Controlled synthesis of functionalized oligomers and polymers: Development of methods for the solid supported synthesis of quinoxalin-based oligomers using 1,2-diketosynthons for their investigation and application in materials science.

喹烯酮和喹喔啉是相关的物质类别，其在合成、生物和材料科学中的研究具有极大的兴趣。除了许多药学相关的性质之外，含喹喔啉的结构在材料科学领域中被广泛研究。特别地，可以由多于一个喹喔啉部分描述的化合物由于各种电子和结构性质而受到极大关注。喹喔啉被研究作为电荷转移复合物、新型磁性材料、有机半导体、电池电极、存储介质电极或新型OLED组件和太阳能电池的基础中的配体。还描述了双茚并吩嗪的自组装或其纤维形成以及螺旋结构的形成，其可用于开发新的功能材料，例如用于制备光学活性聚合物。该项目的目的是开发能够在固相上形成和衍生寡喹喔啉的方法。聚合物载体的使用旨在允许消除先前的合成限制，并因此产生新类别的寡-和后来的聚-喹喔啉。新开发的方法旨在提供可以以受控方式使用单个喹喔啉模块的灵活组合来形成寡喹喔啉的方法。模块在它们并入低聚物的方式上不同，并且通过使用不同的喹喔啉结构单元产生额外的多样性。为此目的，在固体载体上构建四种类型的模块，其导致线性组合成四种不同的低聚结构。低聚物的不同组成将对低聚物的整体结构、其三维形状以及材料性质具有显著影响。来自均相低聚物的低聚物合成的发现旨在能够合成迄今为止完全未知的其他低聚物结构变体。因此，将追求低聚物内的各种变化、各个模块之间的金属配位和共价键形成以及引入额外的连接基团。除了低聚物的合成之外，在固相上形成喹喔啉用于三聚喹喔啉的裂解，其可以被芳构化以得到六氮杂三萘衍生物。在最后一步中使用所开发的方法来测试合成物到其他表面的可转移性。其目的是展示在平面表面上的应用，以允许通过单个模块的受控连接来合成聚合物。

Quinoxalinones and quinoxalines are related substance classes whose investigations in synthetic, biological and materials science are of great interest. In addition to numerous pharmaceutically relevant properties, quinoxaline-containing structures are extensively studied in the field of materials science. In particular, compounds which can be described by more than one quinoxaline moiety are of great interest due to various electronic and structural properties. Quinoxalines are investigated as ligands in charge-transfer complexes, new magnetic materials, the basis for organic semiconductors, battery electrodes, electrodes for storage media, or novel OLED components and solar cells. The self-assembly of dichinoxalinophenazines or their fiber formation has also been described as well as the formation of helical structures, which can be used for the development of new functional materials, e.g. for the preparation of optically active polymers. The aim of this project is to develop methods that enable the formation and derivatization of oligo-quinoxalines on solid phases. The use of the polymeric support is intended to permit the abolition of previous synthetic limitations and, as a consequence, the generation of new classes of oligo- and later poly-quinoxalines. The newly developed methods are intended to provide methods by which a flexible combination of individual quinoxaline modules can be used in a controlled manner for the formation of oligo-quinoxalines. The modules differ in the way of their incorporation into the oligomer and additional diversity is generated by the use of different quinoxaline building blocks. For this purpose, four types of modules are to be constructed on the solid support, which lead in linear combination to four different oligomeric structures. The different constitution of the oligomers will have a significant influence on the overall structure of the oligomer, on its three-dimensional shape as well as on the material properties. The findings from the oligomeric syntheses for homogeneous oligomers are intended to enable the synthesis of further oligomeric structural variants, hitherto completely unknown. Thus, diverse variations within the oligomers, metal coordination and covalent bond formation between the individual modules, as well as the introduction of additional linker groups will be pursued. In addition to the synthesis of oligomers, the formation of quinoxalines on the solid phases is to be used for the cleavage of trimeric quinoxalines, which can be aromatized to give hexaazatrinaphthalene derivatives. The developed methods are used in the last step to test the transferability of the syntheses to other surfaces. The aim is to demonstrate an application on planar surfaces in order to allow syntheses of polymers by controlled linkage of single modules.