Borane Modification of Polycyclic Aromatic Hydrocarbons

化学部化学合成计划支持Frieder Jaekle教授的项目。Jaekle教授是罗格斯大学纽瓦克校区化学系的教员。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。硼的存在增加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建立有机电子、成像、传感器、分子开关等的有效平台。在这些环境中，当材料与富电子给体或贫电子受主原子“掺杂”时，它们的性能会得到改善，从而提高导电性。虽然多环芳烃与氮和硫(两种给体)的掺杂已经得到了广泛的研究，但对与其他杂原子的体系的研究仍然不太发达。硼是非常有趣的，因为它的贫电子(受主)特性可以导致新的，理想的光电设备性能。Jaekle教授和他的学生们已经做好了制造和研究掺硼多环芳烃的准备，以充分开发它们的潜力。该项目还有助于在有机、无机化学和材料化学交界处的跨学科研究环境中培训不同的学生群体。另一个目标是通过组织研讨会、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，以寻求新的共轭杂化材料。该研究的具体目的是：(1)通过Lewis碱定向的亲电C-H硼化反应，开发区域选择性的多环芳烃外围官能化方法；(2)开发将多个三配位硼中心纳入多环芳烃框架的新方法；(3)研究硼掺杂/官能化对多环芳烃的电子结构、光物理性质和化学反应活性的影响。开发了新的合成工具，提供了获得具有定制性质的独特功能pi共轭体系的途径。将硼烷战略性地放置在多环芳烃外围或骨架中明确定义的位置上，预计将极大地改变其电子结构。新的聚酰亚胺共轭杂化材料的制备有望带来具有理想的光学、电学、刺激响应和感官性能的新材料。与这项研究相辅相成的是，努力吸收代表性不足群体的学生参与国际和跨学科合作，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.