CAREER: Constructing Conjugated Heteroarene Architectures via Ring-Expansion Reactions with Anti-Aromatic Boroles

当电流通过时会发光的材料有无数的应用，包括LED灯泡、计算机显示器和医疗成像设备。相反，当暴露在光线下时会产生电力的材料被用于包括太阳能转换在内的应用。虽然有许多材料具有这些特性，但在开发吸收或发射的光可以调整为特定颜色的材料方面存在挑战。贝勒大学化学与生物化学系Caleb Martin博士在化学系化学合成项目的支持下，制备了含有硼、磷或硫的材料，这些材料可以作为有机发光二极管（oled）和有机光伏（opv）。通过改变这些元素的数量，可以选择性地改变发射或吸收的光的颜色。这些发光/吸收单元被整合到聚合物中，形成可用于各种应用的柔性oled和opv。该项目还包括与韦科的非营利组织合作，为低收入和无家可归的学生提供服务。互动活动与该项目有关，其最终目标是帮助增加在STEM领域学习的低收入少数族裔的高等教育入学率。该项目的目标是合成含硼的苯类似物和其他扩展芳香化合物，其特征是硼和含有杂原子的孤对作为环中C=C单元的价等电子替代品。该合成路线涉及一种环扩展方法，该方法利用了抗芳硼孔试剂中内环硼碳键的不稳定性。研究了含硼杂芳烃的电子性质，重点研究了其在有机发光二极管（oled）和有机光伏（opv）中的应用。由于硼孔试剂的可及性，最初的目标是具有每芳基取代的单环体系。然而，为了减少HOMO-LUMO的间隙，通过形成多环体系来增加共轭性。通过与当地低收入和无家可归学生的非营利组织合作，正在组织与该项目相关的互动活动。这项推广活动的最终目标是帮助增加低收入、代表性不足的少数民族在STEM领域学习的高等教育入学率。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。

Materials that emit light when electricity is passed through them have a myriad of applications including LED light bulbs, computer displays, and medical imaging devices. Conversely, materials that generate electricity when exposed to light are used in applications including solar energy conversion. While there are a number of materials that have these properties, there is a challenge in developing ones in which the light that is absorbed or emitted can be tuned to specific colors. Dr. Caleb Martin, Department of Chemistry and Biochemistry, Baylor University, is supported by the Chemical Synthesis Program of the Chemistsry Division, to prepare materials containing boron and phosphorus or sulfur that function as organic light emitting diodes (OLEDs) and organic photovoltaics (OPVs). By varying the amounts of these elements the color of light that is emitted or absorbed can be selectively changed. These light emitting/absorbing units are incorporated into polymers to form flexible OLEDs and OPVs that can be used in a variety of applications. This project also contains outreach efforts through partnerships with non-profit organizations in Waco that serve low income and homeless students. Interactive activities are related to the project with the ultimate goal to help increase the post-secondary enrollment of low income underrepresented minorities pursuing studies in the STEM fields. The project's goals are to synthesize boron containing analogues of benzene and other extended aromatic compounds that feature boron and a lone pair containing heteroatom as valence isoelectronic substitutes for a C=C unit in the ring. The synthetic route involves a ring expansion methodology that takes advantage of the lability of the endocyclic boron-carbon bond in anti-aromatic borole reagents. The electronic properties of the boron containing heteroarenes are investigated computationally and spectroscopically with a focus on fluorescence and band gaps for application in organic light emitting diodes (OLEDs) and organic photovoltaics (OPVs). Due to the accessibility of the borole reagents, the initial targets are monocyclic systems with per-aryl substitution. However, in order to decrease the HOMO-LUMO gap conjugation is being increased by forming polycyclic systems. Through partnerships with local non-profit organizations for low income and homeless students, interactive activities that are related to this project are being organized. The ultimate goal of this outreach is to help increase the post-secondary enrollment of low income underrepresented minorities pursuing studies in the STEM fields.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.