Boron-Nitrogen-Doped Conjugated Aromatic Hydrocarbons

本项目由美国国家科学基金会化学分部化学合成计划资助，由波士顿学院化学系刘世元教授和他的学生合成含硼氮（BN）的多环芳烃（PAHs）。这些分子表现出BN/CC（碳-碳）等构关系，即它们用一个硼原子和一个氮原子取代芳香有机分子中的两个碳原子。虽然含碳碳分子和含硼氮分子的总电子数相同，但它们的性质却大不相同。bn取代的多环芳烃可用于许多应用，包括药物化学和将光转换为电的装置。刘小组正在开发新的合成方法来制造bn掺杂的多环芳烃。一旦制备好，这些分子就会被检查，看它们与相关的含碳分子的反应有何不同。该计划的广泛影响包括研究生在当地公司的工业实习，在当地高中的科学推广，与国际研究人员的合作，主持国际会议，以及通过促进未被充分代表群体参与的项目继续参与化学研究的本科生。硼-氮/碳-碳（BN/CC）等构，即用一个硼原子和一个氮原子取代两个碳原子，已经成为扩大与材料科学相关的化合物结构多样性的一种新策略。尽管近年来在BN杂环化学方面取得了进展，但与有机物质发展相关的多环芳烃BN/CC同分异构体的系统探索仍然不足。本研究旨在建立简单烃类BN同分异构体的综合结构/反应性关系。研究计划包括：1)合成未报道的萘和蒽的BN同分异构体；2)合成材料的光电性质和化学反应性表征；3)建立多环芳烃BN/CC同分异构体的预测能态模型。此外，本研究为基础和应用化学合成方面的研究生和本科生提供了良好的培训。参与本项目的学生将接触到在合成有机、无机、物理有机和有机金属化学中常用的各种实验方法和技术。该研究的跨学科和协作性质与外展活动无缝地整合了参与学生的教育和职业发展。

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.