Boron-Nitrogen-Doped Conjugated Aromatic Hydrocarbons

在这个由NSF化学部化学合成计划资助的项目中，波士顿学院化学系的刘世元教授和他的学生合成了含硼氮（BN）的多环芳烃（PAH）。 这些分子表现出BN/CC（碳-碳）电子等排性，即它们用一个硼和一个氮原子取代芳香族有机分子中的两个碳原子。 虽然含碳-碳和含硼-氮的分子具有相同的总电子数，但它们的性质非常不同。 BN取代的多环芳烃可能在许多应用中有用，包括药物化学和将光转化为电的设备。 Liu团队正在开发新的合成方法来制造BN掺杂的PAH。 一旦准备好，分子被检查，看看它们与相关的含碳分子的反应如何不同。该计划的更广泛影响包括为当地公司的研究生提供工业实习，向当地高中提供科学推广，与国际研究人员合作，举办国际会议，以及通过促进代表性不足的群体参与的计划继续让本科生参与化学研究。硼氮/碳碳（BN/CC）电子等排，即，用一个硼原子和一个氮原子取代两个碳原子，已成为扩大材料科学相关化合物结构多样性的一种新策略。尽管最近在BN杂环化学方面取得了进展，但与有机材料的发展相关的多环芳烃的BN/CC电子等排体的系统探索仍然未被探索。本研究旨在发展一个全面的结构/反应性的关系，在BN电子等排体的简单并苯。研究计划包括：1）合成未报道的萘和蒽的母体BN电子等排体，2）表征合成材料的光电性质和化学反应性，3）开发多环芳烃的BN/CC电子等排体的预测能量模型。此外，这项研究为基础和应用化学合成的研究生和本科生研究人员提供了良好的培训。在这个项目中，学生参与者接触到各种实验方法和技术，通常应用于合成有机，无机，物理有机和有机金属化学。研究的跨学科和协作性质与外展活动相结合，与参与学生的教育和职业发展无缝集成。

In this project, funded by the Chemical Synthesis Program of the NSF Chemistry Division, Professor Shih-Yuan Liu and his students in the Department of Chemistry at Boston College synthesize boron-nitrogen(BN)-containing polycyclic aromatic hydrocarbons (PAHs). These molecules exhibit BN/CC (carbon-carbon) isosterism, that is, they replace two carbon atoms in an aromatic organic molecule with one boron and one nitrogen atom. While both the carbon-carbon and boron-nitrogen containing molecules have the same number of overall electrons, their properties are very different. BN-substituted PAHs may be useful in a number of applications including medicinal chemistry and devices that convert light to electricity. The Liu group is developing new synthetic methods to make BN-doped PAHs. Once prepared, the molecules are examined to see how they react differently than the related carbon-containing molecules. The broader impacts of this program include industrial internships for graduate students at local companies, science outreach to local high schools, collaboration with international researchers, hosting of an international conference, and continued involvement of undergraduates in chemical research via programs which promote participation of underrepresented groups.Boron-Nitrogen/Carbon-Carbon (BN/CC) isosterism, i.e., the replacement of two carbon atoms with a boron and a nitrogen atom, has emerged as a novel strategy to expand the structural diversity of compounds relevant to materials science. Despite the recent advances in BN heterocycle chemistry, the systematic exploration of BN/CC isosteres of polycyclic aromatic hydrocarbons that have relevance to the development of organic materials has remained underexplored. This research seeks to develop a comprehensive structure/reactivity relationship in BN isosteres of simple acenes. Research plans include: 1) synthesis of the unreported parental BN isosteres of naphthalene and anthracene, 2) characterization of the optoelectronic properties and chemical reactivity of the synthesized materials, and 3) development of a predictive energetic model for BN/CC isosterism of polycyclic aromatic hydrocarbons. Moreover, this research serves as excellent training for graduate and undergraduate researchers in fundamental and applied chemical synthesis. Student participants in this project are exposed to a variety of experimental methods and techniques commonly applied in synthetic organic, inorganic, physical organic, and organometallic chemistry. The interdisciplinary and collaborative nature of the research in conjunction with the outreach activities seamlessly integrates with the education and career development of participating students.