Functionalizing Polyaromatic Materials with Boranes and Borenium Ions

多环芳烃（PAHs）是一种大的平面分子，电子可以很容易地通过它流动。它们广泛应用于有机电子学、化学传感器、催化和生物成像等领域。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，用于光动力治疗、光刻、荧光防伪方法和开关。多环芳烃的性质可以通过在这些大分子的外围附加不同的化学基团来控制。在多环芳烃的许多应用中，发现这种连接的新基团对提高多环芳烃的性能非常重要。罗格斯大学纽瓦克分校化学系的Frieder jaeckle教授在化学合成计划的支持下，制备了含有附着的硼氮基团的多环芳烃。明智地选择硼氮单元的位置，可以对电子特性进行微调，从而最大限度地响应生理或环境变化。这些多环芳烃被整合到聚合物中，以提高其耐久性，并被开发用于从电子元件到分子开关的各种应用。此外，该项目有助于在有机、无机和材料化学界面的跨学科研究环境中培养多样化的学生群体。贾克尔博士将组织外展项目，让当地高中的学生和他们的老师亲身体验研究，并了解STEM领域的就业机会。研究小组通过ACS项目SEED招募高中暑期学生，该项目旨在支持社会经济上处于不利地位的学生。在这个项目中，多环芳烃和相关的偶联多芳烃被B-N路易斯对功能化，应用于从有机电子到分子开关等领域。一个方向侧重于特定地点的功能手柄的引入，允许对光电特性进行微调。通过对功能化的合理选择，可以系统地改变空间应变和随之产生的扭曲。在扭曲的极限下，封闭和开放结构可能共存，从而产生刺激响应特性。硼离子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为广泛离域的中性物质。这些功能多环芳烃集成到聚合物系统和它们的附着量子点进行了研究。这项研究还得到了鼓励来自代表性不足群体的学生参与的努力的补充。该奖项反映了美国国家科学基金会的法定使命，并通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。

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.