Encouraging pi-electron delocalization through boron-based heteroaromatic subunits

通过硼基杂芳族亚基促进π电子离域

• 批准号: 1464798
• 负责人: John Tovar
• 金额: $ 39万
• 依托单位: Johns Hopkins University
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2015
• 资助国家: 美国
• 起止时间: 2015-05-01 至 2019-04-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1464798&HistoricalAwards=false
• 关键词: Encouraging; pi; electron; delocalization; through

In this project funded by the Chemical Structure, Dynamic & Mechanism B Program of the Chemistry Division, Professor John D Tovar of the Department of Chemistry at Johns Hopkins University will develop new classes of boron-based molecular materials that have properties akin to traditional inorganic semiconductors. These organic molecules have emerged as attractive components for contemporary organic electronics, with applications spanning anion sensing, non-linear optics and light-emitting devices. Students in these areas will play critical roles in the future developments both on the commercial and academic fronts. One unusual and attractive element of this particular research program is the training environment it will offer to undergraduate and graduate students. Outside of the training in synthetic organic chemistry requisite for obtaining specific pi-conjugated materials, students will be exposed to optoelectronic characterization methods and will serve as intimate participants in collaborative efforts to make new devices. Under the umbrella of this project, the PI will help to increase participation of women and underrepresented minorities in advanced degree programs through continued support of research opportunities at the graduate and undergraduate level.Boron-based pi-electron materials have emerged as attractive components for contemporary organic electronics. Typical structural motifs through which pi-conjugated organoboranes can be included into organic electronic materials consist of triarylboranes as well as boron-containing annulenes with aromatic (such as formally charged azaborine and boratabenzene rings) and antiaromatic (such as borole rings) character. Lacking on this list are formally neutral boron aromatics such as those exemplified by the borepin ring. A primary scientific motivation for borepin inclusion into organic electronic scaffolds is to understand fundamental issues about how the weak borepin aromaticity would influence pi-electron delocalization and polarization given that these molecules would be expected to maintain high degrees of "cyclic polyene" character yet still provide some degree of aromatic resonance stabilization energy. To understand how these unique conjugation features might be exploited for new materials designs, new borepin architectures with varying degrees of intra- and inter-molecular electronic delocalization will be studied. These borepin scaffolds will be fully characterized electronically to understand their novel aromaticities and polarizabilities, and they will be transitioned into collaborative efforts to explore a variety of organic electronics applications.

在这个由化学部化学结构、动力学机制B项目资助的项目中，约翰霍普金斯大学化学系的John D Tovar教授将开发具有类似于传统无机半导体性质的新型硼基分子材料。 这些有机分子已经成为当代有机电子学的有吸引力的组件，其应用涵盖阴离子传感，非线性光学和发光器件。 这些领域的学生将在商业和学术领域的未来发展中发挥关键作用。这个特殊的研究计划的一个不寻常的和有吸引力的元素是它将提供给本科生和研究生的培训环境。在获得特定π共轭材料所需的合成有机化学培训之外，学生将接触光电表征方法，并将作为合作努力的亲密参与者，以制造新器件。在该项目的保护伞下，PI将通过继续支持研究生和本科生水平的研究机会，帮助增加妇女和代表性不足的少数民族在高级学位课程中的参与。硼基π电子材料已成为当代有机电子的有吸引力的组件。 π-共轭有机硼烷可被引入有机电子材料的典型结构基序包括三芳基硼烷以及具有芳族（如形式上带电荷的氮杂硼杂环和硼杂苯环）和反芳族（如硼杂环）特征的含硼轮烯。 在这个列表中缺少的是形式上中性的硼芳族化合物，例如由borepin环例示的那些。 将borepin包含到有机电子支架中的主要科学动机是理解关于弱borepin芳香性将如何影响π-电子离域和极化的基本问题，假定这些分子将被期望保持高度的“环状多烯”特性，但仍然提供一定程度的芳香族共振稳定能量。 为了了解这些独特的共轭功能可能会被用于新材料的设计，新borepin架构与不同程度的内和分子间的电子离域将被研究。 这些borepin支架将被完全电子化，以了解其新颖的芳香性和极化性，并将过渡到合作努力，以探索各种有机电子应用。