Preparation and characterization of novel azomethine comonomers prepared from conjugated aminothiophene comonomers

共轭材料由于其物理性质而获得了广泛的重要性，使其成为发光器件和塑料电子器件的理想选择。其中最有吸引力的特性是它们的低氧化电位和光和电化学激发态，为电子器件提供合适的发射。不幸的是，这些所需材料的制备需要使用金属催化剂的严格反应条件，而金属催化剂难以去除。此外，用于制备此类材料的偶联方法导致具有不可靠性能的不一致产品。甲亚胺（-N=C-）共聚单体是理想的替代物，因为它们容易形成而无需严格的反应条件，具有一致的产物形成。当使用芳基前体时，所得键具有水解、还原和氧化抗性。所提出的是合成含有2或3个共价连接的含末端胺的噻吩的新型共聚单体。这提供了氨基联噻吩和三噻吩衍生物，其可以与各种芳族醛缩合，提供高度共轭的化合物。鉴于噻吩作为共轭聚合物前体的重要性，提出了使用Gewald反应从2，5-噻吩甲醛开始合成2，2 '-二氨基三噻吩。提出了噻吩的成熟取代化学来合成各种2，2 '-二氨基三噻吩衍生物。各种给电子体和吸电子基团可以容易地结合到3和4位中，除了增加溶解度之外，还允许微调物理性质。各种前体与芴和噻吩二醛的缩合将继续进行。由此产生的物理性质，包括氧化还原电位，荧光量子产率，激发态寿命，阳极电聚合，光谱电化学提出。

Conjugated materials have gained a wide importance because of their physical properties making them ideal for emitting devices and plastic electronics. Among the most attractive properties are their low oxidation potentials and photo- and electrochemically excited states affording suitable emissions for electronic devices. Unfortunately, the preparation of these desired materials requires stringent reaction conditions using metal catalysts that are problematic to remove. Furthermore, the coupling methods used to prepare such materials lead to inconsistent products with unreliable properties. Azomethines (-N=C-) comonomers are ideal alternatives because they are easily formed without stringent reaction conditions with consistent product formation. When using aryl precursors, the resulting bond is hydrolytically, reductively, and oxidatively resistant. What is proposed is the synthesis of novel comonomers containing 2 or 3 covalently linked thiophenes containing terminal amines. This affords amino bithiophene and terthiophene derivatives that can be condensed with various aromatic aldehydes affording highly conjugated compounds. Given the importance of thiophene as a precursor for conjugated polymers, the synthesis of 2,2'-diaminoterthiophene is proposed using the Gewald reaction starting from 2,5-thiophene carbaldehyde. The well established substitution chemistry of thiophene is proposed to synthesize various 2,2'-diaminoterthiophene derivatives. Various electron donors and withdrawing groups can be easily incorporated into the 3 and 4 positions allowing the fine tuning of the physical properties in addition to increasing the solubility. The condensation of the various precursors with fluorene and thiophene dialdehydes will be pursued. The resulting physical properties including the redox potentials, fluorescence quantum yields, the excited state lifetimes, anodic electropolymerization, and spectroelectrochemistry are proposed.