Borane Modification of Polycyclic Aromatic Hydrocarbons

化学部的化学合成项目支持弗里德·贾克尔教授的项目。杰克尔教授是罗格斯大学纽瓦克校区化学系的一名教员。他正在开发一种名为多环芳烃（PAHs）的新型共轭材料，这种材料含有含硼单元。硼的存在增强了多环芳烃作为光学和电子器件材料的潜力。为此，多环芳烃已被证明是构建有机电子、成像、传感器、分子开关等的有效平台。在这些环境中，当材料“掺杂”富电子的供体原子或电子贫乏的受体原子以增强导电性时，它们的性能得到改善。虽然对多环芳烃与氮和硫（都是供体）的掺杂进行了广泛的研究，但对其他杂原子体系的研究仍然较少。硼是非常有趣的，因为它的电子贫（受体）特性可以为光电器件带来新的、理想的性能。Jaekle教授和他的学生们完全有能力制造和研究硼掺杂的多环芳烃，以充分开发它们的潜力。该项目还有助于在有机、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。另一个目标是通过组织专题讨论会、国际合作和广泛传播该领域的新知识，将来自不同背景的研究人员聚集在一起，追求新的共轭杂化材料。本研究的具体目标是：(1)通过路易斯碱定向亲电C-H硼酸化，开发多环芳烃外围靶向功能化的区域选择性方法；(2)开发将多个三坐标硼中心纳入多环芳烃框架的新方法；(3)研究硼掺杂/功能化对电子结构、光物理性质和化学反应性的影响。新的合成工具的开发，提供了独特的功能pi-共轭体系，量身定制的性质。硼烷在多环芳烃外围或骨架的明确位置的策略性放置预计会显著改变其电子结构。新的π共轭杂化物的制备有望导致具有理想的光学，电子，刺激响应和感官性能的新材料。这项研究的补充工作是让代表性不足的群体的学生参与进来，参与国际和跨学科的合作，并为有机-无机杂化材料领域的研究人员提供科学交流的论坛。

The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Frieder Jaekle. Professor Jaekle is a faculty member in the Department of Chemistry at the Newark Campus of Rutgers University. He is developing new conjugated materials called polycyclic aromatic hydrocarbons (PAHs) that contain boron-containing units. The presence of the boron enhances the potential for the PAHs to serve as materials in optical and electronic devices. To this end, PAHs have proven to be effective platforms for building organic electronics, imaging, sensors, molecular switches, etc. In these settings, their performance is improved when the materials are "doped" with either electron-rich donor or electron-poor acceptor atoms that enhance conductivity. While the doping of PAHs with nitrogen and sulfur (both donors) has been studied extensively, research into systems with other heteroatoms remains less developed. Boron is very interesting as its electron-poor (acceptor) character can result in new, desirable properties for opto-electric devices. Professor Jaekle and his students are well-positioned to make and study the boron doped PAHs in order to fully develop their potential. The project also contributes to the training of a diverse group of students in an interdisciplinary research environment at the interface of organic, inorganic and materials chemistry. Another goal is to bring together researchers from different backgrounds in pursuit of new conjugated hybrid materials through organization of symposia, international collaborations, and broad dissemination of new knowledge in this field.The specific aims of the research are to: (1) develop regioselective methods for the targeted functionalization of PAHs at their periphery via Lewis base-directed electrophilic C-H borylation; (2) develop new approaches to incorporate multiple tricoordinate boron centers into the framework of PAHs; (3) investigate the effect of boron doping/functionalization on the electronic structure, photophysical properties, and chemical reactivity. New synthetic tools are developed that provide access to unique functional pi-conjugated systems with tailored properties. Strategic placement of boranes at well-defined positions in the periphery or framework of PAHs is expected to dramatically alter their electronic structure. The preparation of the new pi-conjugated hybrids is anticipated to lead to new materials with desirable optical, electronic, stimuli-responsive and sensory properties. The research is complemented by efforts to involve students from underrepresented groups, to engage in international and interdisciplinary collaborations, and to provide a forum for scientific exchange for researchers in the field of organic-inorganic hybrid materials.