Functionalizing Polyaromatic Materials with Boranes and Borenium Ions

多环芳烃（PAH）是一种大的平面分子，电子可以很容易地通过它。它们在有机电子学、化学传感器、催化和生物成像中得到了广泛的应用。此外，一些多环芳烃可以提供一种不寻常的氧，称为单线态氧，用于光动力疗法，光刻，荧光防伪方法和开关。多环芳烃的性质可以通过将各种化学基团连接到这些大分子的外围来控制。发现新的连接基团对于改善多环芳烃在许多应用中的性能具有重要意义。罗格斯大学纽瓦克分校化学系的Frieder Jaekle教授得到化学合成计划的支持，以制备含有硼氮基团的多环芳烃。硼-氮单元的位置的明智选择允许微调电子特性，其用于最大化对生理或环境变化的响应。这些多环芳烃被整合到聚合物中，以提高其耐用性，并被开发用于从电子元件到分子开关的应用。此外，该项目有助于在有机，无机和材料化学的界面跨学科研究环境中培养不同群体的学生。 Jaekle博士将组织外展计划，让当地高中的学生和他们的老师亲身体验研究，并了解STEM领域的职业机会。 该研究小组通过旨在支持社会经济弱势学生的ACS SEED项目招募高中暑期学生。在本计画中，多环芳香族碳氢化合物及相关的π共轭多环芳香族化合物被B-N刘易斯对官能化，以应用于从有机电子学到分子开关等领域。一个方向侧重于特定于站点的功能手柄，允许微调的光电性能的介绍。通过官能化的明智选择，空间应变和随后的扭曲系统地变化。在扭曲的极限，封闭和开放的结构可能共存，从而产生刺激响应特性。Borenium离子的形成被用来产生高度缺电子的带电系统，这些系统在中等电位下被还原成广泛离域的中性物质。这些功能的多环芳烃的集成到聚合物系统和它们的附着到量子点的追求。该奖项反映了NSF的法定使命，并被认为值得通过使用基金会的智力价值和更广泛的影响审查标准进行评估来支持。

Polycyclic aromatic hydrocarbons (PAHs) are large, planar molecules through which electrons can easily flow. They have found widespread use in organic electronics, as chemical sensors, in catalysis, and in bioimaging. In addition, some PAHs can provide an unusual type of oxygen, called singlet oxygen, for applications in photodynamic therapy, lithography, fluorescent anti-counterfeiting methodologies, and switches. The properties of PAHs can be manipulated by attaching various chemical groups to the periphery of these large molecules. The discovery of new groups for such attachment is important to improving the performance of PAHs in their many applications. Professor Frieder Jaekle, Chemistry Department, Rutgers University – Newark, is supported by the Chemical Synthesis Program to prepare PAHs that contain attached boron-nitrogen groups. The judicious choice of the site of the boron-nitrogen unit allows for the fine-tuning of electronic properties, which are utilized to maximize responses to physiological or environmental changes. These PAHs are integrated into polymers to improve their durability and are developed for applications ranging from electronic components to molecular switches. Additionally, the project contributes to the training of a diverse group of students in an interdisciplinary research environment at the interface of organic, inorganic and materials chemistry. Dr. Jaekle will organize outreach programs that allow students and their teachers from local high schools to experience research first-hand and to lear about career opportunities in STEM fields. The research group recruits high school summer students through that ACS Project SEED which is aimed at supporting socio-economically disadvantaged students. In this project, polycyclic aromatic hydrocarbons and related pi-conjugated polyaromatic species are functionalized with B-N Lewis pairs for applications in areas ranging from organic electronics to molecular switches. One direction focuses on the site-specific introduction of functional handles that allow for the fine-tuning of the optoelectronic properties. Through the judicious choice of functionalization, the steric strain and the ensuing contortions are systematically varied. At the limits of distortion, closed and open structures may coexist, giving rise to stimuli-responsive properties. Borenium ion formation is exploited to generate highly electron-deficient charged systems that undergo reduction to extensively delocalized neutral species at moderate potentials. The integration of these functional PAHs into polymeric systems and their attachment to quantum dots is pursued. The research is complemented by efforts to encourage participation of students from underrepresented groups.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.