻位羧基或邻位甲酰基取代的低聚苯基的邻位偶联来合成。产生的中间体应通过氧化或还原方法转化为共轭CP-PAH。在自由基中心的副反应可以通过在环戊二烯上的大体积芳基取代基来防止。更高的CP-PAH应该有利地从含有芴部分的低聚芳基开始构建。描述了用于合成含有多达11个环的CP-多环芳烃的方法。应研究目标化合物的芳香性、电子性和磁性及其氧化还原活性（部分与其他小组合作）。实验分析方法将得到量子化学计算的支持。